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The Screw-Me Scenario

It had all the signs of a good meeting. And I hate meetings. We were:

• Talking about a product we loved
• In great shape from a feature, quality, and schedule standpoint
• A group that historically did not kick ass
• A group that was kicking ass.

The slides looked great and the dry-run was flawless, so why hadn’t I slept in two nights?

I couldn’t sleep because I couldn’t see the Screw-Me.

You Might Be Lying

There’s an article to be written about the different kinds of meetings you’re going to be exposed to, but for now I want to talk about the executive cross-pollination communication clusterfuck. The point of this meeting is alignment. Big alignment. You’ve likely got several different groups who don’t normally spend a lot of time together being forced to sit in the same room so the execs can compare stories, measure reality, and figure out who is lying.

Before I explain how to get your head around this meeting, I want to talk about intent. Intent starts with a question: “Why does this meeting exist?” If you’re responsible for the presentation in this meeting, it exists because someone hates you.

It’s not personal hate. It’s professional hate and it’s exacerbated by a simple fact of organization: different groups speak different languages. Marketing speaks marketing, Legal speaks legal, and Engineering speaks engineering. There’s a fundamental communication breakdown somewhere in the building and someone is feeling wronged. They’re feeling bullied and since they don’t speak your dialect, they’re complaining up rather than across.

Normally, we deal with these Tower of Babel situations with the direct application of middle management, program managers, and other folks we pay big bucks to sit in meetings and translate between organizations. However, translation has not worked in this case. Someone high up on the org chart is hearing two very different stories and wondering which is true. Story reconciliation is certainly on the top of your list of items to resolve in this meeting, but job #1 is to figure out who hates you.

A Rubber Stamp Affair

For these critical meetings, your goal is to make them a rubber stamp affair. In the week before the meeting, you will have personally vetted your slides with each of the meeting invitees. You will have heard their concerns and made the appropriate adjustments to your deck. When the cross-pollination meeting arrives, your goal is an utter lack of drama and the finishing pronouncement of, “Yeah, we should do that and you know how.”

It never happens like this.

We’re “busy” and we have “things to do”, but mostly we’re “looking forward to blindsiding you with a Screw-Me at the least convenient moment in front of your executive team.”

It’s a disappointing trait of human nature that folks who feel wronged like to exact their revenge by flaunting their knowledge and dishing out the Screw-Me at the worst possible time, but, roll with it, you’re already a step ahead just expecting to be screwed. Besides, your enemy is working more with emotion than content and that will turn into their own personal Screw-Me Scenario at a later date.

Right now, your job is data.

No Guilt, No Doubts, No Fear

Ideas get better with eyeballs and before this meeting goes down, your job is to get as many eyeballs on your presentation as possible. You’re not going to get everyone in the meeting, but that’s not the point. The task is cross-pollination. Casting the information net as wide as possible and incessantly asking:

• Does this make sense?
• What is missing?
• How am I going to get screwed?

I’ve got the Russian Lit Major for vetting my strategy; who do you have? I’m not talking about your boss or your co-worker, I’m talking about the person who can objectively look at your presentation and start poking holes. These people are rare because it’s another disappointing trait of human nature that we often think we’re doing each other a favor by listening well, but then tell each other what we want to hear.

You lose yourself in any significant project. You’ve long forgotten your strategic initial assumptions, but, more importantly, you’ve forgotten what other people need because you’re furiously worrying about the daily tactical fire drills. A fresh perspective is a chance to test your entire idea and find the Screw-Me. You need someone to poke holes. You need to find and fill the gaps, and as each gap is filled, you’re going to build confidence around your pitch because, well, that’s one less potential Screw-Me entry point.

You’re not going to find them all. That’s ok, because in the process of constantly refining your pitch, you’re mentally refining yourself. You’re preparing yourself by seeing each of the different perspectives in your deck,. That improves the chances that you’ll know what to do when someone starts dishing out the hate.

Game On

The meeting’s on. You’re walking in with a head full of data and my hope is that through your constant cross-pollination you are legitimately the most informed person on this particular topic in the room. There’s still work to do.

Size the room. Who is here? What groups do they represent? What do they want? Any unexpected visitors? Really? Why would they randomly show up? Who brought them? What possible Screw-Mes could they represent? Ok, let’s get started.

Carry the room. Start your deck. You’ve got it memorized, right? They can tell this is the 32nd time you’ve done it, right? Good. It’s smooth. You’ve already diffused two Screw-Mes by slide 12. Really well done there. Amanda, you have a question?

Manage the room. Questions aren’t Screw-mes. You can clarify and stay on track. You know that Amanda is going to ask about hard data, right? Don’t let her take over the conversation. Say, “I’ve got your data in the appendix, but let me get through this first, ok?” Yeah, you just shut down a Senior VP. Nicely done. No way you can do that without serious confidence in your preparation. Yes, Tim?

Tim’s got the Screw-Me and you didn’t see it coming. Total left field. Completely valid strategic observation and you don’t have a clue how to answer. Shit.

You will recognize the Screw-Me by the complete silence that fills both the room and your head. That’s the realization everyone is having that you’re Screwed. First, let’s not make it worse…

The Unforgivable Spin

Tim: “Rands, what about THIS?”

I’m a poker player and an experienced meeting surfer, so the room will not immediately know from the look on my face that This has Screwed me, but what I choose to do next will define my ongoing relationship with the room.

There are two options when you are cornered by This. Your animal brain, when cornered, will try to find a way out. You can taste this approach even before you begin. I am going to spin. I am going to talk quickly and confidently about This and I am going to hope that in my furious verbal scurrying they are going to believe I’ve got This handled.

That’s not what they’re seeing or hearing.

This is not your staff meeting where a little verbal soft shoe is going to entertain and delight. These are the execs and no matter how many meetings you’ve surfed, they see straight through spin, they know this dance, and the longer you sit there spinning, the longer you give your boss an opportunity to step in, try to make the diving save, and make you look like a blithering fool.

It takes a little practice to make the correct move when you feel the spin coming. You are going to do three things:

1. Acknowledge the Screw-Me.
2. Admit “I don’t know.”
3. Concretely explain the steps you’re going to take to find out and give yourself a deadline.

You have completely defused Tim. See, Tim was pissed which is why he waited until precisely the wrong moment to throw down the Screw-Me. He wanted to see you spin and make a fool of yourself in front of your management team and what you did with the instant acknowledgement was crush emotion with structured sanity.

You can get lucky with spin sometimes. There are times when you spin so hard that you actually talk yourself into a Screw-Me solution that actually makes sense. But this is rare and unreliable and in my experience this frenetic verbal journey erodes confidence and wastes time.

The only question on everyone’s mind during the cross-pollination clusterfuck is, “Do you know what you’re talking about?” It’s lame that Tim doesn’t speak engineer and waited until precisely the wrong moment to Screw you, but my hope is that through your incessant vetting of your slides that you can deliver the “I don’t know” with confidence. Tim just knows what he’s pissed about and you, through your preparation, can see the entire picture.

A Screw-Me Detection Policy

An aggressive Screw-Me detection policy is, I believe, essential to navigating groups of people. It’s not just constantly knowing the potential worst case scenario in any situation, it’s that you are instinctively always looking for it. When I am looking at any situation, I’m always trying to figure out what sequence of events could occur that will screw me.

This strategy sounds a lot like paranoia and yes, an unchecked Screw-Me detection policy can result in a conspiracy theory lifestyle where THEY are out to GET YOU.

Yes, only the paranoid survive, but paranoia is a lot of work. You can burn a lot of calories worrying about all possibilities, but this is not an approach I recommend. What I’m asking is that you look at specific key events strategically. Step back and look at the whole board. Ask “What sequence of moves is going to benefit me? Can I see what is coming? And how could I get screwed?” because teams which kick ass aren’t just ones that deliver, it’s that they deliver when they’re screwed.

An Aspirational Twitter

Big couple of weeks for Twitter. Biz was on Colbert. Ashton got a million followers and bought a bunch of mosquito nets. Oprah showed up sans shift key. Twitter seems to be on the front page of everything but, curiously, has done nothing functionally interesting. They’re just sitting there keeping the lights on.

Not everyone is just sitting there. Some are wondering, “What’s next?”

Birdhouse (Adam Lisagor and Cameron Hunt)

The best explanation (and compliment) I can give Birdhouse is that it’s just like Twitter — the more I attempt to explain what it is, the less you’ll understand. You’re not really going to get it until you use it, but here goes…

Before I begin, a quick reminder. My opinion regarding tweets can be summarized thusly: “I don’t give a fuck what you had for lunch unless you give me reason.” This colorful opinion has already been well documented in The Art of the Tweet.

Described by its creators as “A Notepad for Twitter”, Birdhouse is precisely the application you should be using if you want to bring some art to your tweets.

Let’s say that art is one part consideration and one part timing. Birdhouse supports both parts by providing a temporary safe haven for your partially formed thoughts.

I’ve got an approximate tweet rate of six tweets per day. That’s my thing. The rate at which I discover tweets varies as a function of time and caffeination, but almost always exceeds the publishing rate, which means I’ve often got a tweet pile-up somewhere. Birdhouse is a perfect place to park a thought or link.

While Birdhouse has a clean, usable interface, it’s the act of parking an idea that’s where the innovation lies. Birdhouse separates the act of creation from the act of publication. It replaces the unnecessary rush between “I just thought of this” and “I need to publish this” with calm consideration. This replacement, in my opinion, is essential to developing tweet content of value.

Try it. I know your quip tastes mentally delicious when it shows up, but is now the precise time to share it? Maybe it needs the larger Monday morning audience? Maybe you’ve already unleashed enough of the funny for that day? Your Twitter-schtick is your deal, but my belief is an idea gets better both by letting it ferment as well choosing the right time to open it.

Tweetie (Atebits)

When I first heard of Tweetie for iPhone, I sighed. The problem with explaining Twitter to the uninitiated is, well, you have to say Twitter. A lot. Then you end up saying “tweet” or “twittersphere” or “twoot” and then you flash back to the embarrassing conversation with your Mom when you tried to explain what a blog was.

“No no no Mom… it’s an important thing.”

“What is?”

Sigh. “A blog.”

Tweetie takes dorky, uncomfortable names to the next level. And it does so with stunning visuals and clean interaction design that will change how you use Twitter on your desktop. I mean it.

My measure for compelling visual design is, after installation, whether or not, in the first five minutes, I fire up xScope to see the pixel-by-pixel construction of a particular piece of UI. Exactly 12 seconds after I fired up Tweetie, I was applying the microscope to the breadcrumb bar in Tweetie because I wanted to know “How’d he build that?”

Build products that speak for themselves. It’s simple. The teaser video for Tweetie had no feature lists, it had no spin; it was a simple, kickin’ video with nouns and verbs where using the product was the best pitch. Take a look at the application window below and tell me how many words you can find that describe the functionality. I count one. How many do you count here?

The rest of the real estate is an elegant distillation of the four most important Twitter features:

• Updates — who said what?
• Mention — did they say it about me? to me?
• Direct Messages — only me?
• Search — if they’re not talking about me, what they hell are they talking about?

Twitter has been tidying up the layout of the site to focus on these features, but I don’t want to visit the website — that’s why I installed a rich client. After two weeks of regular usage, Tweetie has eliminated my daily visits to the website by providing simple access to all of the features I need and it does so by borrowing from the future.

Tweetie is a desktop version of an application of the same name for the iPhone which, in my limited experience, is the first time an application has migrated from the phone to the desktop. As a friend mentioned, “Platform merge in progress!” and he’s right.

The navigation in the desktop version of Tweetie feels… like the iPhone. Jumping from Updates to Mentions (via the essential and deliciously obvious keyboard shortcuts) feels like a flick of your index finger. Drilling down on an avatar accesses the user information with a clean horizontal scroll, again, inspired by iPhone navigation.

It’s delightful to navigate Tweetie. The application seamlessly integrates Twitter users, their information, and their conversations into a mesh of information that feels like more than the sum of their parts. And I believe Tweetie, like Twitter, is just getting started. Quick, look at the Tweetie interface and tell me exactly where a future Groups feature lands.

When I use Tweetie, I’m reminded that a maniacal attention to detail not only makes you want to reach out and touch the digitally untouchable, it describes the familiar as the new, and, most importantly, it speaks of an aspirational future.

Keynote Kung-fu Two

You’ve taken some hits. Being taken apart by the execs because they could smell you weren’t prepared. The slide deck you loved that the audience ignored. That guy… snoring. In the front row.

However, you’ve also hit it out of the park. The unexpected standing ovation. That seven-slide deck that turned into an hour of ad-libbed brilliance. The moment you know you’ve deeply connected with your audience.

Admit it, you’ve got some presentation-fu.

The original Keynote Kung-fu article describes how to set up and use Keynote for the first time, but once you’ve done a couple of presentations, you’re going to want more. How To Not Throw Up and Out Loud walk you through the basics of constructing and practicing your presentation, but there’s more to say about Keynote because, as with any well-designed tool, the more you use it, the better you get and the more layers of awesomeness you will find.

Pre-Game

Advanced Keynote Kung-fu starts in pre-game. Before you’ve written a single slide, you need to pick a theme. This process has been simplified in the latest Keynote with the new, ginormous theme picker chock full of interesting templates, but I almost always start with standard black.

I don’t want to worry about anything except the ideas and basic flow. Black is pleasantly generic. The rule is: if you’re starting a presentation by endlessly fussing with your presentation design, you probably don’t have anything to say.

With theme in hand, I follow all of the workspace setup advice I gave in the prior article, including the addition that turns on Master Slides via View | Master Slides. This puts the different types of base slides available in the black template at the top of the slide navigator. Rather than building a custom layout for each new slide, I stick to using this default layout as much as possible for early drafts. There’s a great reason why which I’ll explain shortly.

And then I create slides. Lots of them. More than I’ll ever need. It’s a slide explosion.

I’m an outlining zealot, so I’m going to repeat another piece of advice from the original Fu article. In Keynote’s slide navigator, hitting tab will indent the current slide and create a collapsible group under the prior slide. This simple, convenient feature breaks the linearity of my endless list of slides and is the first indication that I’m headed down an organized path to a well-constructed presentation.

A prior version of Keynote introduced a Light Table view to allow you see just thumbnails of your slides, but this view confuses me. In my head, my deck is linear, with a beginning, middle, and end. While looking at your complete deck is visually stimulating, the wrapping of slides destroys the shape of my deck that I have I my head. The Light Table view is useful only after my deck is done when I’m looking to poach bright ideas for other decks. See?

Organize and Design

The point when organization rather than creation becomes the primary activity is when I start to worry about design and layout. This presentation is far from done, but a design exercise is a great mental break from working on the message. If you haven’t already, take a look at the original Keynote article regarding preparing your workspace. In addition to the preferences tweaks and enabling the color and font inspectors, I enable the following:

• Rulers: you’re going to start worrying about spacing at some point.
• Presenter Notes: as you go through this first part of organization, you won’t be able to ignore the content, and rather than getting stuck endlessly rewriting your deck, use the presenter notes to capture your random inspiration so that you can focus on the organizational task at hand.
• Multiple inspectors: Keynote added an additional mini-toolbar, which includes many of the common inspector options, and I use it a ton, but I still need the inspector window. Actually, I need a couple. Option-Clicking on any of the inspector tabs creates additional windows and I usually have the Slide, Build, and Graphic inspectors open.

With your workspace prepared, let’s begin the deck design transformation. If you’ve stuck with the basic black or any of the base slides for any template, you’re about to discover that you’ve already saved yourself a tremendous amount of time.

Which Master slide did you use the most? I tend to riff on Title & Bullets quite a bit, but the Gill Sans has just gotta go. I also despise the spacing on the bullets, so how do I go back and change the 19 slides that use Title & Bullets? Just change the Master. Typography, artwork, animations, transitions — it can be all be changed at the Master Slide level.

If you ignored my Master Slide advice, you can slap the palm of your hand firmly against your forehead. Like CSS, Keynote slides inherit styles from the Master Slides, and while this is hardly revolutionary, it’s a presentation development must-do to avoid repetitive design tasks. By working with a base set of slides, you give yourself the flexibility to change your mind as much as you want.

Even better, once you’ve developed your personal base set of slides, you can save those slides as a Theme which then shows as up as one of the options in the Theme chooser.

Designing for Failure

At the end of this process, the slides should have a shape and a cadence. Go glance through all your slides. How does it sound in your head? Is it tap tap tap or taptaptappitylet’smovetap? What should it sound like? I don’t know; it’s your deck.

In order to effectively present you need to have a love affair with your clicks. You need to know them intimately not only so you can cleanly step through the slides, but for when something goes wrong. And something will go wrong.

Try walking through your deck backwards and forwards. In your practicing, you’re going to know the regular flow of your deck, but what about when you screw up? I love that multi-stage build-out you’ve got on slide 12 — it’s 32 seconds of transition goodness — but what happens when you accidentally hit Back after it’s done? That’s another painful 32 seconds that you’re going to need to improvise.

Your presentation is not a movie. Each presentation, while structured, is you standing up there waiting for disaster to strike, and when it does, where I want your head at is: “Disaster… failure… is only going to make this presentation better.”

Practicing for the unpredictable, improvising, is covered in How to Not Throw Up, but Keynote also provides a variety of disaster recovery tools.

URL Jump. Available via the inspectors, this feature allows you link any object on a slide to jump forwards, backwards, or to any other slide. My move is to hide these jumps in the navigation of the deck for unexpected moment when I need them.

Presentation Mode. Once you’ve fired up presentation mode, you have a slew of features to help you navigate disaster. All of these features are available by hitting the ? in this mode and here are are few of my favorites:

• Slide Switcher Overlay. You’ve probably already triggered this without knowing because clicking on a number will fire up this handy feature. Just type any number and the overlay will appear.
• Jump to Slide. When you accidentally back up over an animation-rich slide, you can simply jump over the slide rather than stepping through each build using the bracket keys.
• White Out / Black Out. There are moments when you want them to pay attention to you. Keynote provides two features which achieve this effect: white-out (via W) and black-out (via B) do exactly what they describe. Blank the screen with your favorite color so that the spotlight moves completely to you.
• Swap Displays. In presentation mode, X toggles the display and presenter screens while in presentation mode. Handy for those tense first few seconds where it’s not clear which display is showing up where.

Even with adept usage of these tools you’re going to screw-up. I like when a presenter stumbles. I like to see how they react to the unpredictable because non-catastrophic failure humanizes a presentation. I’m there to hear what you think, but when you stumble over that slide and attempt to recover, I get a glimpse of how you think.

A Slice of You

In the past year, I’ve seen two amazing presentations where there was a total absence of slides. One was, essentially, an author reading his essay. Another was two of my favorite people talking about finding your obsession and following it. Both parties, I’m sure, spent a tremendous amount of time constructing their talks, and the results of that work were a scathing critique of Web 2.0 and an intelligent, clever romp into why you should simply focus on building things you love.

You don’t need slides to say something big.

I’m not there yet. Yes, over the past few years I’m finding fewer and fewer actual words on my deck, and I can see a day where I can riff on a single slide for an hour, but I’m not there yet. Not sure if I want to be.

It’s you up there on stage. They paid to see you. If they simply wanted to know what you think, they could have read your weblog or bought your book, but they paid to see you. A presentation is not just the careful construction of your thoughts; it’s a means by which your audience has access to you — pacing, waving your arms, and cleverly recovering from that disaster on slide #32.

Mastery of Keynote can give your deck significant fu, but the slides are a prop. You’re the presentation.

The Pond

“Can I work remote?”

I cringe. It’s Ian and Ian is a senior engineer. He’s a rock. He gets it done. I never have to ask him twice and, after six years, Ian has every right to ask to work remote. But I’m still freaked because my first thought when anyone asks to work remote is, “This fine person is a year away from either quitting or being fired.” Why? Because they’re asking to leave the Pond.

The Pond

When I think of communication in a large group of people, I imagine a pond. Small, round, slightly green water. You can see the edges of this pond and there’s a willow tree over there looking both informed and sad. Metaphorically, all the people in the organization are standing somewhere on this pond. Our positions are based on whom we know and where we are in the organization chart. When something happens in the company, when something noteworthy is said, a drop falls in the pond and creates a ripple.

The ripple is the piece of information traveling from one person to the others. Big drop, big ripple… travels further.

With me so far?

There is a constant flow of information in your company. That means there are constant drips in the Pond, creating various-sized ripples traveling every which way, bumping into each other, and transforming each other into slightly mutated ripples. These mutated ripples are the rumor mill, gossip, and all those small pieces of slightly bizarre information that cross your path during the course of the day.

If you’re in the Pond, you’re gathering data, whether it’s intended for you or not. It’s inevitable. It’s what we do as curious humans; we receive information, digest it, alter it, and then send it on its way tweaked to our own personal wavelengths.

A remote employee is not in the Pond. Yes, he’s on the mailing lists and he aggressively updates the wiki, but the subtle, unintentional, tweaked, quiet information that is transferred throughout the Pond doesn’t leave the Pond. There are those whose jobs it is to look at the Pond and attempt to relay the interesting ripples, but while these program and project managers are well intentioned, they relay poorly because they’re just single observers of ripples. Real information is never conveyed by the individual; we understand by listening as a group.

The group forms a collective picture of the state of the Pond – it’s a distributed picture understood by everyone, but never completely known by one. It is the unspoken royal “we” and this intricate, immeasurable thing is absolutely essential to how a group gets things done well.

Do you mean it?

Remote has to work. It’s not just Ian. There are bright people in your building right now who are going to want to return home to Colorado, and you’re going to let them because losing them is not an option. Also, there’s a planet full of talented people who will always be at a distance, but who represent huge, untapped productivity for your team. Your challenge is how to augment the remote employee’s absence from the Pond.

This article is about how to decrease the risk that you will have to fire your favorite employee who decides to become remote. I’d like to give advice from the other side, on how to work remotely, but I’ve never done it. I don’t have the personality. My professional satisfaction comes from being able to look those I depend on in the eye and ask, “Do you mean it?” There is essential content to be discovered in that stare that will never be fully conveyed in an email, IM, or tweet.

My belief is that without deliberate attention, the remote employee slowly becomes irrelevant to the organization. Through no fault of their own, they can be gradually pushed to the edge of what’s important. And when you’re at the edge, you’re an organizational shudder from falling over it. Failure happens at the edges.

Avoiding failure involves asking four questions before they leave:

1. Do they have the personality?
2. Do they have the right job?
3. Does the culture support it?
4. Do you have a remote friction detection and resolution policy?

The Personality

Whether the employee has the right personality to be a productive remote worker is a tricky call because most of your data about this person is based on working with them. What’s going to happen when you can’t see them? How are they going to react when you forget to include them in the staff call? How are they going to feel when the product launches and they aren’t there to celebrate?

This is what I consider.

Are they eloquent in email? Every bit of communication is more expensive with remote folks, so they’d better be good at it – no matter the medium. Can this person construct and convey a complex argument in a single email? Can this person make an important point… via iChat? Written communication is bereft of much of the intangible value of the Pond. It lacks the nuance of face-to-face communication, which means the author needs to be painfully explicit about the details. Can this person do that?

Are they self-directed? How do they deal with ambiguity? If you’ve given them crap direction, do they bump around for a bit before admitting defeat, or do they immediately ask for clarification? Many of the subtle ways you check in and error correct co-workers leave when they leave. If they’re in the weeds, are they going to ask for help? How long until they ask for help?

How detail-oriented are they? If self-direction indicates how they start a thing, their detail orientation is how well they finish. Is this a person who needs help across the finish line? Do they get lost in nonessential details? When you ask for a thing, are you getting the end result you expect?

How well do they know the Pond? We’ll talk about their job in a moment, but whatever that job is, it will have dependencies on people they are leaving behind. Does this person know how the organization communicates? Do they know both the organizational structure as well as the social structure? Are they asking you who to follow up with or are you asking them? Are they instinctively aware of whom they might piss off and proactively account for this in the first mail rather than after the flame-o-gram?

Do they need the Pond? Knowledge of the Pond is great, but does this person thrive because of the Pond? How much of their day are they spending talking with co-workers? Is this conversation essential to what they do or purely social? Which part of them are you going to socially amputate when they’re no longer in the building?

Are they reliable? I imply at the beginning of this article that it’s a senior employee who has a better chance at being successful remotely, but that’s not true. The ability to work remotely is not entirely a function of seniority; it’s also genetic. There are those who do it better solo. Their standard operating procedure is to simply get it done. Seniority can improve personal efficiency and the quality of the finished product, but I’ve discovered innate reliability at all levels of experience. There are people who simply do what they say they’re going to do.

The Right Job

Typical corporate logic dictates that a remote employee should work on a project that is separable from the rest of the team’s. The reasoning here is flawed. The belief is that the inconvenience of communication and decision-making latency around their distance means they should be separated and placed on non-dependent work.

Every part of that reasoning is wrong. Every part is another reason that remote fails.

My most successful remote employee was a perfect anomaly. He wrote standards — protocols. The heart of his job was to define a structured means of communication where the primary goal was the removal of ambiguity. He was a phenomenal communicator. He went out of his way to completely and promptly answer every email. 24 hours a day. When he visited, he took the time to do a complete circumnavigation of the Pond, vetting all the ripples he could find. He instinctively knew that the skill in defining a protocol is creating a structure that is going to meet the needs of right now, but also the unimagined needs of five years from now. And he applied that not only to what he wrote, but also to how he worked. He was a wonderful anomaly and he taught me that a remote job must be perceived, in all ways, as equal to a local one.

There should be absolutely no consideration of a person’s location on the planet Earth when considering the work you need of them. Each time the concern “Well, they’re remote” comes up, you need to turn the concern around and ask, “What about my company, my people, or the work makes remote an issue?” because that is what needs to be considered locally.

The Culture

How are those back in the Pond viewing the remote employee? The means by which Pond-based employees discriminate varies from the discreet to the direct, from the passive to the aggressive. The reason for this discrimination always boils down a single, fundamental tension: remote creates productivity friction.

The friction sounds something like this:

• “I don’t know what the hell this remote person is doing, so I’m going to assume he’s stumbling around the house in his underwear.”
• “This remote person is messing with my deadline or deliverable.”
• “He doesn’t answer his email.”

How long does it take to build a thing of quality? There’s a cost and the question is how is the remote worker affects this cost. Anything higher than the cost of a local employee creates friction. What was a 27-second walk down the hallway to yell at Bob about his crap code is a now 30-minutes constructing an email. Staff meetings start with a wasted 10 minutes trying to get the videoconferencing to connect. Every single communication with a remote worker costs more and generates more ripples in the Pond, and both their job and yours is to either make this cost go away or justify it.

Respect comes from knowledge and the question is: does your culture support a constant and consistent flow of knowledge to and from the remote worker?

Let’s find out:

• Have you created or implemented specific communication media for the team? Wikis? IRC? Are they used? Do different teams need different media? Are there too many and, if so, how are you going to anoint the one true medium?
• Other than the job, how are you encouraging other random interactions between local and remote folks?
• How often are you seeing these remote folks face-to-face? My vote is at least monthly.

Friction Detection

Remote friction is going to crop up. Just like interpersonal tensions randomly appear in the building, so does friction around remote employees. What are you doing not only to detect these, but also fix them? An example.

I hate meetings, but the brilliant thing about a meeting is that it’s full of people, and in a room full of people you never quite know what the hell is going to happen. The knee jerk reaction to bridging this meeting gap when there are remote workers is always, “We need good video conferencing software.”

After 10 years of hearing this argument, I’m calling fail. Video conferencing works when you need to talk to your kids during that trip to Chicago. It fills that visual gap, but all of the video conferencing solutions I’ve been a part of relative to a meeting create friction rather than remove it.

Yes, I can see Anne on the screen, but she’s flat. She’s also got this 1/10th of a second lag on the conversation, which doesn’t sound like a lot until you’re in the middle of that strategic rant about design and Anne chimes in, mid-sentence, with a bright thought that completely disturbs the creative cadence of your rant. That 1/10th of a second. Her inability to inject her essential thought at precisely the right moment. These micro-disturbances of the Force are a constant reminder that Anne’s not there. She’s being projected on the conference room wall like a well-intentioned screen saver. This isn’t just hurting the tempo of the meeting, it’s eroding her credibility.

In this case, surprisingly, less technology, rather than more, is better. Skype’s proximity to my computer and the usual lack of lag is far superior to video conferencing for 1:1s, and spending a little money on a quality Polycom is a fine solution for the staff meeting, but technology is a tool and never the answer.

Friction detection is paying attention to all the ways a remote employee interacts with the group and constantly asking, “Is this working?”

Another Pond

You, as the manager of people, are responsible for making the remote call regarding a person, putting them in the right job, and making sure the culture supports remote people. But the responsibility of delivering while remote is squarely on the remote employee. Yes, a remote employee answers to himself. At four in the afternoon when they run into an impossible problem, it’s almost entirely up to them to develop their plan of attack.

Working remotely isn’t a privilege; it’s work. And it’s the same work we’re all doing back at the mothership… fully clothed… in the Pond.

The Makers of Things

In the late 1800s, the Brooklyn Bridge was built with no power tools, no heavy machinery, and only a basic, evolving understanding of how to make steel. It’s not these facts, but the stories surrounding the facts that inspire me when I take a good, long stare at a suspension bridge. But first…

Stunning.

In a good bridge, I see the defiant end result of how some of my favorite engineering stories begin:

• “I’m sure you can arrange an impressive line of people who say it’s impossible. I take personal joy in ignoring those who say no.”
• “Yes, halfway through this project we’ll discover the impossible, but we know how to build through the impossible. Impossible is when we do our best work.”
• “Trust me when I say that I can close my eyes and see the end result, and when you can see it, too, you will be amazed.”

Ignore the No. When Brooklyn and New York’s population was booming at the end of the 19th century, the best way to get to and from Brooklyn was via ferries. As solutions were considered, I’m sure there were those who simply thought, “More boats!” These ardent defenders of the status quo were not engineers — they were the business. Their goal was not to build something great, but to make a profit.

It was an engineer named John Roebling who proposed a suspension bridge. We take bridges for granted now, but back in the 1800s, bridges were in beta. They fell. One out of every four bridges… fell. He convinced them by designing a bridge half again as big as any before it that was six times stronger than he estimated it need to be. Roebling designed the complete specification for the bridge in a mere three months and then died of tetanus from an injury he received surveying the bridge site.

Discover the impossible. Both of the towers of the Brooklyn Bridge are in the water of the East River. Ever wonder how you dig a big hole in the bottom of a river bed? In the late 1800s? It’s called a caisson, which is a huge, watertight wooden box half the size of a city block. This monstrosity was constructed on the river, sealed with pine tar, and carefully floated to a specific location on the river. It was then slowly sunk to the riverbed by placing stone on top that would eventually become the foundation.

Done, right?

Wrong. With the caisson on the riverbed, it’s time to push it another 45 feet into the riverbed in search of bedrock. Workers did this through the continued application of stone to the top while workers in the caisson dug out the riverbed with shovels, buckets, and, when necessary, dynamite. There was nothing resembling an electrical grid, so there was nothing resembling modern lighting in this watertight pine-tarred box, which was slowly descending through the floor of the East River. There were no jack hammers, so when they hit rock, they used small amounts of dynamite to crack these rocks. In a pine-tarred box, at the bottom of a river, mostly in a very wet dark.

And when the caisson finally hit bedrock 45 feet underground, they had to do it all over again for the New York tower. 30 feet deeper.

You will be amazed. With his father killed via an accident early in the surveying process, it was Washington Roebling, John’s son, who was chief engineer. He did the balance of this work bedridden in Brooklyn Heights, suffering from caisson disease, which he acquired working in the caisson as it descended into the New York-side of the East River. It’s not technically a disease; it’s decompression sickness or the bends, and it forced him to monitor all of the work from a window in his bedroom. He relayed detailed instructions via his wife, Emily, who effectively managed a cadre of politicians, competing engineers, and anyone else working on the bridge for over a decade.

As the New York caisson descended further than its Brooklyn counterpart, the incidents of the bends increased, killing two men. With no bedrock in sight, Roebling used his knowledge of geology and mineralogy to make an amazing decision: stop digging. It wasn’t bedrock, but it was compacted sand.

The New York tower. 78 feet deep into the riverbed. Resting on sand. It hasn’t moved.

We Are Defined By What We Build

The Brooklyn Bridge was built from 1870 until 1883. A quick history refresher: five years after we finished shooting each other in the American Civil War, we started building this:

Three years after that, work started on another:

And before the Williamsburg Bridge was even done, work started on the Manhattan Bridge:

These are the words and the stories I hear in the Brooklyn Bridge: enthusiasm, audacity, impossibility, and amazement. More importantly, I see a work of bare utility with a palpable sense of confidence, an equilibrium with nature, and a beauty that only grows with time.

We are defined by what we build. It’s not just the engineering ambition that designed these structures, nor the 20 people who died building the Brooklyn Bridge. It’s that we believe we can and decide to act. I’m happy to report our new President agrees when he says,

“In reaffirming the greatness of our nation, we understand that greatness is never a given. It must be earned. Our journey has never been one of shortcuts or settling for less. It has not been the path for the faint-hearted — for those who prefer leisure over work, or seek only the pleasures of riches and fame. Rather, it has been the risk-takers, the doers, the makers of things — some celebrated but more often men and women obscure in their labor, who have carried us up the long, rugged path towards prosperity and freedom.”

Someone, sometime soon is going to start describing the climb out of this impressive hole we’ve dug for ourselves, and they’re going to call it “America 2.0”. Clever, yes. We need a new version of ourselves and that’s going to involve bright, unexpected ideas from those we least expect them from, and they’re going to strike you as impossible. All you need to do to understand these terrifyingly ambitious ideas is to look back at what we’ve already done to understand what we can do.

The Art of the Tweet

In writing an article, I know I’m done when I delete. The process leading to done is chaotic; it’s days, weeks, or months of aggregating writing where I collect and organize paragraphs and sentences. Over time, content creation becomes content shaping as I organize the thoughts into a pleasing coherence.

And then, in a moment, it’s done. It looks nothing like the final product, I still have hours of writing and editing to do, but I know that I’m done because I can see the arc and the shape of the piece. I have a beginning, a middle, and an end, but, most importantly, I have the new ability to remove. I can delete. A line here, a paragraph there — I can let go of things of former importance.

It’s one of the biggest writing lessons I’ve learned in the past few years — the art of less — and the appearance of Twitter has only reinforced this lesson’s importance.

Two Tweets, Three Guidelines

There are two kinds of tweets:

Original material. This is you talking to everyone.

Retweets, quotes, and links. This is you forwarding a thing that you find interesting to everyone. For simplicity’s sake, let’s just call these retweets.

There’s another type of tweet that I want to talk about briefly and that’s the conversational tweet. What does this tweet tell you?

@commanda No clue

Not a thing. As you’ll see with the three following guidelines, my Twitter expectation is that each time I glance at my Twitterstream that I can something of value in any tweet. While conversational tweets are interesting for you and the recipient, they leave the rest of us in the dark.

Say More with Less

Tweet material just shows up. I’m sitting there in someone’s office when they say something which is, well, twitterable. This identification process has become annoyingly front-of-mind over the past year to the point that I interrupt important meetings with the simple declaration, “That’s twitterable”.

With solid twitterable material on my hands, I ask, “Does it need an edit?” The editing of tweets started out as a practicality for me. I needed to know whether or not my rough tweets were more than 140 characters, so I’d fire up WriteRoom, which conveniently counts characters, words, and paragraphs. Yes, I know Twitteriffic counts characters and so does the Twitter web application, but writing happens in big, open places. I don’t like typing in boxes; I want a canvas.

With the rough tweet dumped into WriteRoom, I start cutting. First to get it under the 140-character limit, but, more importantly, to reduce the idea to the basics. The Elements of Style has advice here. They suggest: “Avoid fancy words”. Why utilize when you can use? My advice is similarly confusing: “Drop words to give them room to think”.

In my head, I’m cutting words from my tweet to give you room to mentally add your own:

BEFORE: If it’s 4am, I know how stressed I am.
AFTER: Stress is how well I know 4am.

Nine to seven words. Slight reorganization, but which says more to you?

The act of editing a tweet seems contradictory to the impulsive nature of tweets, which means this is a good time to remind you that I’m a repeatedly stated firm believer that Twitter is what you make of it. I want my tweets with a bit of art. I want each word considered. You want to share the intimate details of your Battlestar Galactica watching habits. Whatever works for you, but how about…

Don’t Say What You’re Doing, Say Why You’re Doing It

The question Twitter asks is, “What are you doing?” I can’t think of the last time that I followed that direction. Fact is 95% of my day would bore the shit out of you. Really. There’s a chance you might derive some meager inspiration from the fact that, right now, I’m sitting in a coffee shop writing — talking to no one — but what is more interesting is why I’m here. Why I choose to do what I do. The tweet is, “Avoiding a meeting I hate”.

It’s just a mental step further from “What are you doing?” It’s a moment of introspection to transform the boring details of your day into delicious group therapy. This is why I think you should…

Add a Bit of Yourself

Twitter is you. I’m a big fan of the retweet, but I have the same fundamental problem with it that I have with literal answers to “What are you doing?” My question about the zero-add retweet is, “So what?”

Yes, the point of the tweet is the link and, yes, I follow some people because they are experts at finding compelling content on the Web that I probably care about. I don’t want just the content; I want to know what you think about it. Retweeting an article? Great, what’s the one line you love? Think that lolcat is funny? Me too, but why?

BEFORE: NYTimes Graphic: Home Prices in Selected Cities: http://bit.ly/4CjL (@khoi)
AFTER: Ouch. Phoenix: http://bit.ly/4CjL (@khoi)

I’ve already got a bevy of sites that are scrubbing and prioritizing the web for me. I check them four times a day and they serve their purpose well. But these sites lack authenticity. I don’t need another list of interesting links.

In Twitter, you follow people, not content.

140

My brief research into the English language revealed the average character count of a word is eight. Throw together a bunch of a smaller and bigger words, some single spaces and punctuation and you roughly end up with the average 140-character tweet being somewhere between 14 and 20 words. Let’s call it 15.

15 words.

In my opinion, the art of a good tweet is not just how much you can convey using extreme brevity, it’s also how you can take an idea, shape it with a bit of yourself, and give it to someone else who, if you’ve given them reason, will do the same.

A Twitter Decision

In starting a significant project, an engineer knows the first three big design decisions you make are vastly more important than the second three.

The nature of these decisions varies from project to project. They may be choices about look and feel, rules about architecture, or trade offs regarding feature set. Whatever these decisions are, they set a tone that defines the success of the project.

When I look at Twitter, I see three early essential decisions about how Twitter allows you to craft a community. I believe much of Twitter’s continued success is due to definition and execution of these decisions.

Interestingly, some obvious candidates for the Top 3, like “Scales like crazy”, “Will generate money”, and “Needs to be searchable” weren’t initially there.

The decisions were:

• Decision #1: A user chooses whom they follow.
• Decision #2: A user chooses whom they no longer follow.
• Decision #3: A user should be judged only by what they say.

These are simple decisions of empowerment. As Twitter’s popularity grows exponentially, both veteran users and recent arrivals need to remember that these basic decisions mean Twitter is yours to build with however you choose.

Yeah, Britney’s here now. Barack was here for a bit. I hear Shaq is figuring out Twitter as well. Yeah, these folks have an inordinate number of followers and are saying nothing particularly interesting, but they do not embody what makes Twitter great. Twitter is great because of choices made to allow you build whatever you want.

Decision #1: A user chooses whom they follow.

This might have been your first Twitter crisis: why am I here?

“Well, I hear so’n’so was on Twitter and I like them, so I followed them so I could figure out what the hell this Twitter thing was all about.”

You added folks. You looked at whom others you respected were following and you added more. Then, someone pissed you off. Someone said something that was not aligned with the vibe of your Twitterstream and you got cranky.

Every couple of weeks, a meme stressing about “an increase in Twitter spam” wanders the Internet. Each time I see this meme appear, I turn away from my keyboard and bang my head against my desk three times.

Twitter spam. Really? Are you even paying attention? I’ll say it again, you choose who you follow. If you’re following a newsbot, you’re going to get news spam. If you follow a good friend who can’t stop RTing, you’re going to to get retweet spam, but complaining about it is like standing the middle of a freeway asking, “Why do these cars keep hitting me?”

“But Rands, I need to follow this person, but they won’t shut up.”

There’s a legitimate complaint here. I’m certain there’s a sensible feature request based on this complaint, like “Please don’t show me tweets contain RT or @” or maybe a feature to put someone you follow on Twitter time-out during that weekend drinking binge where they won’t shut up about their ex-girlfriend. Yes, these features could be added to the base platform, but why complicate a feature you already have? You unfollow. It’s brutally simple and it solves the problem.

Decision #2: A user chooses whom they will no longer follow.

My theory regarding folks who complain about Twitter spam is that they, like me, have been traumatized by decades of email spam. You believe that Twitter spam is inevitable because, well, we lost the war against email spam, so we’re going to loser the Twitter spam war, as well.

You can win this war.

Think if you had the following power over your email inbox. When a piece of spam showed up, you could press a single button and guarantee that you would never receive that type of mail again. Poof. We just eliminated the billion-dollar spam detection and prevention industry with this dream. That’s exactly what Twitter made possible with Decision #2 and they did it with class.

If you choose, you receive a notification when someone starts following you, but have you noticed there is no similar notification when they leave? I find this omission telling. While I can’t confirm the feature omission was deliberate, I hope it was. The simple choice to not broadcast a departing follower strikes me as saying, “We are choosing to focus Twitter’s community conversations on what’s being built, not what’s being taken apart.”

A service like Qwitter quickly appeared to fill the gap, but unless you’re getting paid by your number of followers, getting lost in figuring out why someone is no longer following you is a waste of time. Their departure has nothing to do with you; it has to do with them and the experience they want out of Twitter.

Decision #3: A user should be judged only by what they say.

Take a look at the decisions Twitter made regarding your profile. It’s a spartan, 160-character bio, your location, and a URL. None of which you actually need to fill out. This is decidedly not Facebook. There is no feature in Twitter which tells who in your graduating class has a Twitter account. If you don’t know the person whose account you’re checking out, you’re forced to think. You make a choice to follow not based on where they live, where they went to school, what they do, or whom they know. What matters is what they say.

Yes, this rule says should because there’s no way my hippie utopian vision of a world where bright ideas connect bright people is going to last. Barack hasn’t said much since the election, but still garners thousands of followers a week. Mr. Tweet robotically scrubs your follower list and offers automated helpful advice regarding followers of followers that you might be interested in, and I’ve found some “Well, duh, I should be following them” folks.

Twitter is mainstream and lots of time and energy is being spent analyzing and judging Twitter habits. “He’s got 17,123 followers and only follows THREE PEOPLE. Jerk.” Who cares? Yes, some folks have huge numbers of followers, whereas others have 12. This gives these massively followed people a larger stage for their 140 characters, but because someone has a pile of followers doesn’t mean I ever want my search altered by someone else’s subjective calculation regarding “authority”. I define my own authority. I prioritize.

This is My House

Think of your Twitter account as your house. This is my house. Your house is different. You’re trying to figure out how to use Twitter to monetize eyeballs. Good luck with all that. For me, Twitter remains a place for casual information. For me, a tweet is still a note I tie to a balloon, which I let go and think, “Who is going to read that one?” Sometimes I look and see where it ended up, sometimes I don’t.

In my house, I want to create an illusion of a two-way conversation, which means I continue to prune followers so that content flows at a consumable rate. If I get the sense that I’ve lost control over my Twitterspace, I’ll stop going — the same way my fancy new mail rule files once important messages straight into the well-intentioned To Forget folder.

This is my house and I’m still deciding how I want it built and, thankfully, Twitter decided to be spartan and to stay out of the way. I think they knew the construction of your community is your deal. Bitching about it means you haven’t figured it out for yourself.

Rands in Review 2008

I live in the mountains and in the mountains you need a chainsaw.

Strangely, the time of year it’s the least fun to be outside is when I use the chainsaw the most. This is a result of holiday vacation, trees conveniently falling during winter storms, and short windows of time the county of Santa Cruz allows you to burn in your yard.

The job of the chainsaw is rarely one of actual building. It’s destructive, constructive work where you’re removing dead or live trees in order to make room for others to grow. After an afternoon in the forest, I’m covered in sawdust and sap. I’m bruised, I’m exhausted, and I can barely walk. It’s great.

I’ve been doing the same type of work with the weblog. In preparation for a new design, I’ve been slowly tidying and pruning the site. I’ve also been reflecting on the past year’s writing. Let’s look back at some of my favorite articles from 2008:

Appropriately, 2008 was led off with a Twitter article. Twitter was a recurring theme for the year and it showed up again in May as I talked about what, in my opinion, made a good follower in We Travel in Tribes. The first tweet inspired article was The Quirkbook, which listed a plethora of quirks I gathered via Twitter after admitting a few of my own.

Out Loud was the second half of my reposings on presentations. This article tackled the art of giving a presentation versus writing one. Articles like this appear because of immediate practicality. I was in presentation hell last spring and needed to articulate through my fingers how to prepare for a presentation.

Pixel Rigs documented another visual fascination of mine, namely desktop arrangements. I’m happy to report the Flickr group I created continues to receive a trickle of new desktop set-ups. I’ve recently updated mine, as well.

The FriendDA was an idea that had been kicking around my head that I finally got around to writing and posting. I deliberately disassociated the FriendDA from Rands to see what it could do on its own. Checks of the Twitterstream demonstrate folks seem to find value.

The Coffee Mug Affair was my third obsessive analysis of tools I can’t live without. The “This is seriously fucking black coffee” sits in front of me and is happily serving its purpose as I browse the archives and write this article. The cup also made an appearance on the first piece of Rands schwag, the t-shirt.

The year finished up with this Rands shirt with 100% of the profits go to First Book literacy charity. I’m done printing shirts, but I’ll be leaving what has been printed up in the Buy Olympia store until we’ve sold out.

That’s 23 articles on the year — five less than the year before. Other than some small tweaks, I’m moving into year #4 of the current design — which is unacceptable and currently being rectified.

The fact real work kicks in this week is tempered by the presence of MacWorld, which brings some of my favorite people to San Francisco. This collection of bright minds shows up at a perfect time of year. With the holidays behind us, with the celebration and the cleansing complete, it’s time to ask, “What are we going to build next?”

A Signature Cadence

Early on in the movie Almost Famous, Cameron Crowe constructs one of my favorite getting-to-know-you and let’s-fall-in-love scenes. The lead, William Miller, and the love interest, Penny Lane, stare at each other while lying to each other about their ages:

Penny: “How old are you?”

William: “18.”

Penny: “Me, too. How old are we really?”

William: “17.”

Penny: “Me, too.”

William: “Actually, I’m 16.”

Penny: “Me, too. Isn’t it funny? The truth just sounds different.”

What does a lie sound like? How do we decide to trust? There’s a reason why you can figure out in an instant whether a mail is spam or not. It’s not a single, measurable thing, but a whole set of small, invisible variables with which you can instantly make a judgment — I do not trust this mail.

You have a complex set of analytical mental muscles that help you make critical snap emotional judgments. Whether it’s a mail, a website, or a person, your brain can instantly look at 12 imperceptible aspects of a thing to determine how you should feel.

Truth, love, or lies, human has a signature cadence.

I love Flickr

Really, I love it. My favorite part of designing a presentation is the three hours I get lost slice and dicing the deck and cruising Flickr looking for the perfect image. I always find a photo that changes the way I see my deck.

Flickr pulled my SLR out of my closet and onto my desk. Flickr gives me regular visual insights into friends that I’d never find in Twitter, instant messaging, or even over lunch. I feel as I’ve only begun to scratch the surface of what Flickr can offer and you know what? Until recently, I thought Flickr loved me back. Up until a few months ago, this was the Flickr logo:

As far as I could tell, just about every single Flickr page contained this highlighted message, and what I saw in this simple message was that I wasn’t on a web site; I wasn’t using software. I was somewhere else.

Flickr is not a web site. Flickr is a tremendously large group of people constantly throwing their photos at each other and when Flickr said it loved you, it was reminding you that you weren’t at a website, you were part of a community.

You’re Not a Clock

Some time shortly after Web 1.0 was over, an engineer was programming and making a choice regarding wording. He needed to tell the user how long it had been since something had happened — elapsed time. There are well-formatted, structured ways to display this information, but most assume you’re a clock:

3 days, 2 hours, 12 minutes, 3 seconds.

There are a bunch of problems with this format. First, you waste a lot of space saying very little, but the larger issue is that it doesn’t effectively describe the passage of time. You don’t measure time — you feel it. This engineer understood that you’re a human being. He decided that communicating elapsed time should sound like telling you the time over coffee, “When did Michael update his status?”

It’s small. You probably didn’t even see it. It’s not precise, but tells you exactly what you need to know. Moreover, it sounds like someone rather than something is saying it.

It sounds authentic.

Stop for a second and reread any paragraph in this article, but this time, I want you to listen to the voice you’ve constructed in your head. It sounds like you. This is why, when we meet, you’re going to be confused because I don’t sound like you. You do.

You trust this voice and the more a website or an application is designed to imitate that voice, the sooner a user will engage because they’ll make an emotional connection faster.

It’s a Little Thing

Do this. Take a moment to look on one of your favorite websites or weblogs and look for where they choose to sound like a friend you bumped into at the coffee shop. Once you start looking for it, it stands out. My favorite place to look is at the bottom of the page around the copyright:

It’s a little thing. In the huge pile of work building a website, the words chosen to deliver small messages might seem important, but these small words define a personality and both personality and reputation are built on decisions that feel too small to matter.

Here are three ways JetBlue starts the conversation at their kiosks:

Here’s how Twitter used to tell you they saved your information:

And this is how Khoi reminds you to have a conversation, not a flame war:

This conversational tone has a purpose. By sounding like a human, these small wording decisions push the technology out of the way to reveal what we really care about: the people.

Yeah, they’re faking us out. Yeah, it’s a script that is randomly saying “Hi” in every language possible, but look at the design intent. You are being benignly deceived into believe that you aren’t interacting with a computer, you’re staring through a window at other people.

And that’s where your head should be. Not worrying about how it might work, but who you might find on the other side.

I Think Flickr Still Loves Me

I see a lot of guilt inside the term “Web 2.0”. It’s an overused catchall term used to describe a bevy of new technologies and trends, but what I hear is guilt. When someone uses the term, I hear, “Yeah, so we’re not going to fuck-up and flame-out like those Web 1.0 dweebs. We’re Web 2.0.”

My negative reaction is unfortunate because inside of this guilty morass are some brilliant developments. I enjoy watching the ever-blurring line between a web page and an application. I like seeing the web becoming a cloudy platform.

Mostly, I like the authentic tone that came with Web 2.0.

Who knows who removed the authenticity from the Flickr logo. It’s sad, but it served its purpose. Flickr’s old logo was a quiet efficient invitation to join a community and sound like yourself.

A Pleasant Elsewhere

Tales of a Fourth Grade Nothing by Judy Blume is certainly not the first book I read, but when the question of the first book comes up, it’s the first answer because in my fuzzy thirty-something brain, Tales was the first book I was proud of reading.

I picked it out, I lay on the top bunk of the bed, and I read the book for myself. There was no school assignment motivating my endeavor, just the simple joy of enjoying a book I had discovered by myself.

Summers in the Rands house were full of reading. The Mom signed the sister and I up for a reading program at the local library. The game was “Read as much as you possibly can”. 20 books and you got a patch. 100 and there was some type of pizza parlor incentive. At the start of the summer, I’d walk out of the library with my four new books and think 100 books. That’s impossible.

I’d get home, read the four books before lunch, and start to bug the Mom, “Can we go back to the library? When are we going to the library? I need more books.”

“We were just there.”

“Yeah, but I want more to read.”

It’s these intense summer reading periods that I blame for the four unread books sitting on my desk right now. It’s also the reason for the two packed shelves in my closet of to-be-read books, as well as the stack of seven books next to the bed. My belief is: there can never be enough books.

When I have headache, I read and the headache goes away. When I’m pissed at the world, I find a book and a dark cave and chill in a pleasant elsewhere. Forget about the knowledge and ideas passed along via the written word, reading a book brings a calm to my crazy NADD-driven world.

I see the world in terms of words because whenever I have a quiet moment, I fill it with reading.

My Disaster

Roughly a third of high school graduates never read another book for the rest of their lives, and while there are piles of research that indicates literacy leads to a better quality of life, I simply want to promote a pleasant elsewhere. Certainly, there are more urgent disasters in progress than literacy, but this is my disaster and you can support it.

I offer the first Rands in Repose t-shirt.

This shirt is available in limited quantities until the end of the year.

The simple, yet elegant logo for the shirt was designed by the terribly talented Kevin Cornell. The shirt itself is a product of the Continental Clothing Company and is constructed of 70% bamboo, which sounds freaky until you put it on. Bamboo has a high quality, unique, silky feeling, but is durable and machine washable.

Both men’s and women’s sizes are available in a complex brown color named “bitter chocolate”.

100% of the proceeds for each shirt goes to First Book, a nonprofit organization with a single mission: to give children from low-income families the opportunity to read and own their first new books.

I’d like to thank the folks at buyolympia.com for make the process of finding, printing, and selling shirts easy.

I’d also like to thank the folks who take the time to read and comment on my reposing. It’s my honor to play a small part in your pleasant elsewhere.

Happy Holidays.

Dumbing Down the Cloud

Cloud computing is yet another name for services that have existed for a really long time. Here’s the 2008 IEEE Internet Computing quote regarding Cloud Computing:

“Cloud Computing is a paradigm in which information is permanently stored in servers on the Internet and cached temporarily on clients that include desktops, entertainment centers, table computers, notebooks, and wall computers, handhelds, sensors, monitors.”

Information stored on servers? Temporary caching? Holy fuck. You mean like those email servers and clients I’ve been running for 15 YEARS?

The innovation in cloud computing happened years ago. It happened when some bright engineer was trying, for the 185th time, to draw the Internet on a slide, and thought, It’s this big, huge, amorphous thing that lacks definition. It’s a… cloud.

That’s when the magic happened. That’s when the name mattered. When it was first used to eloquently and visually describe an idea that lacked mental definition.

Everything that has been happening since then is marketing and wishful thinking. It’s those marketing nerds getting paid too much money to rename ideas we’ve already had. Innovation doesn’t come when we give our ideas new names; it comes when the fundamental idea quietly evolves. Innovation often happens silently — not by what you say, but what you do.

Anywhere. Transparently.

My use case for the cloud hasn’t changed in years. I want a single folder sitting somewhere in the cloud that I can transparently access from any computer… anywhere. I’m not greedy; I’ll make it even simpler: I’ll only put documents in that folder. No applications, no preferences, just my well-defined documents.

I’ve been trying creatively-named solutions to this use case for a decade. This is how my technology investigations play out:

• Discover
• Install
• Configure the bits
• Give the solution a whirl three times
• Never use it again.

Fact is, getting me to change my information workflow is pretty hard. I’m a creature of habit and efficiency. While I will compulsively give any new idea or tool a try, an application or service needs to fulfill strict requirements.

Just to grab me, you have to:

1. Make it look and feel like magic.
2. Work flawlessly in the first 10 minutes. If you can’t survive 10 minutes of critical analysis, I’m gone.
3. Provide additional, unexpected awesomeness.

Like I said, it’s tough, and chances are that even if an application meets all of these requirements, I’m going to throw it out because I don’t trust it.

I trust Dropbox. Here’s why.

Dumb versus Smart

There are two approaches to cloud storage: dumb and smart.

A dumb cloud does just what you’d expect. You attach an external drive or you mount a network directory. It’s there. It does nothing unless you remember to manually copy stuff yourself.

A smart cloud combines the external storage with a scheme to do your copying or back-up for you. The idea is that as you change files locally, these changes are detected and sent off to the cloud. Sounds simple enough, right? Brace yourself.

Remember my use case: a single folder sitting somewhere in the cloud that I can transparently access from any computer… anywhere. The key word in that sentence is transparent, and a tool’s inability to be transparent is why applications in this space have been a study in failure. I’ll explain.

The fail begins with you and your two computers: a portable and a desktop machine. You edit one file on your desktop machine. Fine, the bits get sent to the cloud. Then, you make a different change on the SAME file on your portable, which is NOT on the network. Two hours later, you bring that portable onto the network and what happens? You’ve got two different versions of that file which both contain original work. Whatever cloud sync tool you are using will likely ask you: “Hey, both of these files have changed. This one was edited this morning and this one was edited two hours later. Which one do you want to keep?”

It’s a fair question. Sync is trying to be useful, sync is trying to be helpful, but sync is giving you a choice, and while you are generally good at choices, you will screw up. And when you do you will never, ever blame yourself, you will blame sync.

You will twitter: SYNC FUCKING OVERWROTE MY CHANGES, when all sync was doing was what it was told. See, sync will happily screw you if instructed to do so. By you.

Even though it’s my fault, data loss is a colossal disaster in my universe and that means once I figure out data was overwritten, I will not cease my irrational swearing until whatever tool responsible is completely eradicated from my system.

Yet, it is my fault. I chose a solution that was too smart. What I need is for my smart clouds to be dumb.

Dumbing it down with Dropbox

There is nothing new about the idea behind Dropbox. Even the name shows little in terms of innovation. Before I explain how Dropbox gained my trust by solving the sync problem, let’s talk about how it grabbed me.

Is it magic? After a simple install and easy account sign-up on the Mac, you end up with a new menu extra. Choosing ‘Open your Dropbox’ reveals the directory structure of your Dropbox and you’re off. Doing what? I don’t know — whatever it is you do. Folders and files thrown into the Dropbox folder are silently synced with the cloud. On the Mac, unless you look closely, it’s not even clear what’s going on. I had to fire up my portable and set up Dropbox on a second machine to confirm that it was actually doing anything.

The magic of Dropbox is that it doesn’t ask you to think about what you do. You care about one thing: do I have access to the most recent version of my files? And with Dropbox, yes, you do. Wherever you are, so are your files.

A flawless 10 minutes. Once I convinced myself that Dropbox was actually doing something, I pushed it. I dumped a large Keynote into Dropbox on one machine and then jumped to another machine and deleted a different file. How long until everything was reconciled? It wasn’t instant, the Keynote copy was limited by bandwidth, but it worked flawlessly. And besides, you don’t need instant access to your files because you can’t be in two places at once. What you want is to never be bothered by the fact that your files are in the cloud. Dropbox is designed to never get in your way… even when you do something stupid. More on this is in a second.

Unexpected awesomeness. While it wasn’t in my first 10 minutes, the unexpected awesomeness came when a friend asked for a presentation that wasn’t mail server-friendly. He emailed me a link to a shared Dropbox folder, and when I clicked on it, the folder was immediately integrated with my existing Dropbox hierarchy. That’s right, I can construct a complex shared hierarchy in the cloud and you know what that complex collaborative beast looked like? My familiar directory structure.

It’s these types of design decisions where trust begins.

Trust begins when I can see the design intention of an application. What in NetNewsWire, for example, is the end result of endless fretting over every design angle regarding reading feeds. What I expect is that when I’m stumped, its author, Brent Simmons, has not only thought about why I’m stumped, he’s already provided the right feature configured in precisely the right manner to circumvent my stumpedness.

When I use Microsoft Word, I see corporate intent. I see how different warring internal groups tugged the UI to and fro for a decade. I see the intern who did that one feature four years ago. I see a land of misfit toys in the features that haven’t been touched in years.

When I’m using Word, I keeping seeing Word, and I don’t see what I should be seeing, which is what I am writing. When I’m using Dropbox, I don’t even know that I’m using it because it is designed be transparent.

The Screw-Me Scenario

How does Dropbox solve the screw-me sync scenario? To date, Dropbox hasn’t said a thing to me. It hasn’t given me a single decision to screw up. Dropbox is very smart because it never asks you a thing about sync or any file operation. This is the brilliance: Dropbox knows that any question is a chance to make a wrong decision. And a chance to make a wrong decision is a chance to erode trust.

Yes, you can create the conflict scenario. When it occurs, Dropbox quietly creates a conflict file in your folder and lets you figure out what to do. See, Dropbox isn’t going to ask because that’s not the model. That’s not the design. The Dropbox flow is: “We’re not going to bother you with sync because we’re just keeping track of you changing stuff and your stuff is only changing when you change it and there is only one of you. If there’s a problem, you’ll figure it out when you’re good and ready”. It’s not elegant; I still have to eventually go and clean up the mess, but the more you trust a tool, the less you care about the edge cases.

Dropbox is not dumb. In fact, Dropbox is quite smart because it lets me be dumb.

And I’m dumb. Two weeks ago, I sat down to put the final touches on a presentation. I fired up the portable, looked in the usual Dropbox location and it was empty. Ok, well, I saved it to my desktop, right? Ok, no. Maybe another location inside Dropbox? Ok, no. I can taste it’s-deleted-forever adrenalin in the back my mouth now.

Spotlight reveals nothing and I’m starting to blame Dropbox now, so I fire up their web interface, where I discover they keep track of each discrete file operation, and it looks like last night I deleted the presentation in a fit of psychotic folder cleanliness. But here in the Dropbox web interface is every single version of the file that I saved, as well as the ability to restore them.

Click. Restore. And I’m saved.

And that’s smart.

Build Anything

As an engineer, if you want to piss off someone who is asking you whether you can or can’t build a thing, just say, “Given enough time, I can build anything”.

They’ll believe you’re dodging the question, and they’ll think you’re arrogant.

As a means of negotiating a schedule or a feature, this answer is not helpful. You need to take the time to explain your thinking to this person. You need to walk them through your development process. It’s an opportunity to educate and not come off like a jerk.

However.

Given enough time, an engineer can build anything.

I’m optimistic.

And I hire optimists.

Like any profession, software development is chock full of radically different personalities, but I want the optimists. I’m not looking for Yes-folk; I’m looking for those folks who, when backed into a corner with a gun to their heads, respond with, “Fuck it, we’re going to figure it out”.

This base optimism can be hidden in all types of personalities, but when the shit hits the fan it shows up and often creates the impossible.

In my two decades of working in Silicon Valley, I am happy to confirm that this valley is full of these insane optimists. These are people who:

• Work hard
• Over-commit and still deliver
• Rampantly go out of their way to help each other
• Have a track record of stunning success

This is not a population limited to the valley, it’s a population spread across the country and across the globe, but today I’m thinking about my country.

We’re nowhere near the bottom of this disaster we’ve voted onto ourselves. I don’t think the majority of Americans fully understand the severity of our financial crisis. We’re all fervently staring at Christmas, confusing the holiday spirit for hope.

Yet, I remain optimistic.

Regardless of who wins the election, the question remains, “Do we have it in us to re-invent ourselves? Can we rebuild our country into a place we respect?”

Yes, we can.

I live on the west coast of the United States, which is a region pioneers traveled to so they could choose how to define their home, but this whole country is built on that idea — we choose who we will be.

Where I sit, with the cranky engineers —the insane optimists — I hope we all share this optimism because, given enough time, we can build anything.

FriendDA

The lesson of the Holy Shit is that when you stumble upon a truly revolutionary idea, you have the ability to recognize it. There are lots of people who, when they first saw a web page, thought, “I can order pizza on the phone with a live person. Why would I do it on the computer via, what’d you call it? A browser? Also, why is that text blinking?”

You didn’t see pizza. You didn’t even see the blinking text. In fact, you saw nothing in particular; you just had a gut feeling. There was no logic or strategy behind the gut feeling, it was a sense of deep potential. Your amorphous thought was, “I can’t think of anything I won’t be able to do on the web.”

A Holy Shit is the instant of instinctually recognizing massive potential.

As epiphanies go, Holy Shits are few and far between. My gut says you’re lucky if you stumble upon one a year. However, smaller versions happen all the time.

A by-product of obsessively, constantly surfing the net to discover the bright and the shiny is a steady flow of promising new ideas. Mostly slight variations on existing great ideas that tickle your fancy. For example, after staring at Twitter for nearly two years, I’m guessing I’ve had a dozen bright ideas about Twitter-inspired products. These ideas tend to show up in the morning during the drive, after appropriate caffeination, and more often than not they fade the moment I walk into the office.

But some stick.

My rule is: if I’m still thinking about a bright idea when I’m driving home, it’s worth writing down. By passing the idea through my fingers I make it slightly more real… I give it definition.

And then I sleep on it.

The following morning, if I’m still chewing on the bright idea, I start to worry because the logical next step is to pitch a friend. The rule here is: all ideas improve as a function of the number of eyeballs that see them. The troubling converse rule is: as soon as your idea gets out in the wild, it’s no longer yours.

In the corporate world, there’s a legal instrument to protect bright ideas generated inside of the business and it’s called a Non-Disclosure Agreement or an “NDA”. When you sign an NDA for a company, you’re legally saying, “I’ve agreed to take on the responsibility of protecting and not revealing the company’s intellectual property even if that intellectual property consists of ideas that came out of my head in the first place.”

There are lots of interesting variations of the NDA, but the two significant ones are: the Two-Way and the One-Way.

The Two-Way NDA says, “Anything either of us says is private”. The more scary One-Way states, “We can use anything you say, but you can’t use anything we say”.

Neither of these legal instruments is useful to me when I merely want to pitch a friend about my idea. The concept of getting Phil to sign an NDA over a beer while we shoot the shit about my random drive-to-work idea makes no sense. Phil’s a friend.

But I want Phil to know that what I want to chat about is more than our average conversation. I want slightly more than a smidge of ceremony before I spill the beans about my bright idea and I call this ceremony the FriendDA.

The FriendDA is a non-binding, warm blanket agreement that offers absolutely no legal protection. I’d suggest if the idea of legal protection is even crossing your mind that the FriendDA is totally inappropriate for your current needs.

Take a look.

Ideally, the understanding you want to get to with the FriendDA requires only a simple question. The moment you’re about to pitch Phil on the idea you ask, “FriendDA?”

Phil takes a sip of beer and nods.

And you’re off.

The Culture Chart

They played bridge every Wednesday at Netscape. In the middle of the cafeteria. Like clockwork.

The players were a collection of ex-SGI guys and they worked for a variety of different groups at the company, but as I learned a few months later, this core group of men quietly defined the engineering culture of the company… with a bridge game.

Ninety Days

If you follow the rules in Ninety Days, you’re going to have a solid feel for the construction of your immediate team. Who is who. Who does what. What they know. Who the freak is. Who the free electron is. In a start-up when there are only 12 of you, you’re done. You know the people landscape because, from where you sit, you can see them all and you interact with all of them regularly. In a larger company, however, ninety days is only going to give you a brief glimpse of what you need to know about your co-workers, the company, and its culture.

Fortunately, in a large company, tools and documents have been created to help you traverse the culture and process and figure out where people fit. For example, what do you do when you get a random urgent mail from a co-worker stranger? Even if the stranger takes the time to explain who they are and what they do, you still fire up the corporate directory with the simple question: “Who does this bozo work for?”

The corporate directory is the digital representation of a formerly very important document: the organization chart.

A quick glance at the org chart answers a lot of ego-based questions like:

• Which org does he work in? A cool one?
• How many direct reports does he have? More power?
• How close is he to the CEO? More influence?

As sources of information go, the org chart is essential, but it is an incomplete picture of your company, which brings us back to bridge at Netscape.

Bridge

If you looked up the four core bridge players on the org chart, you’d learn a bit. One engineering manager, another guy from some oddly named platform team, another guy who had a manager title, but no direct reports, and the last guy who looked like a program manager.

My org chart assessment: Meh.

What I learned months later was that the folks sitting at that regular bridge game not only defined much of what became the Netscape browser, they also continued to define the engineering culture or what I think of as a culture chart.

Unlike the org chart, you’re not going to find the culture chart written down anywhere. It doesn’t exist. The culture chart is an unwritten representation of the culture of your company and understanding it answers big questions that you must know:

• What does this organization value?
• Who created this value system?
• Given this value system, who contributes high value?
• Who is most aware of how value is being created?

This is fuzzy philosophical mumbo jumbo, so let’s bring it home. In your current job, right now, tell me what it’s going take to get you a promotion.

“I need to work really hard.”

Ok, so you knew you need to work hard to get a promotion before you set foot in your current gig. My question is, what specific thing do you need to do in order to be promoted? I’d argue that for any engineer who is actively managing their career, it’s essential to figure out the answer to this question as quickly as possible, and to do so you need to understand the culture.

Detecting Culture

If you are going to be promoted, you are going to succeed in a group of people when you provide that group things that it think it needs. Now, your gut instinct is that this group of people is the management team, and that’s a good org chart-centric answer. The problem is it’s your job to stay ahead of your manager. You’re not going to get promoted giving your manager what he wants; a promotion comes when you give him what he wants as well as what he does not expect, but desperately needs.

It’s unfair. This guy is tasked with your career development and I am saying it’s your job to tell him what he wants. You don’t have to do this; you can take the reactive cues from your boss, but I derive intense professional satisfaction when I deliver the unexpectedly needed and I discover the unexpected by first finding the culture.

To deduce the culture of a company, all you have to do is listen. Culture is an undercurrent of ideas that ties a group of people together. In order for it to exist, it must move from one individual to the next. This is done via the retelling of stories.

“Max was this nobody performance nerd and three weeks before we were supposed to ship, he walked into the CEO’s office with a single piece of paper with a single graph. He dropped the graph on the table, sat down, and said, ‘No way we ship in three weeks. Six months. Maybe.’ The CEO ignored the paper, ‘We lose three million dollars if we don’t.’ Max stood up, pointed at the chart, and said, ‘We lose ten if we do. We must not ship crap.”

Whether this story is true or not is irrelevant. The story about how Max saved the company ten million dollars by telling the CEO “No” is retold daily. In hallways. At the bar over beers. The story continually reinforces an important part of this company’s culture.

We must not ship crap.

There isn’t a corporate values statement on the planet that so brutally and beautifully defines the culture of a company.

There are other stories that you’re going to hear over and over again, and inside each of these stories are the real corporate values. Each one, while designed to be entertaining, teaches a lesson about what this particular company values, and these are the lessons that are going to get you promoted.

There’s a chance you’re not going to find these stories. My hope is that you’re in a company where engineering is valued and, as such, has an influence on the culture of your company. If it’s been six months, you’ve been actively looking, and no one has told you a great story about how engineering shaped the fortunes of your company, there’s a chance that in your company engineering doesn’t have a seat at the culture table. My question is then, “How are you going to succeed, how are you going to be promoted, where engineering isn’t an influential part of the culture?”

Culture Definers

After you have a healthy collection of stories, you’re going to have a good idea about some of the culture, but you’re still missing essential data for your culture chart. See, the folks who tell the stories about culture usually aren’t the folks who created them.

Stories are told, but first they are born.

The people who are responsible for defining the culture are not deliberately doing so. They do not wake up in the morning and decide, “Today is the day I will steer the culture of the company to value quality design”.

They just do it. The individuals who have the biggest impact on the culture and company aren’t doing it for any other reason than they believe it is right thing to do, and if you want to grow in this particular company it’s a good idea to at least know who they are and where they sit. You need to pay attention to this core group of engineers because as they do, so will the company.

Game Over

Your company is networked in more ways than you can possibly imagine. Just because you’ve reverse engineered the development culture in your organization doesn’t mean you’ve got a complete map of the overall culture. There are endless connections tugging any decent sized group of people in multiple directions at once. There’s the been-here-forever network, the I-survived-the-layoff people, and the untouchable-did-something-great-once crew.

Culture assessment is an information game and it’s never over. Your job is to continually situate yourself in such as a way that, as quickly as possible, you can assess subtle changes in the culture of your company.

I wasn’t concerned when Netscape started losing market share to Microsoft. I didn’t sweat it when the stock price stalled. The reason I started thinking about my next gig was, months before either of these two events occurred, one of the lunchtime bridge team left.

The game stopped. The small group of four no longer spent a long lunch quietly, unknowingly defining the culture of the company and everyone who was watching noticed.

They noticed when one of those who had humbly done the work that defined the company no longer believed enough to stay.

Horrible

I can turn a phrase.

High school journalism is where I discovered this. Mrs. Wickett kept bringing stories to me in my junior year “Needs a clever headline.” I’d read the story and throw out a terse, clever headline.

No clue where this ability come from. If I actually think about how I pick the words and construct the idea, the ability vanishes. The less I know about it, the better.

I’ve been riding this talent for years. Turns out the ability to summarize isn’t only handy for writing headlines; it’s useful in meetings, too. “He just said that, you think this, let’s move on and stop saying the same thing over and over again.”

It was this appreciation of summarization that I took into my first executive product presentation at the last gig. 10th floor of corporate headquarters. Four VPs and their minions surrounding the table. My thought: Wow them with crisp, clean, and clever thoughts. Alliteration. Witty. Headlines.

So I did.

“This is the product. Here are the 20 clever phrases to describe it. Thank you very much!”

Silence. 30 seconds of awkward silence followed by the VP of Marketing breaking the tension, “What exactly are we reviewing here?” The next five minutes were less pleasant as the room realized I was done and all I’d accomplished was filling the air with clever alliterative phrases. There was no obvious strategy behind the headlines.

The Russian Lit Major was standing outside my door as I limped back from the beat down “How’d that feel?”

“Disaster.”

“Yeah, details bore the shit out of you and you suck at talking to executives.”

“… I what?”

I See Bell Curves

You are horrible at something.

You are a bell curve. A standard distribution. At one end of the curve, you have your talents. You’re naturally and uniquely good at them, but you’re not quite sure why. At the other end of the curve, you have your natural deficiencies and, while I am an optimist and I do believe you can learn your way through just about anything, you’re genetically predisposed to be pretty bad at these things.

Now, chances are you are a horrible at a whole bunch of things, but I want to focus on one thing. It’s the thing that will have the most impact on your career. By being bad at this thing, you limit your career growth.

I’m going to make a leap and assume that you’ve already identified your horrible. At some point in the past, you realized you were bad at this thing. “I am unable to read people.” “I love to program, but I am a lousy architect.” “I dress like a goofball.” Whatever your realization was, you become aware that you were deficient relative to the rest of the world, and you took one of two paths.

The first path: you structured your days and your life so that you wouldn’t stumble over this deficiency. Bad programmer, but deeply technical? Ok, you stuck with QA. Unable to read people? Ok, stick with code, don’t manage. Horrible fashion sense? Right so, you’re not first in line for customer visits. As path of least resistance strategies go, this can work. You can sit there and hide from the horrible, but my thought is, if you’re reading this weblog, you chose the other path and you attacked the horrible.

Your thought, “I refuse to suck at this,” so you took the other path and forced yourself to learn through the horrible.

Educating yourself in your deficiencies. Learning. Researching. Practicing. I’m a fan. There is nothing quite like the sense of accomplishment when you know that Darwin is rooting against you. I would go so far as to say that success at overcoming the horrible is far sweeter than success when you know what the hell you’re doing.

And yet… you still might suck at your horrible.

I Want More of You

Back to the Russian Lit Major lurking outside my executive disaster,

“Yeah, details bore the shit out of you and you suck at talking to executives.”

“… I what?”

“You have a product there, but your problem is that you believe that since you can see, everyone else can. They can’t. You need to stitch together the details of how you discovered the product and you need to say it in the language of executives. I’ll show you.”

That night, she took my presentation home and ripped it to shreds. The following morning she sat me down with a completely revised presentation and she walked me through it, slide by slide, pointing out that while I was making fine points, I was skipping over essential details the executives needed to hear. My thoughts were big, but they lacked meat and executive-friendly messaging.

It sucked. It’s one thing to know you’re horrible at the something, but discovery of this horribleness by the rest of the team is a whole other order of magnitude of embarrassment.

Except the slides were better. My messages were still there, but the deck made sense to someone other than me. Two weeks later when we presented again, the questions were enthusiastic, not problematic. I was saying the same thing, but the additions of the Russian Lit Major’s natural ability made my message clear.

Big Trust

There’s a defining moment in your career when you choose to trust someone beside yourself. I’m not talking about trusting them with the small stuff: “Hey, can you fix this bug for me?” I’m talking about big trust “Hey, your design sense is 10x mine, what the hell is wrong with this dialog? Be brutal.”

It’s tricky to leave that swell little island of you. It’s hard to suck up your pride and acknowledge there are those who excel where you suck. But whether you’re an individual or a manager, your job is to learn to scale at what makes you great. Yes, you want to fill your professional experience gaps, but if you work where I work, you’re in a hurry. Getting anything done requires a balance of your natural talent and your ability to find and leverage the talents of those around you.

By putting big trust in someone else, you’re solving three problems: you’re increasing the chance you’ll get your project done, you’re building a strong team, and, oh yeah, you get to watch and learn as someone deftly works in a place where you’re horrible.

By watching someone be great, you’ll learn just like I learned. I don’t need the Russian Lit Major for every presentation, but I know whenever I want to be great, I’ll go and find her.

Impossible

Right now, there’s a CEO standing in front of his 85-person start-up at an all-hands meeting and he’s saying, “In the next 90 days, we need to do the impossible”.

The particular version of impossible doesn’t matter. What matters is that everyone in the room is shocked when he says it. You can tell by the intensity of the silence.

“We’re going to what in the what?”

What gives this guy the right to ask the impossible? Sure, he’s the CEO, but does that mean he gets to stand in front of the room and ask the team to build a levitation machine?

Yeah, it does.

However, this does not mean the CEO isn’t screwing up.

Asking for the impossible is an advanced management technique and it’s one that is particularly abhorrent to engineers. They are very clear on what is and isn’t possible because they’re responsible for building and measuring all the possible. When you ask an engineer to do the impossible, they often laugh in your face not only because they think it’s an absurd, irrational request, they also have the data to prove it.

Yet, given this irrefutable data, I still want you to consider this request. There is an upside to pulling off the impossible. Not only is it a great morale booster, it can also be incredibly profitable, because all your competition thinks the impossible is, well, impossible. Better yet, WHO DOESN’T WANT A FLUX CAPACITOR?

There are three measurements to take with regard to your CEO and his request when the team has been asked to do the impossible. These measurements aren’t going to help you pull off the miracle, but they will help you size the impossibleness.

A Hint of an Insane Plan

First, let’s figure out if your CEO is insane. Listen carefully to the actual request. If your CEO is standing in front of the engineering team asking you to transform lead into gold, you should grin, nod, and start mentally editing your resume, but don’t bolt from the room just yet. Now, if he’s asking you to reduce your release cycle from 90 days to 10, you can let yourself be shocked, but be relieved by the fact that you’re not being asked to perform matter transmutation.

There’s a subtle difference between insane and impossible.

You should respect your gut when that internal “he’s insane” flag starts waving, but that doesn’t mean you should stop listening. There’s more data to gather and there are times where an insane approach might be the right thing.

Our next assessment has to do with legwork. Has your CEO done any preliminary work to actually figure out whether the impossible idea is achievable? What is his strategic intuition about this crazy idea? Is he able to articulate, however vaguely, why this idea is a good idea for the company, and how you might pull this off? You’re not looking for a definite plan, more the strategic broad strokes, a point from which the managers can begin sketching in the details.

A word of warning: there are managers and executives out there who can pitch the impossible on confidence alone. They need no intuition or evidence regarding feasibility to get their teams’ buy-in, and while these chutzpah-laden individuals sure are inspiring, you should trust that nagging feeling that shows up later when you’re driving home, the high fades, and you’re left with a strategic emptiness. That emptiness is the practical result of the CEO’s request lacking everything but confidence. The absence of some thread of an idea about how you’re going to do the impossible, and you might be screwed.

The lack of a glimpse of a plan beyond the charisma translates to a lack of hope.

Skin in the Game

Next, you want to figure out how much skin your CEO has in the game. How much of the company is he betting on this request? If this is a bet the company decision, I’m comforted by the fact that he’s backing this impossible request up with his job. He knows that failure means everyone is looking for a new gig. That’s motivation.

If the request is smaller, if this is a bet the department request, well, the risk is more localized. The cost of failure will likely be born by the senior guys and gals running the show. I’m not suggesting the CEO thinks any less of the importance of this impossible request, but, trust me, he knows that it’s not necessarily his job on the line if the team blows it.

What you’re assessing here are two things: size of the request and level of executive commitment. Having a gut feel for these two things is often a moot point. Depending on your seat on the org chart, you might not even have a chance to choose whether you’re saddled with the impossible. However, developing this swag out of the gate means when the impossible hits the fan you can be one of the first to act.

The Importance of Respect

The glimpse of a plan and confidence. These two fuzzy mental assessments are in play when deciding to ask the impossible, but there is one more that needs to be considered.

Remember, this is an impossible request. This isn’t, “Hey, can you fix these 10 bugs by Friday?” It’s “Hey, can you rewrite this major component in half the time it took you to write it the first time?” Forget whether it’s remotely feasible. Forget whether the confidence is oozing out of every pore of your CEO. You’re not going to be convinced, and more importantly, you’re not going to engage if you don’t respect the person who is asking you to do something

Financial rewards, promotions, IPOs, promises of future interesting projects. All of these incentives matter and can be used to light a fire under a team, but an individual’s decision to engage in the impossible starts with the question, “Do I respect this person enough to tackle the impossible?”

There’s a book to be written about how to build respect in an organization. My brief advice is, when you are asked the impossible, carefully consider every hard request already made of you. Does he ask the impossible every month? Every Monday? Does he follow up on his impossible requests or does he expect you to run with them? Have we ever successfully completed an impossible request? Is he there at 3am on Sunday morning with everyone else, looking like he hasn’t shaved in a week?

I don’t know how many impossible requests you get, but I do know that frequent impossible requests result in an erosion of respect and a decaying of credibility. And that means when the CEO is standing up in front of the troops asking them to perform magic all they’re thinking is, “This crap again?”

What He Really Wants

Nothing I’ve described is concrete. Nothing I’ve described is going to placate your initial intense, negative engineer reaction when your CEO asks you to do something utterly absurd and irrational.

It gets worse… I mean better.

There are times when your leadership should be unencumbered by your version of reality. There are times when it’s important that your CEO isn’t intimately familiar with a product space or lifecycle. Day to day, doing business requires reasonable expectations and an adherence to plans, but those things actually prevent the extraordinary from occurring. The extraordinary requires a catalyst like an impossible request.

What’s important when the CEO asks for the impossible is that he’s pushing the definition of possibility for what the team can accomplish. Maybe your CEO only has an idea, and can only feel the possibility in what he’s asking, but it’s not his job to make it all happen. That’s where you come in. You’re the person responsible for transforming the feel, the intuition, the glimpse of a plan, and the confidence into knowing and doing.

You’re the one who is actually responsible for delivering the impossible, and all I’m asking is that you consider the request, because agreeing to engage in the impossible shatters normality and ignores fears and I love that.

The Quirkbook

It all started with a tweet:

“Making a list of superstitions / foolish consistencies / lightweight OCD behaviors e.g. I always put my RIGHT shoe on first. You?”

This right shoe behavior started during ice hockey. The team was bad… like 0-10 bad. Last game of the season against the best team in the league who slaughtered us in a previous match-up. As I sat in the locker room considering a perfect beat-down of a season, I decided to become zen about situation… deliberate. Rather than stressing about the size of the beating, I considered the small parts of manageable reality sitting immediately in front of me.

“In what order shall I put my gear on? What is practical? What feels right? You know, I like putting my right skate on first. I can’t tell you why, but the order feels important. Right skate, then left.”

We killed them. 9-3. Sure, they started by playing half their game because they were already in the playoffs, but after I scored that hat trick in the first period, they woke up. We slapped them around for another two periods. It was glorious.

I credit the skates. No, I credit the skate application process.

It’s that story that goes through my head each morning as I stare down. I remember deciding to care about how I put things on my feet. It’s a silly superstitious quirk transformed into an unavoidable daily routine and that’s why I twittered it. I wanted to know who else was saddled with these foolish consistencies.

Steven Frank took the time to write me a lengthy mail on my tweet. He mentioned, “For a while I used to semi-believe that if I could tap out a certain rhythm on my desk while the modem was dialing, I’d get through to the BBS instead of a busy signal. Never actually worked in reality.”

I did that, too.

Steven continued, “Anxiety, OCD behaviors, and depression almost always come as a package deal. I’m sure that anyone who reports one has the others. And for some reason, they always seem to affect a lot of folks in tech. I’m not sure which way ‘round the causality is, though.”

There’s a risk with giving a clever name to neuro-behaviorial developmental disorders. I wrote the original NADD (“Nerd Attention Deficiency Disorder”) article expecting the inevitable comment, “You, sir, are making fun of people with legitimate disabilities. Jerk.”

Mostly those comments never arrived. Readers understood the meaning of NADD was not to belittle those with a disability, but rather to see the clever ways we’ve adapted our perceived deficiencies into distinct abilities.

It is with this thought that I present the following responses to my original tweet. I find them informative, sometimes hilarious, but mostly comforting.

• aquarium I hate to be on the left side when going somewhere
• bobthecow i check my zipper every time i walk out of a bathroom. even if i only went in to wash my hands.
• bonsai 1 cup of coffee in the morning. Always. Even when camping in the middle of nowhere.
• borkware I like light switches to be up when on, and down when off.
• brentsimmons I always sit on the right side of the plane, where it’s safe.
• ckolderup volume levels on TV/stereo/etc must be even or divisible by 5
• decafbad Toilet paper rolls go on with paper rolling OVER the roll, not under. Geez, people. ;)
• dreid I make code fit in 80 columns, I delete trailing whitespace, spaces never tabs.
• dstringf Weird quirk - I drop the last word off sentences a lot, especially if I am nervous.
• elaptics putting my hand in my pocket to check that my keys are still there - even if I have just put them in there
• epochblue M&Ms must be eaten in even numbers. You wouldn’t want one side of your mouth to get jealous while the other eats an M&M, would you?
• ergelo always click my pen open twice before writing, it certainly won’t write as well if i don’t
• gooddoug Also, whenever I get a paper coffee cup sleeve, I _HAVE_ to line up the fold with the join in the paper cup. Always.
• hmfullen I can’t resist stacking things, basically any time I’m waiting for anything.
• isaacschlueter I avoid white cars.
• janl Use the right spoon size for the food (complex); when in doubt, a fork. Shoes off or laces lose when coding or sitting comfortably.
• jaredg I always sort the jelly and jam by flavor when eating at restaurants that put the carrier on the table.
• jexner same here - right shoe first. I also try not to step onto broken parts of pavement.
• jtradke must use phone on right ear. even if right hand is needed elsewhere.
• kissane My closet door must be closed at night so nothing can eat my shoes. (We keep neither dogs nor raccoons.)
• kmcg selected eating utensil must be right weight/heft for the moment. (utensils obviously not a matched set.)
• KuraFire car stereo volume in increments of 5; aligning cutlery in restaurants; aligning stacks of things; OH GOD THE LIST GOES ON.
• lfmoliveira must untangle tire air hoses at gas stations (and phone cords anywhere).
• luomat Realized one of my oddities tonight - I will *often* NOT click on the first result in Google until I’ve checked out some of the others
• maczter I always put my pants on both legs at the same time.
• mdhughes All gadgets/tools must go in pockets in the exact right order before leaving home, come out onto desk when I get to work/back home.
• meeju I can’t sleep if not having a mouthful of water before lay down
• melle Browser tabs and task bars have to have their items in specific order, or else they’ve gotta be closed up and re-started.
• nathansmonk When parking my car, I have to have a corner spot.
• naturallygeeky Always push the walk button at crosswalks 10x. That way it knows I’m in a hurry.
• nebulous If one of my feet stumbles/stutters on the ground while walking, I try to replicate it with my other foot.
• nevenmrgan every device light - MacBook, USB hub, TV, clock - must be covered at night. Ambient light is ok, small lights are NOT
• OcelotPotPie I always set my alarm clock in odd numbers. For example, waking up at 8:00AM is an alarm set to 8:01AM. Or 8:59.
• pburleson I don’t get up unless the clock is on a multiple of 5 ( i.e. 5, 10, 15, 20 )
• popthestack I constantly clear my clipboard by copying a single space. I accidentally pasted sensitive things in IM chats one too many times…
• robertpalmer I always wet the toothbrush before putting toothpaste on it. (We started a book of these where I used to work: “The Quirkbook”)
• ryanmears firefox and textmate windows must always be in the same upper left hand corner of my screen, and be the exact same dimensions.
• rynosoft I never realized it until a friend pointed it out, but I tend to sort my fries when eating fast food.
• sandrift Even after I *know* I’ve put my keys into my bag, I must double-check that they’re there before closing car door or trunk. Total OCD.
• simplepixels Checking my pockets repeatedly to make sure nothing fell out. I once had my pocketknife fall out in a pediatrician’s office…
• spotthehall It’s that 1-2-1, 2-4-2, 1-2-1 algorithm - applied to gaps between the pavement slabs…
• ssanchez I knock on subway / Tube doors to ask them to let me on / off, but only if they are the automatic, not push button to open ones
• studlycaps Whenever I see an open cupboard or drawer, I have to close it. I can’t bring myself to leave the room with it open
• tjeremy I have to chew the same number of things on the left side of my mouth as I do on the right side. Even down to color and #, eg: M&M
• zanshin Stairs have to be counted in groups of four.
• ZooFood The join in the paper coffee cup must align with the drinking hole on the lid. Must turn lights off when leave room, close cupboards.

The Coffee Mug Affair

At my favorite local coffee shop, Lorraine gives me shit when I purchase coffee in a paper cup, “You… are not saving the world.”

She’s right. I’m not, and it’s actually worse. Each time I reach for a sip and this sad little corpse of tree flesh greets me with its pathetic weight and palpable sense of Al Gore guilt, I’m lonely.

I’m missing a key member of my creative posse.

A Box Full of Fail

The next chapter in documenting the accessorizing of my obsessions was an investigative report on paper. I’ve got 27 links regarding the history of paper queued up and ready to be read, but I don’t honestly care a lot about paper. I can’t separate the notebook from the paper.

In fact, I’m pissed at paper. Forget about the environmental guilt, cups made of paper are a sure fire way to ruin any cup of coffee because they change the taste. Coffee mugs are the only way to go and I’ve spent a lot more time fretting about mugs than paper. That’s the other thing Lorraine doesn’t know: I’ve got a box full of failed coffee mugs.

Unlike prior excursions, with coffee mugs, we can brief. There is no need for comparison tables. There are just two use cases that define a great coffee mug: Driving and Writing.

Driving

The Driving case is tactical. How do I move from point A to point B without spilling scalding liquid over me and the car? Technology has provided a bevy of James Bondian metal travel mugs guaranteed to safely transport a hot beverage, but this technology comes with a cost. After three uses, like paper, your coffee tastes like whatever material your mug is made of.

This means I’m paying two bucks for the privilege of not being scalded by a cup of coffee that tastes like old aluminum.

No.

Plastic, while less hip, suffers from the same taste degradation over time. Glass-lined or not, three uses and the taste of old coffee and angry plastic permeates every sip. This conveniently leads us to the first key construction point for the perfect mug:

It must be made of ceramic. After years of foul tasting cups of coffee, I’ve discovered a ceramic travel mug, while a hazard if dropped, is the only material that doesn’t affect the taste of the coffee. Combine this with the cleverly designed removable plastic top and you have the Pottery Barn travel mug:

Will it last? I don’t know. Can it survive a drop? Probably not. Will I lose the top? Probably. Does it deliver my coffee as intended? Yes. I have six.

Writing

The Writing use case is strategic because it’s an essential part of my writing process. Right this second, I’m editing this article and, as you might expect, there is a process. First, I sit up. Writing is serious business for which your spine must be straight. I also lean my head slightly downward, looking up at my words as I write. Occasionally I mumble what I’m typing… no clue why.

And then I stop and I take a sip of something from a ginormous coffee cup… which is when I really start writing. The sip of coffee is a pause with weight. As I described in I Don’t Multitask, these moments of silence are invaluable. They are when I step out of what I’m doing to consider what I’m going to do, and for this brief journey I need a companion, and that’s my coffee mug.

To understand this relationship, you have to consider the sip. It’s a conversation and that conversation has two elements:

It must begin with character. The appearance of the coffee cup needs to speak.

It must continue with weight. A full coffee cup is a two-handed affair. The coffee must be blistering hot and a threat sitting three inches to the left of my keyboard. Reaching for my mug is a commitment. It is a reminder that, “Hey, we’re focusing elsewhere for moment. Don’t screw this up. I’m hot.” My coffee mugs are ginormous. My sips — carefully orchestrated.

It’s a brief conversation and it has only one goal: a creative elsewhere.

The Posse

I’m only addressing half of this situation. There’s a coffee bean article to be written, but it’s time to get back to management and design, so I’ll cut to the chase: whole bean + grind at home + French press = FTW.

A great cup of coffee is not just a gorgeous caffeine administration vehicle; it’s part of your creative posse. On my desk, all within a 12 inches my hands, I have the iPhone, the Zebra Sarasa gel pen, a sweetly decaying Field Notes, and the Life is Short coffee mug. None of these items are required for me to write — they are conveniences — but they are essential to accessorizing a moment of creative, companionable silence.

Sweet Decay

I sidestepped the evaluation notebook issue in The Gel Dilemma, but this omission has bugged me because I’ve cared about what I’ve written on for a lot longer than I’ve cared what I’ve written with.

The Mom is to blame here. When I was 10 she gave me a journal entitled “Moments Worth Remembering”. There was a rainbow on front. I asked the Mom:

“What’s this?”

“It’s a journal.”

“For?”

“Writing down what you think.”

“About rainbows?”

The idea had never occurred to me… writing for myself rather than for Ms. Ockerman, the 3rd grade teacher.

Every five years, I go back and reread portions of that journal, looking for the same transition. I start the journal and it’s clear that I’m still writing for school; assuming that someone is going to read and grade my journal. Then, halfway through those pages of horrible cursive, I stopped expecting to be graded and started writing for myself. It was a treatise on the coolness of the Rubik’s Cube and it was just for me.

Since the Rubik’s epiphany, I’ve been writing constantly in journals. During college, I spent two years drunkenly plunking down my thoughts on the computer, but I gradually moved back to the handwritten word since, well, notebook computers weren’t there yet and I wanted to write wherever I damn well pleased.

The Goal

The primary goal of a notebook is to get out of the way… to disappear. It does this by perfectly fitting into your writing situation. How accessible does it need to be? What notebook tangibles do you need? How will it withstand a beating? By fitting into how you write, a notebook becomes invisible. It wastes none of your time because any moment you spend noticing the notebook is a moment you could be noticing something else, and writing about it.

But that’s not what makes a notebook truly sexy.

I have years of experience with some notebooks, weeks with others. As you can see, I’ve explored a wide variety of notebooks. The photo above is ordered chronologically, with my oldest journal on the bottom and my newest discovery, the Field Notes brand, the notebook in which I’m writing the first draft of this article, on the top. Like The Gel Dilemma, I’ve evaluated notebooks according to specific buckets of criteria.

My collection represents a wide variety of the notebooks out there, but they are merely the ones I’ve stumbled upon or had recommended. It is by no means a complete or representative collection. But know this: when I see a store with notebooks for sale, I always stop. I examine. I flip the pages and figure out if there is anything new. I do this regardless of current company, country, or convenience. I am a social introvert, but will stop a complete stranger on the street if they’re sporting an unknown notebook.

Purpose

The Purpose section represents the hard facts regarding this selection of notebooks. As a means of simplification, I’m going to use the word notebook to describe the bevy of different writing receptacles I’m going to evaluate. I could have just as easily used the word notepad, journal, workbook, or sketchbook.

As you can see above from the variety of notebooks I’ve used, there are widely differing intended uses. Anything pocket-sized works better than anything else when you’re sitting on a 16-hour flight to New Zealand. Given that intended use significantly affects value, there is no clear winner regarding Purpose, but there is judgment.

Brand	Size	Binding	Cover	Paper Weight	Pages
Cachet Sketchbook	10.5 x 13.5	Stitched	Hard	Heavy (70#)	~150
Watson-Guptill Sketchbook	8.5 x 11	Stitched	Hard	Heavy (70#)	~200
Moleskin Cahier Notebook	7.5 x 9.75	Stitched	Soft	Medium (20#)	60
Moleskine Reporter Notebook	8 x 5	Stitched	Hard	Medium (20#)	192
Paperchase Notebook	5.75 x 4	Glue	Pleather	Thin (20#)	~250
Moleskine Japanese Notebook	3.75 x 5.5	Stitched	Hard	Medium (20#)	60
Moleskine Notebook	3.75 x 5.5	Stitched	Hard	Medium (20#)	60
Field Notes Notebook	3.5 x 5.5	Saddle-Stitch	Soft	Heavy-Medium (50#)	48
Moleskine Cahier Notebook	3.5 x 5.5	Stitched	Soft	Medium (20#)	64

• Binding is one of those attributes you’ll never notice until it fails. In my experience, sewn binding never fails. I’ve had both glue-based and stapled bindings blow out on me, usually as a result of purchasing an overall poor quality notebook. A blown-out binding means a dead notebook, and that means everything inside of that notebook will be forgotten.
• The Japanese Moleskine has zigzag folded pages with heavier paper. This was novel for about a week and then was totally annoying because I kept forgetting where in the zigging and zagging I was currently writing.
• I love ginormous notebooks with sketch paper. We’re talking MacBook 17” ginormous here. In all-day off-sites with strict no laptop policies, the massive notebook is a security blanket. This is not an everyday notebook, but grab the biggest damned notebook you can find the next time you’re in an art store. It’s a great conversation piece, while also being a handy place to mentally wander when a meeting goes boring.
• Paper weight, the thickness of the paper, is the Achilles heel of many of the Moleskines. While I appreciate the off-white’n’yellow coloring of the paper, the paper itself is thin. I’m guessing 20 pound-ish. This bugs me less than the fact that I can see through the paper to the next page if I’ve already written on it. This is a noisy visual distraction that detracts from Moleskine’s general high quality.

Intangibles and Accessories

Getting into the more esoteric aspects of individual notebooks. These features tend to be where folks start to foam at the mouth with regards to their favorite notebook.

Brand	Lines	Detachable	Color (Cover/Paper)	Availability	Pocket	Band
Cachet Sketchbook	None	No	Shiny Black / White	Art store	No	No
Watson-Guptill Sketchbook	None	No	Matte Black / White	Art store	No	No
Moleskin Cahier Notebook	None	Partial	Brown / Off-White	Everywhere	Yes	No
Moleskine Reporter Notebook	None	No	Shiny Black / White	Everywhere	Yes	Yes
Paperchase Notebook	Grid	No	Shiny Black / White	Borders	No	No
Moleskine Japanese Notebook	None	No	Shiny Black / White	Everywhere	Yes	Yes
Moleskine Notebook	None	No	Shiny Black / White	Everywhere	Yes	Yes
Field Notes Notebook	Grid	No	Brown / White	Mail Order	No	No
Moleskine Cahier Notebook	None	Partial	Brown / Off-White	Everywhere	Yes	No

• I’m fervently anti-line on the page, but for the sake of science, I’ve tried a couple of lined notebooks. The result: yeah, you eventually stop seeing the lines, but read that again, you stop seeing what? I don’t need lines on a notebook. I needed lines in 3rd grade when I was learning how to write. I’m good now, thanks.
• Several Moleskine versions offer detachable paper for a portion of the notebook and this apparently floats some boats, but I never rip pages out of a notebook. I keep the notebooks which survive forever, which means a notebook with ripped-out pages is a violated notebook.
• Notebooks are always black. Sorry brown.
• Inner pockets are like mail rules. By using them, I forget whatever I put into them.
• The elastic band differentiates many of the Moleskines, but it also encourages a curiously annoying habit — you save stuff. The band gives the comforting illusion that your notebook is an enclosure, so you start shoving receipts, postcards, and business cards into the notebook. If packratting information is your schtick, the band helps, but I find once I start packratting, my notebook becomes less a writing tool and more like luggage. This is a mixed blessing as we’ll see in moment.
• There are huge families of notebooks that I haven’t included in my evaluation and the reason is they have too many moving parts. Ring bindings, refillable, tabbed, multicolored, combinable, and linkable notebooks — there’s something for everyone. All I see in many of these features is an opportunity for my notebook to explode.

Sweet Decay

This section was originally titled “durability” because any notebook evaluation must analyze how a notebook is going to survive. We need to understand how a notebook can take a beating because what’s sexy about a notebook is how it survives.

Scars are stories. What I want out of my notebook is that it looks better after three months of beatings. A great notebook decays gracefully. A great notebook weathers its use and becomes more than what it began as. As a notebook is beaten up, its character improves. Therefore, the ratings in this table are different. They explain how, after heavy usage, the various aspects of the notebook survived.

There is additional measure on this table, Character. Character is a purely personal opinion of how the entire notebook looked after three months. As I’m not going to anoint an overall winner, consider Character to be the best gauge of my overall opinion of Purpose, Intangibles, and Decay.

Brand	Binding	Cover	Paper	Character
Cachet Sketchbook	Poor	Good	Excellent	Unremarkable
Watson-Guptill Sketchbook	Good	Good	Excellent	Unremarkable
Moleskin Cahier Notebook	Excellent	Good	Good	Wanna-be
Moleskine Reporter Notebook	Excellent	Excellent	Good	Hip
Paperchase Notebook	Poor	Good	Poor	Embarrassing
Moleskine Japanese Notebook	Excellent	Excellent	Good	Hip
Moleskine Notebook	Excellentt	Excellent	Good	Hip
Field Notes Notebook	Good	Excellent	Excellent	Hip
Moleskine Cahier Notebook	Excellent	Excellent	Excellent	Hip

• There is only one disaster among the nine books, and that’s the Paperchase notebook. No surprise here, it was a Borders impulse buy. It has a thin pleather cover, grid lines, and I was a third of the way through it before the pages just started falling out.
• Moleskine is over-represented in my sample, but that’s because they survived. I’m certain my sample of notebooks would be larger, except that I discarded many notebooks when they decayed quickly and poorly.
• Yeah, there’s an entire article to be written about how the ink lands on the paper.
• The Moleskine catalog is obnoxiously large, but in their quest to be anything to anyone, they’ve found some sweet spots. In particular, I think the small Cahier notebook is a tough combination of cover, binding, and stitching. Yeah, it’s brown, but convenient size and durability makes it my go-to traveling notebook.
• While the decay of the elastic band isn’t listed here, it’s worth calling out that represents a decay paradox. First off, who doesn’t want to be the dude from The English Patient where he’s capturing everything he’s seeing, feeling, and touching in his notebook? I do. The band helps here except when it blows out and becomes a limp black string hanging from my thoughts.

The Whole Story

There’s no obvious winner here because there are far too many uses for a good notebook. For me, notebooks are the home for the primal drafts of my articles. Right now, I’m finishing a draft of this piece on a flight to New York. There are two notebooks sitting in my lap that I’m using for source material because both are my New York notebooks.

How do you want to remember something you’ve done or thought? Your memory, while vast, is apt to alter itself according to your mood, your opinion, the time of day. And it fades and loses things over time. This is why we take pictures. Memory, while often comprehensive in terms of storage, is lousy at reconstruction.

Any context you can capture aids in reconstruction, which is why I write it all down. But better yet, my notebook, through its design, captures context as well. This is why New York looks like this:

There’s a story within a story here. It’s not just what I wrote down, it’s how what I wrote in captured what I didn’t consciously see.

We Travel in Tribes

The rumor that Twitter is abandoning Ruby on Rails comes as no surprise to those familiar with Twitter’s shaky uptime record and its tendency to lose its mind in increasingly impressive and creative ways.

So, new platform. Fine. Saw that coming. What continues to surprise me is this: why aren’t we more pissed when Twitter goes mute for three hours? How about when those tweets you sent just vanished? How come delete only works 50% of the time? Why aren’t the Twitterati bolting to Pownce?

The answer comes down to value. In the time that I’ve been using Twitter, it’s transformed from a curiosity to an essential service. What were seemingly random status updates have now become organized into organic conversational threads that bring a steady flow of relevant content across my desktop.

“Rands, you mean, just like an RSS reader?”

Yeah yeah yeah, that’s not the key value. The value lies in the network of people and how they illuminate the things I don’t know.

Don’t Give Me What I Asked For, Give Me What I Want

When I ask a question, I’m looking for an answer in one of three ways:

1. Specifics. Just answer the question directly and cleanly. I am the king of finding specifics. Average rainfall in Honokaa, HI? Yeah, that took three seconds to find.
2. Like or Related. Rather than answer the specific question, how about a related answer? I’m in a Sigur Ros mood — what should I listen to? Ratatat. Google can help with related answers, but useful discovery rates begin to drop here because relation is subjective. It’s influenced by personal preference — a judgment call. It helps if you know me before you suggest that this is like that and you think I’ll like it.
3. Rock My World. Fuck my question. Rands, here’s a random thing I know you need to know. There is no technological solution to knowing when or how to rock my world. Well, there is, but the technology is far less interesting than the people who use the technology, which brings us back to Twitter.

Affinity is the opposite of Infinity

Twitter is a social network, yes, but it’s a social network without the superpoke scrabtaculous zombie noise and, for that, I’m thankful, because I’ve got work to do. Yes, I could spend days tidying my profile and scrubbing my friends list, but to what end? I want to know more people, and sure, it’s interesting to see what they’re up to, but what I really want to know is what is going on inside their heads with a minimum of fuss.

I want to see how they see the world. This is why I follow people on Twitter. This is why they follow me.

I’ve already described how I maintain a healthy Twitter equilibrium. This lightweight following protocol keeps the average amount of content I receive at any given time to a readable volume and shields me from the increasing and poorly named problem of Twitter spam. As an aside, I don’t understand folks who are complaining about Twitter spam when it’s a fundamental tenet of Twitter: “You choose who you follow”.

There are two immediate networks that I care equally about. First, there are the folks I follow. I actually know or have met a majority of the people on my followed list, but there is also an increasing healthy dose of strangers.

The second list is the folks who are following me. Now, there are functional differences in how these two groups are treated by Twitter and its supporting cadre of third party applications, but, to me, there is no difference between those I choose to follow and those who choose to follow me. Both groups have amazingly high information value because of a simple choice: “By choosing to follow this person, I am acknowledging we may have something in common / an interesting intersection.”

The act of one human being choosing to follow another is a big deal. As long as nefarious intent is not in play, the connection creates what the social science nerds like to call an affinity map; by drawing a line between you and me, we can infer that we’re somehow connected. How are we connected? Who knows? Maybe you like nerd culture? How about gel pens? We’re not really going to know until we test that link by asking a question.

Via the LazyWeb convention, I expect reasonable, informed, and quick answers to most any question. Where I used to use Google, I now use Twitter for questions, because not only do I get the answer, I also get the opinion. And sometimes I get my world rocked with random, psychic, off-the-cuff, tangential information that Google will never give me because Google doesn’t know who I am.

We Travel in Tribes

I’m eagerly watching Twitter evolve and organize itself. I’m dazzled as third parties are giving Twitter memory and context. But what I care about, and what has value to me, is the tribe of people in my ecosystem. Twitter is the best social network out there; it’s a great social search engine; and it’s a short strategic hop from being a terrific next generation address book.

My tribe is not your tribe because you’re not using Twitter how I do. You wrote an Academy Award-winning screenplay, only follow a few people, but have thousands following you. You sell shoes and follow each of the thousands of people who follow you. You are a major airline, but sound surprisingly human.

Twitter’s value has nothing to do with the technology.

Measuring uptime is an interesting nerd exercise, but Twitter’s value lies in how it stays out of the way and allows people to easily connect so they can share their thoughts and, more importantly, explore their differences.

Saving Seconds

I’ve been ripping on the mouse for years.

The argument is one of precision. The mouse, while incredibly useful as a casual means of interacting with a computer, is not a productivity tool, because when you use a mouse you sometimes miss and missing isn’t productive.

WAIT WHOA RANDS. PHOTOSHOP MAN. PHOTOSHOP LOVES THE MOUSE.

Calm down, yes, when it comes to art, to replicating the natural brushstroke, there is nothing better than the mouse (except a Wacom tablet), but do this for me. Go find the Photoshop guru on your floor and watch him or her work. Yes, the mouse is in play, but did you have any idea how much manipulation he did via the keyboard? Want to know why? Because anyone who has a deep, meaningful relationship with a computer is constantly looking for a way to save a few seconds.

The Learning Contradiction

Most of the time when you’re sitting at your computer, you’re doing exactly the same things. Your brain protects you from this mundane observation because your brain is really good at repetition. This is both a blessing and a curse. I’ll explain via an example.

Application switching inside of an operating system is the foundation of NADD. The ability to quickly context switch between apps is so common a task that they’ve developed a keyboard command just for us. In Windows, it’s Alt-Tab, and in Mac OS X, it’s Cmd-Tab. Problem was, when I made the move from Windows to Mac OS X, there was no Cmd-Tab equivalent, so my first moment inside of Mac OS X felt like this…

• “Pretty.”
• “WTF with maximizing windows?”
• “Shit, how do I switch apps?” CLICK CLICK CLICK CLICK CLICK

The pathway I’d learned to do a simple, essential task was blocked. A task I’d taken for granted was now a mental hangnail, which threw off all my timing.

A quick search of the Internet revealed a fine shareware replacement for application switching. After the install of the new system preference, the hangnail vanished. I didn’t think about app switching again. Was my new solution faster? I don’t know. All I know is I’d unblocked the path to do what I needed to do so that I could forget it was there.

The blessing of learning a thing is also a curse. By learning to do a thing, you also forget it’s there, which means as new, improved means of doing things show up, you remain blissfully ignorant. I’m a fan of this ignorance because I’ve got other crap I need to do, and I don’t want to sweat the details, but here’s the rub: the details might be wasting a huge amount of your time.

Saving Seconds

Let’s try a test. From this article, I want you to count the number of discrete steps it takes you to compose a new mail message. Each key or key combination you click is 1 point. A mouse drag is one point. A mouse click is another point.

Ready? Go.

There are two types of people. The ones who waited for me to say Go to compose a new mail and the ones who read “compose a new mail message” and pressed the three keys that are necessary, from anywhere in the OS, to fire up a new compose window.

Anything more than three points to compose a new mail is a massive waste of your time.

“Rands, you are a nerd. I am not. I enjoy the slow gracefulness by which the mouse glides over to my dock and I select the mail application, after which I select the File menu, followed by New Message. Aaaaaaaah.”

All I’m reading is 5 points. All I’m thinking about is the 37 mails you send each day multiplied by 5 points = 185. Let’s multiply that by 30 days in a month, which is 5550 points. Finally, let’s multiply that by the number of other micro-tasks you’re doing where you’re doubling the amount of necessary effort. Ok, I can’t even do the math; I’ve got the productivity shakes here.

Ok, deep breath. Whooooooooooo.

You’re likely not in as a big a hurry as I, that’s fine. You may have an extremely casual, informal relationship with your computer and that’s cool, too. Perhaps this article is not for you, but my question is this: do you want to spend your time heading towards doing stuff, or doing stuff?

This article is for the folks who, when they discover a simpler way to get something done, a shortcut, they get a rush because they know simplicity is elegant and efficiency is a turn-on. The target audience for this article is people who, when presented with some else’s desktop, can’t help but stare and size it up. Their question is, “What is this person doing that will make my world move faster?”

Welcome.

Triage

How many fingers are sitting on the keyboard right now? Go type something. Looks like I’ve got all ten in play, but as I watch myself type, I’m really only using six or so. Yes, my form is crap, but I’m still hitting 90 words a minute on most typing tests.

Would you rather have ten smart fingers or one big, dumb thumb? Ten fingers, of course. Then why in the world are you holding onto that mouse right now?

The first thing we need to do is get you to understand the degree of your mouse addiction, so I’m going to ask you to unplug your mouse. It’s important to leave the mouse in the same familiar spot on your desk, but it must be unplugged.

Ok, now go work for 10 minutes. No cheating.

At some point during these 10 minutes, you’re going to forget the mouse isn’t connected to your computer and you’re going to grab it and the pointer is not going to move. You’re going to think, “Huh?”

Good. Jot yourself a note about what you were doing:

• Switching to Mail
• Selecting Format Menu
• Selecting a paragraph of text

Each of these represents a second or two you can save. Each task that you jotted is a task where some maniacal productivity nerd has already stared at and figured out a way to make it faster. This leads to the second part of your exercise.

For each note on your list, I want you to discover a non-mouse-based equivalent. Start with the local help system. Better yet, let someone else do the work for you and search Google for “Must have keyboard shortcuts for YOUR FAVORITE APP”.

You might not find a shortcut for every task, and even if you do there’s no telling whether that particular shortcut is going to stick in your head, but my guess is… one will stick. It will stick because its value to you will become instantly apparent. I made fun of the Windows Start key for months until the key showed up on my keyboard and I realized it was the simple starting point for EVERYTHING I DID ON MY PC. I’m on a Mac now, but I can still close my eyes and imagine firing up Word: START-RUN-“Word”-Return. Four points… meh. I can do better.

The point of this exercise is awareness. Once you’ve found one or two shortcuts that shave a micro-second here and there, you’ll become more aware of other places where you’re repeating yourself. You’ll start looking for time-saving shortcuts elsewhere because there is bliss in saving time.

Practice Productivity Minimalism

Like your desktop, you’re going to construct your own version of productivity nerdery. Still, here are some of my favorite moves and observations.

As much as possible, I keep my system of shortcuts as simple as possible. My ideal is that I should be able to sit down at any vanilla Mac OS X system and fly. The primary reason has to do with my personality. I’m a nerd and I know that without constraints I’d tweak my productivity system endlessly. I’ll explain.

I recently pinged the Twittersphere regarding how many folks actively maintain their Address Books. As expected, the graph of the responses formed a pleasant bell curve with most folks responding with a healthy “I maintain it as I need it”.

Then there’s the guy who sent me the 700-word email describing, in detail, the precise process he uses to maintain his Address Book. This mail included AppleScripts and shell scripts. I read the whole mail. I ran the scripts, too, because I can appreciate the obsessive nerd personality.

I’m that guy.

I’m the guy who will spend the entire goddamned weekend reorganizing my tagging system because I didn’t like the tone or the tense of my previous tagging system.

Paying attention to productivity is a slippery slope. The system efficiency addiction associated with saving time can become so compelling that your process begins to control more of your time than your product.

Only Essential Additional Tools

Given my minimalist approach, I keep my list of required productivity apps short. In additional to the feverish use of Cmd-Tab for application switching, I also use LaunchBar.

This is the cornerstone of my interaction with the operating system. This is a utility that allows access to just about anything in your hardware and on the Internet via a simple Cmd-Space-application/URL/whatever. Your question is, “Does LaunchBar do my_favorite_task?” And the answer is, “Yes, it does. And if it doesn’t do it out of the box, it’s probably a five-minute configuration exercise to make it happen.” In the past ten minutes, I’ve used LaunchBar to: make a TinyURL for Twitter, search for the LaunchBar website, look up John Adams on Wikipedia, and fire up a half-dozen applications. My favorite game to play with LaunchBar is: “I wonder if…?” where I just start typing “I wonder if…it looks up maps”.

Yeah, it does.

Many folks prefer Quicksilver to LaunchBar and want to argue endlessly about the pros and cons of each. Realize this debate has nothing to do with the strengths of the respective tools, but is merely a manifestation of the zealotry of the nerd personality when it comes to defining, defending, and fretting about the inessential details of their favorite tools.

There are a bevy of other tools you can obsess over. TextExpander is popular with heavy email users in my crowd. There’s also a healthy sprinkling of AppleScript on most of my friends’ desktops. Everyone has his or her own system for productivity, which leads me to my last thought.

We’re All Wasting Seconds

This is the presentation I want to see at the next conference: in a room full of people, anyone is welcome to walk up to the mic and plug their laptop in to the projector. They’ll be asked to complete three simple tasks:

1. Send a mail to a friend
2. Find something on the Internet
3. Save a bookmark or an image.

I would be fixated.

After the presenter was done with the tasks, we’d be able to pepper them with questions: “You did that too fast, what were you doing?” or “What haxie are you using on your dock?” or “I smell AppleScript… what the hell was that AppleScript?”

If each speaker had five minutes, in an hour we’d have 12 different speakers doing the same tasks completely differently, and I promise you’d find a small fix that you’d forget immediately that would forever have added a few seconds to your life.

The Business

You’ve had a small number of career defining moments. These are the select few moments in time when the trajectory of your career changed instantly and drastically. I have two buckets of these: ones I expected and ones that completely blindsided me. While the surprise and subsequent scrambling involved in being blindsided are chock full of delicious adrenaline, I highly recommend the moments you can predict.

One such predictable moment is the first glimpse of the offer letter for your new gig. This is the culmination of hours of resume tweakage, a series of phone screen gymnastics, and two grueling days of in-person interviews. This is the moment where you can answer the question, “How much do they think I’m worth?”

Fact is, you should already know. You’re the business.

Pre-Game

The offer letter negotiation process starts earlier than you think. Think back to your first phone screen. The recruiter was asking you warm-up feeler questions like, “Why do you want to leave your current gig?” and “What’s your ideal job?”, when they slide in a casual, “So, what are you making now?”

You stop. You sense that this seemingly off-the-cuff question is important. Your inner dialog goes something like, “I’m making 64k, buUUut, I’m going to round up to 70k because, well, I’m worth it.”

Yes, you are, but it’s a lie and it’s not a very good lie. You also broke the number one rule in negotiation: be informed. You don’t make 70k; you don’t make 64k, either. You make closer to 90k. HOLY RAISE RANDS.

I’ll explain where this magical raise comes from as well as the other rules in a bit, but first let’s understand how to answer the question “What are you making now?” Your answer: “I’m full-time and I’m making 64k. I’m getting a review in October, and my last raise was 4% plus a 2k bonus. I’d be walking away from 500 unvested options with a strike price currently 12 bucks under market, and all of which are going to be totally vested in 12 months.”

Expect an uncomfortable pause on the other end of the phone. That’s the sound of the recruiter furiously scribbling “Candidate knows their compensation shit” on the top of your resume. What you’re saying with this lengthy informed answer is complex, yet simple. You’re saying, “There are many ways to be compensated. I’m aware of all of them and, when the time is right, I’m ready to negotiate.”

How I’m Doing?

Whether you’re expecting an offer letter imminently or simply wondering how I’m going to make the offer negotiation process entertaining, I have an exercise for you. Let’s figure out what you actually make.

Like frequent resume updates, this career maintenance exercise is designed as a professional checkpoint, which answers the simple question, “How am I doing?”

First, I’ll explain how I calculated your hypothetical yearly compensation above:

• Base salary: 64k
• Benefits: 25% of 64k = 16k
• Bonus: 2k
• Stock: 6k
• Total: 88k

There are two fuzzy areas in this calculation. First, if you haven’t worked for yourself, you probably haven’t considered benefits as part of your compensation before. That 25% is an educated swag that most companies use to account for health and life insurance and 401k. You spend a lot of time ignoring this 25% because it involves things like retirement and health benefits and — duh — you’re immortal. There will, however, be a time, probably sooner than you’d like, that you’ll fully appreciate this portion of your compensation.

The other fuzzy area is stock. This example assumes you got 2000 options when you were hired and these options vest at 25% each year. I’m making an optimistic wild-ass leap and saying that you’re grossing 6k a year using the idea that you are making 12 dollars per option per year. Congrats.

Now, grab a piece of paper and figure out what you make. Don’t sweat perfection. You just need to be close.

The Swag

Fast forward. You’ve just finished the second round of interviews. Traditionally in high-tech, the recruiter is the last interview of the day and their job is to get inside your head and see what you think about the gig. They might throw in some compensation questions regarding your current gig as well. My advice is simple: the more they know you want the gig, the less they need to offer you.

And they haven’t offered you a thing yet.

There’s a time and place for negotiation, and it’s not at the end of six hours of interviews on a Friday when you don’t even know if you’re getting an offer letter.

So you wait. You send off a set of references, sit in bed replaying interviews in your head, and send thank you e-mails to the interview team. All professional karma-aligning activities, but what you really need to do is build your own offer letter. Let’s swag it:

Salary

The business model everyone loves is a business built on recurring revenue streams. This is why you can get a good cell phone for absolutely nothing. You’re going to pay for that phone many times over with your monthly subscription of $39.95. You’re still happy paying $40 a month because that feels like a deal, but carriers don’t see $40; they see the $1500 you’re going to spend over that three-year contract.

Your base salary is your recurring revenue stream. It’s your financial life blood and we’re going to spend a lot of time figuring out how to get it as high as possible because a 1% increase doesn’t affect just this year, it affects every year after it. For the swag, you need to figure out what you want to be paid in the new gig, and my first question is, “For someone doing exactly the same job as you, how much are they being paid?”

For a question that everyone wants to know the answer to, the Internet is surprisingly useless here. In preparation for this article I spent a solid day researching various salary information sites and couldn’t find a single site that contained a job description that remotely described my current gig.

Go ahead and check out those salary info sites and confuse yourself a bit, but I’ve got two pieces of advice for your swag. First, talk to friends with similar jobs. Remember that salaries for similar jobs vary greatly depending on the industry, geographic location, and specific company. Second, take your current salary and add 10% — that’s your salary swag.

Title

Titles, like salaries, vary from company to company, but what you’re looking for in a new job is a sign that you are growing. Associate software engineer now? Ok, drop that associate title from your business cards. Stuck as a software engineer for three years? I’d be looking for that senior prefix when I jumped ship.

Think of your new title like this: what title needs to be added to your resume for this new job to demonstrate that you’re actively growing in your career?

Sign-on Bonus

It’s difficult to swag a sign-on bonus because this type of incentive is often used to augment weak parts of an offer, and you don’t have an offer letter yet. If a recruiter knows you’re keen on stock and that you’ll be disappointed with a low-ball stock offer, they might dazzle you with a large sign-on bonus. Sign-on bonuses are one-time cash windfalls that may never show up again. For now, all you need to know is that they’re often a band-aid, and the question will be: what are they hiding?

Stock

While representing the largest potential for unexpected financial gain, stock and stock options are also the hardest to swag. Rather than focusing on a hard number here, the question you should first ask is, “How much do I believe in this company?” If your answer is, “I like the company, but I don’t see a lot of growth” then focus your negotiation energy on base salary. If your answer is, “I love this start-up; it’s the next Google” then stock grants are clearly going to play a major role in your negotiation.

In terms of valuing the stock, whether we’re talking about a start-up or an established public company, you’re speculating. For a publicly traded company, take a look at the past 5 years. What’s the average stock price? For the start-up, well, my rule of thumb for stock is no different than a venture capitalist’s success rate. A VC’s expectation is that one out of every ten of their companies is going to hit it big and that will cover the investment for the other nine. My expectation is that one out of every ten jobs will result in a stock windfall. This should depress you.

Any value you place on stock or options is a wild-ass guess, but it’s still an important piece of data. The value you put on stock is a measure of your belief in the company.

The Offer

“… and the team is really excited to have you onboard and we have an offer letter for you.”

And then it lands.

Before we digest what the recruiter is saying, I want to reset your head. Yes, you’ve made it this far. Yes, you want the job. Yes, you love the company. But here’s the reality: You are the business. If you take this gig, I think you should pour your heart into it, but I want you to remember that you’re going to have another five to ten other jobs in your lifetime just like this one. This means that for each moment you spend being pumped about the new gig, you’ll have an equal and opposite moment at the end of the gig where you can’t wait to get the hell out.

Amongst these five to ten jobs that you’ll have there is one constant: you. You’re the one who has to pay rent, ride the subway, buy a condo, get married, have some kids, and build your dream house. Your welfare is not your employer’s first priority. It takes one layoff to figure that out.

You are the business and the one consistent metric business is measured by is growth. A new gig represents a rare opportunity where you can drastically change the trajectory of that growth.

The Counter-Offer

As a hiring manager who has been involved in many offer negotiations, the safest way to get me to ignore any counter-offer is to make it without data.

Recruiter: “The candidate wants a higher base.”

Me: “Really? Why?”

Recruiter: “He just does.”

Me: “Grrrrrrr.”

Negotiation is a discussion of facts. Any counter-offer needs to be constructed with the impression that it’s based on data. “I want a 10% raise because, based on my research, that represents the average salary for this gig elsewhere in the industry.”

Sure, it’s still a swag, but your swag demonstrates effort/research/desire and in an interrupt-driven industry full of bright people racing around doing nothing in particular, I’m a fan of research. It demonstrates that you care about your career and that’s someone I want to work with.

The real problem is…

This Offer Blows

There’s some portion of the offer that is disappointing to you, and everyone involved, including your future employer, would prefer that you didn’t walk in the door disappointed. Let’s fix that.

As I don’t know what your problem is with your particular offer, I can’t advise what you need to say, but here are some common frustrations and a plan of attack.

Lower Base Salary: If you’re staying in your industry and you’re staying at an established company, I can’t see how a pay decrease is ever a positive sign. Yes, if you’re moving to a start-up, you’re going to trade salary for stock. You need to figure out if you’re cool with that.

You wanted a 10% increase and they came back with 5%? Why? Sure, your 10% was a pie in the sky swag, but how is the recruiter justifying this base salary? They’re probably saying something about comparable salaries across the company and how you’d be making more than 90% of the people in your grade. That’s a warm fuzzy, but I call bullshit: you’re in the wrong grade.

But It’s Ok, Here’s a Bonus: If the recruiter is pitching this bonus as a fix for your low base, I call bullshit again. A sign-on bonus, like a bonus plan, is a finicky thing that has a habit of vanishing when the sky falls. You can’t count on them. There’s nothing like an instant pile of money to distract you from the fact that, over the long term, you’re bringing less money home.

Even Better, Here’s a Pile of Stock: How do you value this stock? Sure, for the public company, you have a stock price, but you’re not going to see a penny of that stock for a year. And what about that start-up? Well, did you know they have a stock price, too? They have to in order to give it some sort of value. This is how a start-up values itself when it goes to a VC. They say, “We’ve issued x amount of shares and we believe they’re worth y per share. How much would you like?”

You can ask about this internal stock price. You can ask about how big their pool of outstanding fully diluted shares is and that will give you some data about how much of the pie you’re getting. But here’s the rub: I assume start-up options have zero financial value, but this doesn’t mean they have zero absolute value. Again, your measure of the stock is merely the measure of your faith.

And This is Our Final Offer: If some part of the offer blows and there’s absolutely no way to fix it, you have two options: walk away or find another way to ease the blow. If you can’t walk away, have you thought about:

• Asking for additional vacation hours right out of the gate?
• Getting a start date a month later than they’re asking? There’s nothing like 30 days of work-free bliss to adjust your perspective.
• What their work-at-home policy is? Perhaps Fridays working at home will remove that “I’m not getting a raise” taste in your mouth.
• Perhaps my favorite “This offer blows” move is to negotiate a six-month performance review. You know you rock, but they don’t… yet.

Meh

My single worst gig was one where I got everything I wanted out of the offer letter, but in my exuberance for being highly valued, I totally forgot that my first read on the gig was “meh”. 90 days later, I couldn’t care less that I got a 15% raise and a sign-on bonus. I couldn’t stand the mundanity of the daily work and I happily resigned a few months later, taking both a pay cut and returning my sign-on bonus for the opportunity to work at Netscape.

All of this discussion of compensation ignores a simple question you need to be able to answer: “How much might I love this gig?”

For any new job, you should be able to quickly explain to anyone why the new job is bigger than the last and why you might love it. Whether they believe you or not is irrelevant. You’ve got to believe it because you’re the business.

Nerdfotainment

I was introduced to Ask A Ninja via this podcast. In the podcast, the Ninja complains extensively about the release of Pirates of the Caribbean: Dead Man’s Chest. The gist: “Every single character has their own damned plot line and it’s incredibly hard to figure out what the hell is going on”.

The third movie, At World’s End, only compounded the complexity problem. More characters, more plot lines, and more confusion. I just watched the third movie for the third time and discovered another subtle moment of “Oh, that’s why Calypso said that random thing in the second movie. I get it now.”

Back to the Ninja. His final pitch was: “Movies shouldn’t be this much work”. He’s wrong. Movies can be this hard, especially when they’re designed for nerds.

Nerd Generation Theory

According to my math, there is a huge pile of nerds who are traipsing around their 30s. This is the Apple ][ generation and they’re making some bucks. Financial types call this decade of life “the accumulation years” because, traditionally, this is the time of life when you start gathering piles of cash for use during the rest of your life. You’ve found your ideal gig and you’re hitting your stride.

Advertisers love these 30-somethings because they have large disposable incomes. Consequently, content creators love them as well, which means that for content creators to generate their own piles of cash, they need to develop entertainment targeted at the nerd demographic.

What do we know about nerds? Well, we know a lot. They need a project, are systematic thinkers, and they love puzzles and games. This brings me to a whole pile of entertainment that has shown up over the past ten years. All of which, I believe, is specifically designed for the nerd demographic, since all of the content shares a common characteristic: it’s terribly complex and nerds enjoy making it more so.

J.J. Abrams is a Big Nerd.

One of the more prominent recent examples of nerd entertainment is J.J. Abrams’ Lost. If you don’t follow the show, here’s the pitch: “A plane leaving Sydney, Australia, headed for Los Angeles, crashes in the middle of the Pacific. The survivors end up on a mysterious island where an endless stream of bizarre, unexplained shit goes down.”

I’ve just told you the basic premise of Lost, but I’ve actually told you absolutely nothing about the show. This is because Abrams has constructed a seemingly infinite set of intersecting plot lines involving all the major characters, both on the island and before they got to the island. Combine these elements with the usual science fiction elements such as immortality, time travel, and a creepy black smoke monster and you’ll quickly realize that one of the biggest criticisms of the show is “I have no fucking clue what is going on”.

That’s right. That’s the point. That’s why nerds created the Lost Wiki. That’s why we replay all the trailers in slow motion. We’re looking for that tattoo on the shark in the third episode of the second season because AH HAH! That explains something. I’m just not sure what… yet.

Nerds are systematic thinkers, which means, for entertainment, we want to exercise our systemic comprehension muscles. We want to stare at a thing and figure out what rules define it. In the case of Lost, Abrams get this. He sprinkles hints of systems within the system of the show. He tinkers with time and with personalities to paint brief glimpses of clues. And then he changes everything because he knows that if we ever feel we’ve figured it out, we’ll bail.

Captain Kirk doesn’t know he’s a Big Nerd.

Our search for entertaining complexity is not new; it’s just gone mainstream. In fact, if systemic complexity doesn’t exist in a nerd-appropriate show, we’ll go ahead and create it. Think about the original Star Trek series, which, in my opinion, was one of the first pieces of serious nerd entertainment.

Like Lost, the amount of content and discussion regarding the original series, which hasn’t seen production in FORTY YEARS is mind-boggling. Yes, we’re still arguing about whether Captain Kirk could actually build a cannon to kill that lizard-guy . “In a battle between the Enterprise and a Star Destroyer, who would win?” (cough: Enterprise, duh, Star Destroyers can’t fucking steer.)

I’ve no idea how much backstory Gene Roddenberry constructed behind his characters and his stories. But I know that nerds, with their love of this show, have forced systemic complexity on it. Because if there is no project, no problem to solve, it’s not engaging.

Feluf, also a Big Nerd.

Feluf is my Level 70 Night Elf in World of Warcraft. I was running Karazhan with my guild the other night and I landed two sweet Epics: Ferocious Swift Kicker boots and the Steelhawk Crossbow.

Many of you have no clue what I just said. Some nerd crap about World of Warcraft. If you have no clue whether World of Warcraft would float your boat or not, my question is: what’d you do when you read the previous paragraph? Did you Google Karazhan? How about Epics? If you did, you learned that Karazhan is a dungeon and Epics are apparently really good gear.

Unlike popular TV and movies, World of Warcraft is clearly targeted at the nerd mind set, which means it’s designed with brutal system complexity in mind. Sure, they’ve designed the beginning of the game to be simple and approachable, but that’s how any good drug dealer builds his business: the first hit is free.

Significant engagement in World of Warcraft reveals a world chock full of complexity. You want to stop running all over the place? Well, you need a mount, and those guys show up at Level 40. To get there, you’re going to have to figure out what gear is good for your class. You’re going to have to learn how to make money to buy your mount, either via your profession or via building and selling goods at your local auction house. And once you get your mount at Level 40, you’re already going to know there are faster Epic mounts out there. Shit.

There’s a point where all this complex game drudgery sounds like life, and yeah, there is a lot of social interaction between players and guilds. But it’s intersections within the system to support the system. Warcraft is built to be impossibly complex, but every player is always secretly thinking, “I can totally figure this out”. Which is why Blizzard changes the system every few months.

Kaiser Soze. Unpronounceable Big Nerd.

The Usual Suspects, Memento, and Donnie Darko. These movies represent some of the best of nerd entertainment, and two of these movies didn’t do great at the box office. Yet all of them eventually made a pile of money because of the unique system puzzles they presented. Most folks walked out of those movies thinking, “I’m, uh, not sure quite sure what just happened to my brain”. Whereas we nerds rushed home to the Internet to begin the quest of figuring out the system. IT’S A TIME TRAVEL MOVIE, RIGHT?

We followed that line of questioning up with the immediate purchase of the DVD. In the case of Donnie Darko, this not only made the movie profitable, but also resulted in eventual release of the Director’s Cut of the movie, which only created more mysteries regarding that bunny who is still freaking me out.

Mr. Darcy is a Big Nerd. No, really.

Nerds have no monopoly over mind-bendingly complex plots. Anyone with a girlfriend has already endured multiple adaptations of the Jane Austen classic Pride and Prejudice. Yeah, I’ve been there. Yeah, I know the A&E version is the only adaption worth anything and I further know it’s because of that annoyingly charming Colin Firth portraying Mr. Darcy.

Yes, Mr. Darcy. Like the plots of J.J. Abrams, the arrogant intensity of Captain Kirk, and the devious hidden intentions of Kaiser Soze, Mr. Darcy is great nerd entertainment. I mean it.

Once you get past all the “doths” and “thous”, and realize there’s a lot more going on than social climbing and gold-digging, in Mr. Darcy you find a complex and nerd-worthy character. Why’s he being such an arrogant prick? SHE’S NEVER GOING TO LOVE THAT… WAIT… WHAT?

Argument about the natures and motivations of the characters in Pride and Prejudice might seem different than those in Lost or The Usual Suspects, but ultimately, we’re yelling about them because they are beautifully crafted unsolvable puzzles.

And that’s nerdfotainment.

I Don't Multitask

I’m at the end of a conference week and I’ve just moved hotels. This is normally a hassle, but the broadband in the prior hotel blew, which means I’m a week behind on everything. Once I’ve checked into the room, the first thing I do is fire up Safari and watch the first page load. Nearly instant.

Sweet, sweet broadband.

As we know, high-speed access to the Internet is the key to information bliss in The Cave, but we’re not in our Cave, are we? We’re in New Zealand on the 9th floor of a strange hotel where they tell me the water flushes down the toilet in the opposite direction. I haven’t checked; I’m busy building my Cave away from home.

There are two goals with the process: creating a sense of comfortable familiarity while also managing the interestingness of the surroundings. I start by positioning the desk so I have line of sight to the TV, and then I remove all non-essential, distracting crap from the surface. I turn on the desk lamp and the bathroom light and turn off the rest of the room lights, creating a comfortable blanket of darkness around the desk.

The window stays open unless it’s a significant source of glare. I used to always pull the drapes because I used to see windows as very high-resolution screen savers, which are apt to grab my attention. But, as we’ll see, the interestingness of this natural screen saver outweighs the risk.

Lastly, I need mental background noise to tap into when I’m not focusing on whatever task it is I’m working on. Back at home, my favorite source of white noise is the coffee shop. It’s chock full of people, stories, and familiar, random sounds that fuel my creative forward momentum.

No coffee shop here, so I need to create it. A movie will work, and I get lucky and find Casino Royale, which I’ve already seen.

I spend the next hour and a half doing tasks that don’t require significant attention. I’m scrubbing email, scribbling random thoughts, triaging bugs, tidying articles in progress, and generally doing tasks on the B list. What’s more interesting are my mental breaks. I jump into another tab in Safari and take a glance at del.icio.us, Digg, Google Reader, or other meta-content. I watch the movie for a few moments or glance out the window to see what the world is up to.

These mental breaks share a common trait: they provide rich content, but not rich enough content that I’ll stop working on my B-list tasks.

When Casino Royale is over, the next movie comes on, which is The Majestic, with Jim Carrey. This presents a potential problem. I haven’t seen this movie, and I don’t want to risk it being good and grabbing my attention.

No problem. Wikipedia to the rescue. I spend five minutes reading the plot of The Majestic and I’m done. The summary describes all the plot twists and aspects of the movie that might grab my attention. Reading the Wikipedia summary lobotomizes the interestingness so that the movie becomes structured white noise. I can glance at it for 5 seconds, take my mental content break, and not get lost in wondering where the movie is going because I already know how it’s going to end.

The World is Not a Screen Saver

In Malcolm Gladwell’s The Tipping Point, he describes how researchers for Sesame Street determined what parts and how much of the show were actually registering with five-year-old kids. What they discovered was that, when presented with toys and quality segments, these children were able to play with toys and remember content from the show just as well as kids who just watched the show.

This research from the late 1960s contradicts a lot of the bitch-slapping directed at multitasking, especially in the recent Autumn of the Multitaskers article. The article summarizes, “we concentrate on the act of concentration at the expense of whatever it is that we’re supposed to be concentrating on”. This article goes on to say that multitasking-related stress prematurely ages us, hampers our ability to focus and analyze, and, in the long term, causes our brains to atrophy.

Compelling stuff. I especially like the reference to one of the studies where “… researchers asked a group of 20-somethings to sort index cards in two trials, once in silence and once while simultaneously listening for specific tones in a series of randomly presented sounds.”

Knowing how important having a properly constructed Cave is to me, both at home and remotely, the phrase “listening for specific tones in a series of randomly presented sounds” stands out. Think about how the task of listening for specific tones amongst noise would fit into my Cave environment. The answer is: it wouldn’t. In fact, it would drive me batshit crazy and I’d chase the researcher out of my hotel room with a broom or whatever the hell they call a broom in New Zealand. Of course the students listening for tones in random noise learned less; the researchers were bugging the shit out of them.

The Autumn of the Multitaskers actually leads with a story about how the author crashed his car trying to use his cell phone while driving. He implies, but does not explore, the idea that multitasking is a skill and not a generational curse. The hidden contradiction in the article is that you could just be really bad at multitasking. And my guess is that being really bad at anything you need to do often is potentially a recipe for stress and early aging.

It also reminded me of another thing: I don’t multitask.

Multitasking is a convenient descriptive term for what I do. In fact, to the outside observer, multitasking is a perfect description, but because it’s based on outside observation, it’s misleading.

I don’t multitask. Think about it, you can’t concentrate on two things at once. Yes, to the outsider, I am doing many tasks at once, but in my head I can only do one thing at a time. Where the art is, where the skill is, and what the term should describe is what I do between the tasks. What I do well is a combination of timely, adept context switches combined with content-rich breaks. It looks like this:

And it feels like this.

I deeply consider the thing I’m working on. I sit up straight, furrow my brow, talk to myself, and dig into what I’m doing. My environment is meticulously designed to support this, whether it’s the precise, familiar location of my computer, the blanket of darkness surrounding me, or the white noise I select to provide a mental break focal point.

At some point while working, I will reach a mental block. I quickly assess the magnitude of this block (minor cramp or total fucking blockage?) against the priority of the task (need to finish this now or whenever?) Based on that lightning fast assessment, I either stop or grind it out.

This stop may be a context switch to another task, but it’s often a break to soak in the white noise, and it’s in these pauses that I’m brutally creative. When I stare out the window of the hotel, I see a small harbor full of sailboats, and, somehow, the haphazard arrangement of the colorful sails reminds me of a summer in Minnesota where my jerk of a cousin taught me to play Bloody Knuckles after everyone went to bed. Bloody knuckles, now that was a game, and games remind me of the bizarrely different ways human beings have figured out how to communicate, which is the EXACT topic I’m currently writing about, so I jump back to my MacBook and continue writing.

Or perhaps I don’t find my sailboat segue. Perhaps the harbor takes me in a different direction and I’m inspired to switch tasks. Fine, back to that email where I’ve been writing a response to a flame mail from a well-intentioned engineer who has suddenly realized that he’s been ignoring the web for five years. And it turns out the web has changed a bit and his five-year-old mastery of web technologies is now obsolete. His recent discovery of his irrelevance (cough: Fez) has turned into this flame mail, which requires a careful response. And, you know, email is just another bizarre construction by which we communicate AND HEY that’s the topic I was just writing about, so I switch back to my original writing task.

The actual elapsed time that occurred during the previous three paragraphs is about 10 seconds, including my five-second inspirational pace in front of window. And if you were watching me, you’d think, “restless, unfocused, multitasker”. What you can see now, with internal context, is that I’m really only working on one thing: the article about communication.

Yes, I almost made a switch to another task, extinguishing the flame mail, but even if I did, I’d still have the echo of what I was just doing. Tasks get messed up in my head, yes, but mixing shit up is how you build new shit.

Distributed Attention

Back to Gladwell’s research. What they learned was that the five-year-olds were “Attending quite strategically, distributing their attention between toy play and viewing so that they were looking at what for them were the most informative parts of the program. This strategy was so effective that the children could gain no more from increased attention.”

Multitasking is the art of distributing your attention and, guess what, you’ve instinctively known how to do it since you were five. What have you done since then? You’ve worried about information overload, you’ve devised a new way to get things done, and you’ve thought “That’s me!” when someone has taken the time to describe something you already knew.

Me, I’m watching how I context switch. I’m learning when I need to switch to a new task or just relate what I want to do with what I’m currently doing. I’m figuring out the right environment to seed my tasks and my non-tasks that push my ideas towards a coherent structure. At the same time, I’m acknowledging that documented excessive structure might sell books and provide misleading comfort, but it doesn’t provide much space for inspiration.

My Cave, wherever I build it, is a deceptively creative structure. I surround myself with creativity-driving, chaotic-seeming natural order, which is built with the understanding that I can only do one thing at a time, but when I stop, I create.

It’s Windy in Wellington

The presentation season kicked off for me with a week in New Zealand at the Webstock conference. I arrived early, which, as it turns out, wasn’t the best use of my time, as I spent two solid days of what should have been vacation stressing about slides.

Among the many highlights was the speaker dinner held the night before the conference where I met far too many bright people to list here. As I walked back to my hotel room along the waterfront with my head buzzing from the after effects of rapid content acquisition, I heard someone whistling.

No, not someone. Something.

Wellington is at the south end of the North Island, which somehow makes it incredibly windy. The wind varies from a gentle breeze to a hat-removing, lean-into-it, category 4 wind storm. My guess is that residents don’t notice the wind, but I wonder if they notice the whistling lampposts.

I’ve no idea whether this was intentional design or not, but when the wind hits them just right, I swear the cylindrical holes in the lampposts whistle. In unison. I walked by multiple times during my week in Wellington just to see how the lamp posts were singing that particular day because I wasn’t sure if it was a fluke. It wasn’t.

Whether someone intentionally designed these lampposts or it’s a happy coincidence is irrelevant. It’s a great example of one of the unspoken goals of going to any conference: you travel to discover the truly unexpected.

SXSW is Big

It’s big and becoming notorious for the fact that while everyone goes, many skip the panels because the panel structure provides less content and more rambling conversation where there is no guarantee that a rock star set of panelists are going to say anything useful.

Guess what? I can get the same thing with the same rock star panelists and a higher hit rate of usefulness in the unstructured environment of that random bar on 6th street at two in the morning.

My contribution to fixing the SXSW problem is the following. First, John Gruber and I are following the lead of Jim Coudal and Brenden Dawes, by spending an hour delivering content, not conversation. The topic is Blood, Sweat, and Fear: Great Design Hurts and, oddly, I think I’ll lead off with a compelling design story about Mentos. We’ll see how that works out.

Second, I also have the pleasure of moderating a panel titled Designing for Freedom and, as with each year, I have been honored with a rock star set of panelists, which includes:

• Gina Bianchini (CEO of Ning)
• Anil Dash (VP Evangelism at Six Apart)
• Braden Kowitz (User Experience Design Lead at Google)
• Brent Simmons (Creator of NetNewsWire)

As an aside, the panel is up against the keynote with Mark Zuckerberg, but my thought is this: “Think of how much time you’ve already wasted on Facebook, why waste more?”

Yes, it’s a panel and I just ripped panels, but my commitment is this: we’ll stay on topic, say something bright, and we’ll be available for yelling at a local bar shortly after the panel.

Whistling Lampposts?

I knew Webstock was a hit when it was 2am and I was standing outside a bar yelling at some bright someone about some bright thing and having a ball.

Webstock is small. 500 or so, but I’ve never been to a conference where the audience had such a sense of community. Sure, it’s a function of the size of the design population of New Zealand, but that doesn’t explain why Webstock had such personality. I can firmly point my finger at the passion, expertise, and professionalism of the organizers, but I think I should also point at their humility and simple goal of “Let’s build the new, which encourages fertile chaos”.

For me, a conference finishes with a list. It’s a combination of names from business cards and names I simply remember. These aren’t necessarily folks that need an immediate follow-up; it’s the “remember this person” list and how I discover these people and why I need to remember them is a function of the creativity entropy of the event.

I don’t know if this entropy is definable, controllable thing. My guess is SXSW has it and will continue to have it as long as the population believes those bars remain an intellectually target rich environment. As for Webstock, it’s on the other side of the world, but they’ve defined an event you must experience simply because you want to find your own whistling lamppost.

Out Loud

It’s the calm before the presentation storm. Over the next three months, I’ve got four different presentations at Webstock and SXSW. I’m also the best man at a wedding in Washington, all of which means I’m spending most of my down-time thinking up things I’m going to say in the future.

If you’re looking for advice on giving a presentation, the Internet is chock full of endless advice. I’ve been here, too. If you’re looking for tips on writing the presentation, the Internet goes dark — for a fairly simply reason. To think about how to write a presentation, you need to think about how you speak, and that’s not what you’re doing when you read or write. I’ll demonstrate. Say the following out loud right now:

I am reading this out loud to no one in particular.

Were you surprised to hear your voice? I was. Did you actually read it out loud? No? Why not? Sitting in a coffee shop? Worried that the guy next to you will think you’re a freak? This basic discomfort is the reason it’s tricky to explain how to present in an article. The skills involved in writing a clever paragraph are completely different from those used for developing and delivering that clever paragraph to a room full of strangers.

You still haven’t read it out loud, have you?

Presentation or Speech?

Developing a compelling presentation involves a series of decisions and exercises to align your head with the fact that you’re delivering your content directly to people. No internet. No weblog. Just you.

Your first decision: speech or presentation? Wondering about the difference? Take a quick look at these two entirely different appearances by Steve Jobs. The first is his Three Stories speech at Stanford and the second is part of his MacWorld 2007 keynote.

You only need to watch a few minutes of both to get a feel for the difference between a presentation and a speech. My guess is you only viewed the Stanford video because everyone has seen Steve Jobs at MacWorld and the Stanford video is a shocker. Clearly, it’s Steve Jobs. It’s his voice, he’s got his trademark bottle of water, but the delivery is completely anti-Jobs because he’s reading his compelling stories from a piece of a paper.

It freaks me out.

In his autobiography, regarding his stand-up comedy years, Steve Martin writes, “If you don’t dim the lights… the audience won’t laugh.” This subtle, paradoxical observation is the core difference between speeches and presentations. In a presentation, half of the art is figuring out how to create an environment where your audience can actively participate without knowing they are participating. In a speech, the audience may laugh or cry, but they are not required nor encouraged to participate, because, during a speech, the spotlight never leaves the speechmaker.

For a presentation or a speech, you need your audience, otherwise it’s just you in an empty room talking to no one in particular, and we already have a word for that… it’s called writing.

The Unforgivable Mistake

There is one unforgivable mistake when giving a presentation. You’ve heard it before: “Don’t read from your slides.” As you’ll see, my approach for presentation development is designed around avoiding this cardinal mistake, and it starts with picking the right tool.

For all of my presentations during the past three years, I’ve done all my content creation inside of my presentation software, which, thankfully, is Keynote. In the back of my mind, I’ve wondered if this is the right tool to iterate a presentation. Shouldn’t I follow the same process as writing and drop all my thoughts into TextEdit where I can easily slice and dice complex thoughts? No.

Start with and stick with Keynote or whatever presentation software floats your boat. First, presentation software is effectively designed to be outline software and that’s a great tool for organizing and editing your thoughts while not allowing them to become a book. By keeping your presentation in slide format, you’re forcing your content to remain a presentation, not an article. Where each slide is a thought. Where moments of undiscovered brilliance are sitting between bullet points. We’ll talk about how to find this brilliance in a bit, but for now, iterate in the slides.

Your job is to get as much of the meat as possible into outline form so that you can begin to transform it into a presentation. Don’t worry about how you’re going to say something or whether folks are going to get it. If you’re worried that the outline doesn’t allow you to capture the essential detail that you could with a blank piece of paper, start taking notes. I like the stickies in Keynote for random small thoughts. I like the speaker notes for bigger ones.

What’s going to happen as you edit and re-edit is that an initial structure will emerge from your outline. Better yet, since you’ve stuck with presentation software, I’m guessing you’re already starting to hear your voice in your head on certain slides…

• “This is a key point. I need to say this one reeeeeeeeallly slowly because it needs to stick.”
• “Good data that needs to be conveyed, but… dull. Needs hip.”

Once you’ve got what looks like a rough outline of your presentation, it’s time to invoke The Disaster.

The Disaster

This is the second time I’m going to ask you to do something and the second time I just want you to do it. No questions asked. I want you to go to the first slide of your presentation, stand up, and give your presentation.

Wait what whoa Rands this is rough and it’s missing thoughts and uh…

Quiet. Give it a shot. Beginning to end, each slide, I want to hear your presentation.

Done? How’d it go? There’s a reason I call it The Disaster, you know. There are three reasons you should tough out your rough presentation with zero prep:

1. Get a feel for how it fits all together.
2. Hear yourself speaking. This is more reinforcement that you aren’t writing a book, you’re writing a presentation.
3. Build confidence. You now know the absolute worst case scenario regarding this presentation. There is no way it could be worse than what you just went through.

Did you notice as you stood in your office talking to no one in particular how thoughts in your head sounded different than on the slides? Did you discover flaws in logic? Mysterious new gaps in content on the slides you’ve been staring at all morning? That’s progress.

During the Disaster run-through, I take a ton of notes. I do this on a piece of paper next to the computer because, as much as possible, I want to stick with the idea that I’m giving my presentation. If I stop to edit my slides, I lose track of tempo and momentum, or worse, I end up re-writing my presentation rather than giving it. These handwritten notes look like this:

• No clue what slide #2 is trying to say.
• Segue between #4 and #5 is non-existent
• #10: Repeating myself

Your first job after your Disaster is to integrate your notes as quickly as possible. For me, the post-Disaster edit is also the single biggest change I’ll make to the presentation. In addition to major structural changes, I also find new content that needs to be added.

Reduction

This is a good time to remind yourself how to not throw up. This is the topic of an article from last year I wrote on the topic of preparing to give — not develop — your presentation, and there are huge useful intersections between these articles. For those NADD afflictees out there, I present this article in three slightly revised bullet points:

• Practice endlessly (so that you can)
• Improvise (but never stop)
• Fret (ting)

In terms of developing your presentation, I’m going to further modify bullet #1 for this article. It’s now, “Practice and edit endlessly”. This is the largest piece of work where I have the least advice because you need to stare at your slides at 2am for three nights in a row. You need to soak in your presentation. So, mix it up. Invoke another disaster. Pitch a friend. Print your slides and pitch a tree in the woods.

My best piece of advice is a threat: an audience can smell an immature presentation on the very first slide. It has nothing to do with the quality of the content; it’s you standing lamely in front of your slide and silently conveying the “Ok, what I am going to talk about here?” vibe, and it’s presentation death.

During this endless editing and practice, you’re looking for a reduction and consolidation of slides to occur. It’s not that you’re saying less, it’s that you’re beginning to internalize the content so you no longer need all those words to remember your point. It can be disconcerting to delete your fine ideas, so use the speaker notes or stickies if you feel you’re going to forget something important. You aren’t going to need them, but if it makes it emotionally easier to prune, terrific.

This consolidation is one of the reasons I don’t usually send my slides to folks who ask after the presentation. My slides, standing on their own, rarely make sense without me standing in front of the room furiously waving my arms.

Second, as part of your consolidation, you’ll want to start thinking about where you want to use images rather than words. Remember, a presentation is a visual and auditory medium, and a slide covered with words is, well, a cop-out. If you’re only going to use words to describe your fine idea, why don’t you just send everyone an email instead of wasting an hour of their time reading the same thought plastered on the wall behind you.

This presentation is only partially about you and what you think. Yes, you are the guiding force, but the goal is to present an idea with space around it. In this space, your audience is going to pour their own experience and their opinions; they’re going to make your idea their own. Pictures, charts, and graphs create structured, memorable space. I use them in two ways: either to replace an entire thought wholesale or to augment a word slide that needs more space.

A Design Aside: The visual design of your slides is an important topic that is outside the scope of this article, but know this: I’ve seen people lose their minds tweaking animations and transitions on slides. They try every single animation in the hope that just the right transition will add that certain something to their presentation, but what they don’t know is that an animation fixation is usually a sign that your content blows. The same rule for typefaces applies for transitions and animations. The less your audience sees your design decisions, the more impact they’ll have.

Third, you’re looking for an underlying structure to your presentation that you’re going to want to share with your audience. During all of this endless practice, you’re going to develop a feel for how your presentation fits together, but this structure may not be initially obvious to your audience. For any reasonable-sized presentation, you need to design a visual system that allows audience members to instantly know where they are.

Fourth, and lastly, you’re looking for audience participation opportunities in the flow and tempo of your presentation. Where are you going to turn the lights up a little bit and remind the audience that they’re sitting there, soaking in your thoughts? Let’s talk a bit more about this.

Presentation Punctuation

Participation is presentation punctuation. You’re going to use participation to accentuate parts of your presentation. You’re going to use it to break up complex thoughts into digestible, comfortable ideas. But you only have partial control of when folks will actually participate.

The most common participation technique is the show of hands opener. It’s usually done at the beginning of the presentation as a warm-up:

• “Show of hands — how many of you own a Mac?”
• “Quickly, how many of you think you’re paying too much for term life insurance?”

As a warm-up technique, I’m a fan of the opener. It’s an up-front reminder that this is not a speech, it’s just an opening salvo and you’ve got another hour to fill. As you’re endlessly practicing your slides, look for sections that are idea-heavy and give your audience a shot in the arm with a question. You don’t even have to ask for a show of hands, just direct the spotlight at them for a moment.

Tell me exactly what you do with your fingers when you read at your computer.

You’re only going to be able to plan so much of your audience’s participation, and therein lies the beauty of actually giving a presentation: you don’t know when your audience is going to show up. Dull, wordy slides I considered deleting often got the biggest laugh. Visual slides that I’ve poured my heart into are often complete duds. You won’t know until you’re there.

Something for their Pocket

What do you want your audience to remember? I should’ve asked this at the beginning, but I’m asking it now because you’re almost done with your presentation and I want to know what your giving your audience that fits in their pocket. I want to know what part of your presentation is actually going to leave with them.

There’s a really easy and cheap way to do this and it’s the Lessons Learned slide. It’s the bulleted list of important points slide that, when displayed, invariably results in a slew of cameras and iPhones appearing in the audience because they know this slide fits in their pockets.

Regardless of whether or not you use it, the Lessons Learned slide is a handy one to have at the end of your deck during the entire presentation development. It defines the basic structure of your presentation and represents a goal. Could you give your entire presentation from a single slide. 50 minutes, a room full of people, and you with your single slide with six bullet points?

That’s your goal, and you can have a wildly successful presentation without achieving it, but a one-slide presentation represents the ultimate commitment to your audience. It says, “This isn’t about slides. This about me telling you a great story… out loud.”

Pixel Rigs

I have an unnatural fixation with pixels.

For two years I was a stalwart supporter of the 17-inch PowerBook/MacBook Pro. My argument was simple and ignorant: “You need as many pixels as possible because you need to be able to see as much as possible.”

This pixel fundamentalism blinded me to the simple fact that the 17-inch was just too big and heavy. Yes, 17 inches is bigger than 15 inches, but the primary use case for a portable computer is mobility, and lugging around a 6.8 pound gorgeous piece of aluminum is a total mobility buzz kill. A creative tool should never be an anchor.

Yes, when I finally switched to a 15-inch, I was instantly happier. The weight and size elegantly integrated better with my travel habits and I didn’t miss the lack of roughly half a million pixels for a moment.

Besides, NOW WE’VE GOT SPACES AND UNLIMITED PIXELS WOOOOOOOOO! Ok, no, Spaces isn’t the right pixel solution, but that’s a different article.

Now, my desktop computing solutions don’t have the mobility requirement, which means, as frequent readers know, I continue to lose my pixel mind when it comes to screen real estate. What started as a treatise to justify the necessity of 30-inch flat panels has slowly twisted and turned into a seemingly insatiable need for more pixels.

Seriously. One of my current background drive-to-work soak projects is a justification for a second 23” flat panel turned on its side… and you can help.

I’ve created a Flickr group called Pixel Rigs where I’m dying to see your pixel rig. Go grab your favorite camera, take a shot of your desktop, and post it to Flickr. Unlike prior excursions, stage your desktop a bit. Let us see how you’re managing pixels. Go crazy with Flickr’s notes features… like this:

Windows, Mac, Linux, whatever… explain to everyone how you’ve tamed your personal pixel fixation.

Year in Twitter

I’m a sucker for charts’n’graphs.

The only thing better than data is data about data. Data about data is information that, in quantity, becomes knowledge, which is just a short hop away from wisdom. And when wisdom shows up, you know you’re this close to figuring it all out.

As a nerd who erroneously believes that the world is a knowable system, charts’n’graphs further the illusion that I’m one epiphany away from this complete knowledge.

Twitter’s deliberately spartan feature set has no charts’n’graphs. In fact, most of the information you can learn about your personal Twittersphere is summed up on the front page: following, followers, favorites, direct messages, and updates. That’s it.

Twitter has become a daily social touch point for me. In fact, I’ve started to see the @reply_to_someone convention outside of Twitter particularly in email:

“Did anyone take notes at the design meeting? I saw @markjz and @wenderz scribbling something.”

Given the amount of social energy I’m pouring into Twitter, I’ve been wondering how I’ve been using it. Fortunately, @dacort has written a fine Perl script to suck down all your twits, chew on them a bit, and spit them out into delicious charts’n’graphs in Numbers.

Staring at this year in review for Twitter has given me the following information:

• The @replies aren’t really a surprise, as these are folks I work with or who are avid Twitter buddies. I suspect the interesting data here is in the long tail. How many folks have at least one @reply?
• I’ve been stewing over the lunchtime Twitterspike for a couple of days. In an early version of the stats, there was a spike around 2pm and that spike is still there around Noon in the latest stats. Before seeing either of these graphs, my guess would’ve been that I was chattier in the morning. Looks like I’m apt to fire off a Twitter right after lunch to set the tone for the afternoon.
• The Twitters per month really tell the story of my year: “Getting to know Twitter during the first half of the year, and then August arrives and I’m totally fucking buried with work, which is followed by a couple of months of not wanting to see a computer ever again. December shows up and I’ve got time off, so WHAM… Twitters galore.”

Sadly, the most interesting information isn’t included in these charts’n’graphs and that’s influence. How many people am I following and how many do they follow? How many folks have been following me? Who do I know that they know? It’s the intersections of my Twitter network that I really care about because that is how I can figure out how efficiently collecting and distributing the really juicy information.

Happy New Year.

A Brief Glimpse

Just back from Scotland for recruiting. Same universities as last time, St. Andrews and Edinburgh. Last year, this is the trip that inspired the A Glimpse and a Hook article, so it’s appropriate that this year’s trip forces a revision.

I bagged on the objective section of the resume in the Glimpse piece, using the argument that I found objectives pointless, but after a solid week of scrubbing, thinking, and talking about resumes, I’m prepared to get proactive. Sure, many objectives are crap. The question is, why are they crap?

A crappy objective section in a resume suffers from the same issues as the rest of the resume: standardization. Your first resume started with a question: “How do I write it?” A kind person whipped out a resume, showed it you, and it resonated with you so you copied the structure. Problem was, you didn’t stop there. You also copied the style of the writing. You borrowed the boring, vanilla language where you described your hopes and dreams in the language of business. “I am a motivated team player looking for a high growth opportunity at a company which does not blow.”

Yuck. The only interesting word in that objective is blow.

I’m a fan of grabbing the bright ideas of other people, but I’m a bigger fan of you tweaking their ideas and making them your own. Your resume, like your objective, should give me a sense of you and where you’re going. I want to see a little ego and I want to see your character because I’m not hiring a flat piece of paper, I’m hiring a person. But when I start, all I have is the paper.

Professionally Pointed

I update my resume every six months whether I’m looking for a new gig or not.

A resume refresh gives me perspective. I don’t get a report card much anymore, just a yearly focal review which pretty much tells me what I already know: grew a little here, fucked up there… a bit more money.

A resume revision doesn’t remind me of how I’m doing, it forces me to think about where I’m going. Your objective, like your resume, is a snapshot of your professional life. In a few brief sentences, you need to clearly describe your professional goals in your own voice. You need to explain where you are professionally pointed.

Here’s my current objective:

I need to work with bright people who don’t take no for an answer and are crazy about well-designed software. If these people aren’t there when I show up, I work hard to find them.

Is this everything I’ve ever wanted to achieve? No. Will the reader understand all of my skills, all of my capabilities? No. Will they get the idea that I value design, people, and might be a little crazy? Yup.

When you’re thinking of your objective, I want to think of yourself sitting at bar. You’re two drinks in and you’re pitching a friend about what you want to do with your life. While this casual, egotistical, mildly trashed tone may best suit high tech gigs, seriously, what do you have to lose being yourself?

Resume Stress

You’re stressing as you work on your resume because usually when you’re updating your resume, you’re in need of a job. In this stress, you fall back on convention — on standardization — because getting the resume done feels less important than the job hunting and being original takes a lot of work.

Problem. There are a bazillion people out there who are looking for the same gigs you want. The barrier to entry is not that someone can hunt down a job opening; the barrier to entry is getting noticed amongst a sea of mediocre resumes.

Here is an audacious goal for your resume: to get you to a point in your career where you no longer need a resume. It’s the point that in your chosen industry people know who you are and what you are capable of. And they want you doing it at their companies.

It’s a tricky lifetime goal, one that I’m still working on, but that’s the goal I want you to think about when you’re stressing about your professional objective. It’s not your next job you need to stress about; it’s your career.

The Nerd Handbook

A nerd needs a project because a nerd builds stuff. All the time. Those lulls in the conversation over dinner? That’s the nerd working on his project in his head.

It’s unlikely that this project is a nerd’s day job because his opinion regarding his job is, “Been there, done that”. We’ll explore the consequences of this seemingly short attention span in a bit, but for now this project is the other big thing your nerd is building and I’ve no idea what is, but you should.

At some point, you, the nerd’s companion, were the project. You were showered with the fire hose of attention because you were the bright and shiny new development in your nerd’s life. There is also a chance that you’re lucky and you are currently your nerd’s project. Congrats. Don’t get too comfortable because he’ll move on, and, when that happens, you’ll be wondering what happened to all the attention. This handbook might help.

Regarding gender: for this piece, my prototypical nerd is a he as a convenience. There are plenty of she nerds out there for which these observations equally apply.

Understand your nerd’s relation to the computer. It’s clichéd, but a nerd is defined by his computer, and you need to understand why.

First, a majority of the folks on the planet either have no idea how a computer works or they look at it and think “it’s magic”. Nerds know how a computer works. They intimately know how a computer works. When you ask a nerd, “When I click this, it takes awhile for the thing to show up. Do you know what’s wrong?” they know what’s wrong. A nerd has a mental model of the hardware and the software in his head. While the rest of the world sees magic, your nerd knows how the magic works, he knows the magic is a long series of ones and zeros moving across your screen with impressive speed, and he knows how to make those bits move faster.

The nerd has based his career, maybe his life, on the computer, and as we’ll see, this intimate relationship has altered his view of the world. He sees the world as a system which, given enough time and effort, is completely knowable. This is a fragile illusion that your nerd has adopted, but it’s a pleasant one that gets your nerd through the day. When the illusion is broken, you are going to discover that…

Your nerd has control issues. Your nerd lives in a monospaced typeface world. Whereas everyone else is traipsing around picking dazzling fonts to describe their world, your nerd has carefully selected a monospace typeface, which he avidly uses to manipulate the world deftly via a command line interface while the rest fumble around with a mouse.

The reason for this typeface selection is, of course, practicality. Monospace typefaces have a knowable width. Ten letters on one line are same width as ten other letters, which puts the world into a pleasant grid construction where X and Y mean something.

These control issues mean your nerd is sensitive to drastic changes in his environment. Think travel. Think job changes. These types of system-redefining events force your nerd to recognize that the world is not always or entirely a knowable place, and until he reconstructs this illusion, he’s going to be frustrated and he’s going to act erratically. I develop an incredibly short fuse during system-redefining events and I’m much more likely to lose it over something trivial and stupid. This is one of the reasons that…

Your nerd has built himself a cave. I’ve written about The Cave elsewhere, but here are the basics. The Cave is designed to allow your nerd to do his favorite thing, which is working on the project. If you want to understand your nerd, stare long and hard at his Cave. How does he have it arranged? When does he tend to go there? How long does he stay?

Each object in the Cave has a particular place and purpose. Even the clutter is well designed. Don’t believe me? Grab that seemingly discarded Mac Mini which has been sitting on the floor for two months and hide it. You’ll have 10 minutes before he’ll come stomping out of the Cave — “Where’s the Mac?”

The Cave is also frustrating you because your impression is that it’s your nerd’s way of checking out, and you are, unfortunately, completely correct. A correctly designed Cave removes your nerd from the physical world and plants him firmly in a virtual one complete with all the toys he needs. Because…

Your nerd loves toys and puzzles. The joy your nerd finds in his project is one of problem solving and discovery. As each part of the project is completed, your nerd receives an adrenaline rush that we’re going to call The High. Every profession has this — the moment when you’ve moved significantly closer to done. In many jobs, it’s easy to discern when progress is being made: “Look, now we have a door”. But in nerds’ bit-based work, progress is measured mentally and invisibly in code, algorithms, efficiency, and small mental victories that don’t exist in a world of atoms.

There are other ways your nerd can create The High and he does it all the time. It’s another juicy cliché to say that nerds love video games, but that’s not what they love. A video game is just one more system where your nerd’s job is to figure out the rules that define it, which will enable him to beat it. Yeah, we love to stare at games with a bazillion polygons, but we get the same high out of playing Bejeweled, getting our Night Elf to Level 70, or endlessly tinkering with a Rubik’s Cube. This fits nicely with the fact that…

Nerds are fucking funny. Your nerd spent a lot of his younger life being an outcast because of his strange affinity with the computer. This created a basic bitterness in his psyche that is the foundation for his humor. Now, combine this basic distrust of everything with your nerd’s other natural talents and you’ll realize that he sees humor is another game.

Humor is an intellectual puzzle, “How can this particular set of esoteric trivia be constructed to maximize hilarity as quickly as possible?” Your nerd listens hard to recognize humor potential and when he hears it, he furiously scours his mind to find relevant content from his experience so he can get the funny out as quickly as possible.

This quick wit is only augmented by the fact that…

Your nerd has an amazing appetite for information. Many years ago, I dubbed this behavior NADD, and you should read the article to learn more and to understand what mental muscles your nerd has developed.

How does a nerd watch TV? Probably one of two ways. First, there’s watching TV with you where the two of you sit and watch one show. Then there’s how he watches by himself when he watches three shows at once. It looks insane. You walk into the room and you’re watching your nerd jump between channels every five minutes.

“How can you keep track of anything?”

He keeps track of everything. See, he’s already seen all three of these movies… multiple times. He knows the compelling parts of the arcs and is mentally editing his own versions while watching all three. The basic mental move here is the context switch, and your nerd is the king of the context switch.

The ability to instantly context switch also comes from a life on the computer. Your nerd’s mental information model for the world is one contained within well-bounded tidy windows where the most important tool is one that allows your nerd to move swiftly from one window to the next. It’s irrelevant that there may be no relationship between these windows. Your nerd is used to making huge contextual leaps where he’s talking to a friend in one window, worrying about his 401k in another, and reading about World War II in yet another.

You might suspect that given a world where context is constantly shifting, your nerd can’t focus, and you’d be partially correct. All that multi-tasking isn’t efficient. Your nerd knows very little about a lot. For many topics, his knowledge is an inch deep and four miles wide. He’s comfortable with this fact because he knows that deep knowledge about any topic is a clever keystroke away. See…

Your nerd has built an annoyingly efficient relevancy engine in his head. It’s the end of the day and you and your nerd are hanging out on the couch. The TV is off. There isn’t a computer anywhere nearby and you’re giving your nerd the daily debrief. “Spent an hour at the post office trying to ship that package to your mom, and then I went down to that bistro — you know — the one next the flower shop, and it’s closed. Can you believe that?”

And your nerd says, “Cool”.

Cool? What’s cool? The business closing? The package? How is any of it cool? None of it’s cool. Actually, all of it might be cool, but your nerd doesn’t believe any of what you’re saying is relevant. This is what he heard, “Spent an hour at the post office blah blah blah…”

You can be rightfully pissed off by this behavior — it’s simply rude — but seriously, I’m trying to help here. Your nerd’s insatiable quest for information and The High has tweaked his brain in an interesting way. For any given piece of incoming information, your nerd is making a lightning fast assessment: relevant or not relevant? Relevance means that the incoming information fits into the system of things your nerd currently cares about. Expect active involvement from your nerd when you trip the relevance flag. If you trip the irrelevance flag, look for verbal punctuation announcing his judgment of irrelevance. It’s the word your nerd says when he’s not listening and it’s always the same. My word is “Cool”, and when you hear “Cool”, I’m not listening.

Information that your nerd is exposed to when the irrelevance flag is waving is forgotten almost immediately. I mean it. Next time you hear “Cool”, I want you to ask, “What’d I just say?” That awkward grin on your nerd’s face is the first step in getting him to acknowledge that he’s the problem in this particular conversation. This behavior is one of the reasons that…

Your nerd might come off as not liking people. Small talk. Those first awkward five minutes when two people are forced to interact. Small talk is the bane of the nerd’s existence because small talk is a combination of aspects of the world that your nerd hates. When your nerd is staring at a stranger, all he’s thinking is, “I have no system for understanding this messy person in front of me”. This is where the shy comes from. This is why nerds hate presenting to crowds.

The skills to interact with other people are there. They just lack a well-defined system.

Advanced Nerd Tweakage

If you’re still reading, then I’m thinking that your nerd is worth keeping. Even though he’s apt to vanish for hours, has a strange sense of humor, doesn’t like you touching his stuff, and often doesn’t listen when you’re talking directly at him, he’s a keeper. Go figure.

My advice:

Map the things he’s bad at to the things he loves. You love to travel, but your nerd would prefer to hide in his cave for hours on end chasing The High. You need to convince him of two things. First, you need to convince him that you’re going to do your best to recreate his cave in his new surrounding. You’re going to create a quiet, dark place here he can orient himself and figure out which way the water flushes down the toilet. Traveling internationally? Carve out three days somewhere quiet at the beginning of the trip. Traveling across the US? How about letting him chill on the bed for a half-day before you drag him out to see the Golden Gate Bridge?

Second, and more importantly, you need to remind him about his insatiable appetite for information. You need to appeal to his deep love of discovering new content and help him understand that there may be no greater content fire hose than waking up in a hotel overlooking the Grand Canal in Venice where you don’t speak a word of Italian.

Make it a project. You might’ve noticed your nerd’s strange relation to food. Does he eat fast? Like really fast? You should know what’s going on here. Food is thrown into the irrelevant bucket because it’s getting in the way of the content. Exercise, too. Thing is, you want your nerd to eat healthily so that he’s here in another thirty years, so how do you change this behavior? You make diet and exercise the project.

For me, exercise became the project ten years ago after a horrible break-up. When the project was no longer the Ex, I dove into exercise every single day of the week. There were charts tracking my workouts, there were graphs tracking my weight, and there was the exercise. Every single day for two years until the day I passed out in a McDonald’s post-workout after not eating for a day. Ok, so time for a new project. Yeah, nerds also have moderation issues. That’s another essay.

Significant nerd behavioral change is only going to happen if your nerd engages in the project heart and soul, otherwise it’s just another thought for the irrelevant bucket.

People are the most interesting content out there. If you’ve got a seriously shy nerd on your hands, try this: ask him how many folks are in his buddy list? How many friends does he have in Facebook? How many folks are following him on Twitter? LiveJournal? My guess is that, collectively, your nerd interacts with ten times more people than you think he does. He can do this because the interaction is via a system he understands — the computer.

Your nerd knows that people are interesting. Just because he can’t look your best friend straight in the eye doesn’t mean he doesn’t want to know what makes her tick, but you need to be the social buffer — the translation layer. You need to find one common thread of interest between your nerd and your friend and then he’ll engage because he will have found relevance.

The Next High

As you discovered when you were the project, your nerd’s focus can be deliciously overwhelming, but it will stop. Once a nerd believe he fully knows how a system works, the challenge to understand ceases to exist and he moves on in search of The Next High.

While I don’t know who you are or why in the world you chose a nerd for your companion, I do know that you are not a knowable system. I know that you are messy, just like your nerd. Being your own quirky self will be more than enough to present new and interesting challenges to your nerd.

Besides, it’s just as much a nerd’s job to figure you out and maybe someone somewhere is writing an article about your particular quirks. Good news, he’s probably reading it right now.

The Gel Dilemma

Two years ago, I figured out my favorite pen was no longer being produced in its current form. A quick scan of my local office supply stores revealed nothing. This fact, along with the total lack of auctions on eBay featuring my now discontinued pen showed me that a) I was screwed, and b) I’d become fond of an unremarkable pen.

I avoided a total pen breakdown for a few months simply by looking for this pen in my home and work environments, as I was sure I’d find remnants of the six boxes of pens that had mysteriously liberated themselves from my office over the past four years. In a week, I’d built a small stockpile of reclaimed, partially used pens, but it is a fundamental law of office supplies that a pen wants to be free. Despite my best efforts, my stockpile was slowly depleted.

The crisis arrived in the last month when a rush purchase at Office Depot resulted in a jar full of pens that demonstrated some of the worst writing utensil characteristics: cheap feel and erratic ink flow. Each time I picked this pen up I felt, “Everything I’m about to write is going to look like crap.”

It’s time for an educated change.

The Joy Vectors

Each time I pick up and use a pen, I want to feel a bit of joy. These joy vectors are:

• The way the pen sits in my hand. I should feel I have a firm grip.
• The way the pen applies ink to the paper. I like a thick, consistently black line on the paper. This is both a function of the ink and the construction of the tip.
• The fact that I know the pen is readily available. I want to be able to find the pen in a nearby office supply store. I don’t want to end up high, dry, and penless any time in the near future. Yes, I think about this each time I pick up a pen.

I also have existing baggage regarding pens.

First, my assumption is that the more moving parts in a pen, the less precision I have when the pen tip touches the paper. I have not deconstructed a retractable pen, but my gut tells me I lose energy among the pen casing, the retracting mechanism, and the tip. This is one reason that I am biased against pens that click. The other reason is… they click. Over the past few weeks of my pen evaluations, I’ve noticed that when most people pick up a retractable pen, they click it, roughly five times. Not joking.

Second, and related to the moving parts issue, I’m not a fan of the cushioned grip pens. The cushioned grip reminds me of third grade when Ms. Ockerman handed out these humongous, triangular, watermelon-scented grips for our pencils. They made me feel clumsy then and they make my pens feel squishy now. People. I have finger strength. Really.

Lastly, and most important, I only use gel-based pens. I don’t know when I made the transition, but I can tell you when I’m not using one because I immediately throw it away — I despise how non-gel-based ink plays on the paper. But I don’t know why. Turns out it’s the gel. Go figure. According to Wikipedia, “What distinguishes a gel pen from a ballpoint pen is the gel ink which consists of pigment suspended in a water-based gel.” They go on to describe, “… how gel inks resist common laboratory analysis.” I’ll translate both facts: if you’re using gel-based pens, you’re going to get deep, rich lines which can not be traced by covert agencies. Bonus!

Interface Points

Using the joy vectors as a structure, I returned to Office Depot and purchased six pens all in roughly the same price range. With each of these pens, I conducted three tests:

• The Glamour Test. How does it look? How does the pen feel in my hand, and, more importantly, can I spin it around my thumb?
• The Line Test. How does the ink flow? The basic straight line.
• The Writing Test. This test brings it all together. How does my writing look? Is the pen helping or hurting?

The Glamour Test

You can scroll to the bottom if you’d like to see the names of the six pens I ended up selecting, but you’ll have more fun waiting. The results of the Glamor Test were:

#	Type	Size	Tip	Casing and Grip	Weight	Spin
1	Retractable	.7	Plastic	Comfortable — not too big — boring cushioned grip	Very light	Hard to spin
2	Retractable	.7	Metal	Cheap plastic casing — large and clumsy	Heavy	Very spinnable
3	Capped	.8	Metal	Cheap casing and grip	Weight is right	Spins well
4	Retractable	.37	Metal	Solid feel — shortest of the six which leads to odd balance	Weight is right	Shockingly, very spinnable
5	Capped	.5	Metal	Perfect feel even with the leathery grip	Weight is perfect	Serious spinnage
6	Capped	.5	Plastic	Wide feel, slick casing. Meh.	No issues here	I can spin this pen

The Line Test

For our next test, I drew a straight line using a ruler. This brings up the sensitive issue of what paper to use. I’m going to avoid this entire debate and just use a Moleskine simply because if you’re going to have an argument about pens with anyone, chances are there’s a Moleskine nearby.

Photos of this size really don’t tell you much, so, for the next two tests, I recommend looking at the larger size. My methodology in this shot was simple: plant the pen on one end of the paper, grab the ruler, and then draw a straight line across the paper. You’ll notice an unexpected piece of data in that during the time I fumbled with ruler placement, you can see how the paper soaked in the ink. You’d think this was a function of the nib, or tip, size, but you can clearly see that #2 with a .7mm nib soaked in much quicker than the larger #3. Wonder what is going on there.

The line test shot doesn’t tell much unless you’re doing the lines yourself, but:

• The small nib size of .4mm (called “micro”) was intensely annoying. Even though this pen had the firmest feel of the retractables, gel ink being used for fine lines feels like heresy. This pen is eliminated.
• As much as possible, I tried to use the same amount of pressure drawing each line, but, as you can see, pens with the same nib size can draw with varying line thickness.

The Writing Test

All of this pen fretting leads to the final test: how does it write? How does it perform when the last thing you want to do is think about the pen rather than what you’re writing? Here’s how they look:

As with the line test, examining a much larger shot may prove more interesting. My observations and eliminations:

• Following the elimination of #4 for thin lines, I’m eliminating #3 for fat lines, which are also a function of the huge casing.
• While the quality of lines among #1, #2, #5, and #6 is comparable, I’m eliminating #2 and #6 because of the girth of the pen. The casing is huge and feels awkward in my hand, which results in strange penmanship.
• Comparing the last two pens, #1 and # 5, it’s clear that #5 is the winner, but here’s the catch, #5 is my loser pen – my previous favorite that’s not available in its current form. This makes #1 the winner by default.

The Wrap Up

The pens in this competition were:

#	Name	Type	Size	Result
1	Pilot G-2	Retractable	.7	Winner!
2	PenTel Energel	Retractable	.7	Eliminated — Unwieldy size and cheap casing
3	Pentel Hybrid Gel Roller	Capped	.8	Eliminated — my current replacement and it’s crap
4	Uni-ball Signo	Retractable	.37	Eliminated — lines are too thin
5	Pentel Hybrid Gel Grip	Capped	.5	Eliminated — no longer readily available. I love this pen
6	Pilot V-Ball Grip	Capped	.5	Eliminated — Casing is too big

Unfortunately, I’m not sold on the winner. After my contest was over, I began to use the G-2 as my go-to pen. While the flow is fine and the feel is good, I’m still not over my precision-loss-to-the-retractable-mechanism paranoia. Fortunately, actively worrying about pens for a few weeks will introduce you to an entire pen sub-culture. After asking friends about their favorite pens, I was sent off to a local Japanese paper store where there was an entire wall of gel pens sporting strange names and being sold in individual plastic wrappers. Visions of a secondary competition starting bouncing around my head.

For now, I’m editing this article in front of the fireplace using a capped G-3. It’s a little wider than I’m used to, but I swear the lack of moving parts is keeping my already messy penmanship in check. Tomorrow, I’m going to give a different Uni-ball Signo a whirl. This badass capped pen is almost an exact replica of my beloved PenTel, including the total absence of a plastic grip.

All of these exotic new pens are a violation of my readily available joy vector, but, you know, I’m prepared to be fond of a remarkable pen.

The Twitter Equilibrium

I’m back from a few days in Vegas. Before I left, I decided it was time to talk a bit more about Vegas, and I decided I’d Twitter tips for what I consider to be a successful Vegas trip. Thing is, from the moment I set foot in the airport, I realized I had a million tips to send, but I also knew that I had to sensibly and carefully dole them out. I needed to maintain a Twitter equilibrium.

Yeah, that’s a mouthful. I’ll explain this in a moment.

Before the definition, you need understanding how I’m using Twitter. For me, Twitter is a desktop application like Twitterific. It’s not a bookmark and it’s not a webpage; it’s an integral part of my real-time desktop alongside Mail, iCal, iChat, Stickies, and Safari. I use the Twitter website, but I use it as an administration tool to manage my account. I rarely use it to actually read Twitters.

Second, you need to understand my mental model of Twitter. In my head, it’s a chat room. When I sit down at my computer, I expect there to be a reasonable amount of new content from bright people. In my head, I have no idea that these people can’t actually hear each other’s Twitters. You’d think that’d present a conversation consistency problem, but it doesn’t because I don’t let the chatter get out of control —- I maintain a Twitter equilibrium.

This equilibrium is the state when Twitter is providing you with precisely the right frequency and quality of content that you expect. It’s totally arbitrary and completely personal while also being essential to preventing Twitter from becoming another useless, annoying social networking tool that you maintain out of a weak sense of loyalty to people you don’t actually know.

For me, I’ve achieved a Twitter equilibrium following roughly 100 people. For whatever reason, at around 100 folks, I’m finding a pleasant flow of new, interesting content whenever I glance over at Twitterrific. I’ve been refining this number since I started using Twitter and, during that time, I’ve found a couple of essential information management rules:

Rule #1: Remove noisy people. Even if you love them. Probably the easiest way to get turned off Twitter is following someone who is filling Twitter with useless noise. This is especially common with newcomers who are still figuring out that Twitter is the king of casual information, so I cut new people some slack. If the problem persists, they’re out. Good friends who I talk with daily get noisy and get removed, too, but, yeah, I eventually end up following them again.

Rule #2: Follow Rands’ First Law of Information Management. Which reads: “For each new piece of information you track, there is an equally old and useless piece of information you must throw away.” If you continue to follow new people, eventually they’re going to overwhelm you with their casual information flood, so you must get in the habit of removing a person for each new person that you follow. Incidentally, the first law tastes great with RSS feeds as well.

Those of us afflicted with NADD have a problem with this law, since folks with NADD believe that, at any point, something interesting might happen anywhere. The first law is a compromise — yes, you might throw something away that you could use — but think of it like this: by throwing away crap, you have more time to find new gems.

Rule #3: Find ways to stumble about. While Twitter is a fine way to follow folks you know, there are more people that you don’t know and there’s a good chance they might have something to say. The folks at Twitter recently introduced the Twitter Blocks feature to allow you to do just this, but there’s an easier way to explore your Twitter-hood. Once or twice a week, I glance at the replies page to see messages from folks who are following me, but I might not be following. The choice to engage in a conversation, to me, seems like the single best way to see if we have mutual interests.

100 people doesn’t seem like a lot. I’d like to follow more, but to do that, Twitter needs to step up. Allow me to easily find and prune people who haven’t updated in forever. Let me group or tag people I follow, so I can filter conversations to co-workers, new people, and folks on Twitter probation. I know, I said keep it Spartan, but Twitter’s success will be defined by it’s growth and that means they need to figure how I can spend less time following more people.

Apple Los Gatos x 2

Coffee approach pattern Delta was in play today. This unlisted approach pattern is a stop in Los Gatos to hit one of two decent coffee shops, The Great Bear or the Los Gatos Coffee Roasting company. Neither shop can compete with Peet, but Los Gatos has other attractions. Namely, the soon-to-be-completed Apple Store:

Store errata:

• That big white Apple is a sticker and it’s either in high demand or easy to remove as the store has been through several since the logo appeared in early May.
• Note the rectangular hole in the center of the build which is the future home of the glowing Apple logo.
• Also note the construction has now moved over the sidewalk.
• Local press has been covering the build out of the store which noted that 30’ high glass and stainless steel façade might not fit in the designated historic district. They also suggest a September opening.

[9/1/07 Update]: That was quick…

Coffee and Design

Mornings are a delicate proposition, but there are two events which, if they occur, guarantee a positive experience.  The first event is coffee acquisition. Currently, there are three different coffee approaches, each has its own consequences. They are:

1. Crappy mountain swill.  This is coffee from the local store. They try, but it’s a serious B. Even the cup is limp.
2. Corporate swill. Coffee from work. Again, they try, but they lose quality to volume.
3. Peet’s Coffee. This is the shit. You can’t beat Peet’s. There’s nothing like driving to work with a thin sheen of caffeine induced sweat all over your body.

In terms of setting the mood for the morning, acquisition policy A and B are sufficient, but lack complexity and inspiration. Yes, I get my coffee high, but I’m cheating because it’s a path of least resistance approach: mountain and corporate swill are on the way or at work whereas Peet’s involves a ten minute detour. Committing to this detour leads to a stellar cup of coffee. 

(Note: There is another coffee acquisition tact and that is “Brew your own”. It’s always an A+, but is a time consuming process reserved for weekend mornings.)

The other morning defining event is email. When I first sit down at the computer and load the morning email, I’m, again, looking for complexity and inspiration. Who on the planet took time to send me a great email? Something I can dig my teeth into and leverage my complex coffee high for an equally inspirational response? This morning the mail read, “What are the pros and cons of having design report into engineering vs. product management?”

Wow. Now that’s a question. That’s an “I should write an article about that” question. The extremely short answer is “Geography matters”. Having design and engineering in the same part of the organizational chart means they teach each other all sorts of stuff, make better decisions, and move faster. There are many cons, but I believe the pros vastly outweigh these cons primarily because of the organizational velocity they create.

On Design

I’m going to be talking a lot more about design of the coming months. This starts next month at the Webmaster Jam in Dallas where I’ll be speak on Managing Web Design which is a presentation in dire need of a new title, but you get the idea. Early next year, I’m headed to New Zealand to speak at the soon-to-be-launched Webstock conference. Ideas for this event are still swirling in my head, but design will be on the menu.

Next up is the South by Southwest Interactive festival for 2008.  I’ve moderated panels at the event the past two years and it remains my favorite conference simply because it attracts of set of people you will see no where else. As I mentioned in my post-game report for SXSW2007, there was much discussion that the panels were adrift this year. There are lots of theories as to why this was the case, but that’s water under the bridge and simply a problem to solve.  

I’ve got a one-two punch solution to SXSW panels this year. The first punch is a two-person presentation which I’m proposing to do alongside John Gruber. Titled Blood, Sweat, and Fear: Great Design Hurts, we’ll be tackling the idea that you’re never going to design something great without pissing someone off, yelling at people you respect, and losing sleep thinking that you’re doing the wrong thing. Piqued your interest? Great, mosey down to the much improved panel picker and say so.

The second punch is more traditional panel I’ve cooked up with co-conspirator, Gina Bianchini.  The panel is entitled Designing for Freedom and will explore the idea of how products can be designed so that people can create and make something their own. The quality of a panel is defined by the panelists and I’d love to tell you who we’ve picked for this, but first you need to head back to the panel picker and weigh in.

Speaking and Design

The intent with both of the SXSW2008 panels as well as the other speaking engagements is the beginning of a intentional theme I’m setting for the next year. I want to talk with as many bright people as possible about the intersection of design and engineering. Like management, engineers are not necessarily trained in this discipline, yet they are often asked to make important decisions that affect design. In my ongoing quest to make sure engineers wear as many hats as possible, the next year is going to be chock full of design ramblings, meaty morning emails, and stellar cups of coffee.

Yard Sale

In the past two weeks, I’ve seen a second flood of friend requests on Twitter. Included in this second wave were several Twitter haters who apparently believe that they’ve made their point and now it’s ok to join Twitter.

Welcome.

I wasn’t the first person to jump on the Twitter bandwagon. In fact, my original plan back in February was to give it a two-week trial to see what was what, and it’s now July and I think I’ve finally figured out the what.

Casual Information

I’ve identified two specific and unique uses for Twitter, and this why an application like Twitterific has now become a part of a very short list of must-have applications that I fire up whenever I sit down at a computer.

First, a definition. Twitter and the many Twitter clones are the kings of casual information. This is information that is non-essential, meaning that if this information was never discovered by anyone — no big deal. More on this in a moment.

The reason Twitter owns casual information is based entirely on the spartan feature set they’ve chosen to provide to their users. You can add friends, but the total lack of presence information about the people in your network means you’ve no clue whether or not they’re actually going to read a thing that you type, so you filter yourself. You can’t depend on the information getting to anyone, so you don’t send essential information.

Twitter detractors see this as the biggest nuisance with the service. They claim the casual information relayed via Twitter is non-essential, egotistical, and dull. Oddly, they claim this on their very own weblogs which I find… interesting. What I find more interesting is that you never know when casual information might become essential.

Twitter is an informational yard sale. You simply never know when that off-the-cuff comment you toss will alter a person’s day. I’ll explain via my two favorite use cases:

Use case number one for Twitter is when lots of Twitterees are congregating in the same place. My most recent example of this was at WWDC where my average twits per hour went through the roof. Anyone at the conference with a Twitter account was doing the same thing and it was a brilliant way to sniff around the social undercurrents of the conference. It was also handy for ad-hoc event coordination. The best example of this was a message I sent the last day of conference which read, “Drinks @ the W — 4pm. I’m buying”.

Three hours, thirteen attendees, and several hundred dollars later, I knew two things. First, who doesn’t like free booze. Second, the definition of casual information varies wildly by who reads it. I would’ve happily drunk my margarita on the rocks solo at the W, which is why I threw my invite into Twitter, but it turns out twelve folks took my casual request and made it essential.

My second Twitter use case involves keeping track of distant friends. A few years ago, I interviewed Brent Simmons, who is the creator of, among other things, NetNewsWire. I like Brent. (Hi Brent!) My gut instinct tells me that if Brent and I worked at the same company, we’d do lunch… a lot. Still, Brent is in Washington and I’m in Los Gatos and that means the extent of our relationship is that each WWDC we end up at some bar for 15 frenetic minutes doing a year of catch up.

When Brent showed up on Twitter, I immediately started following him because I care what Brent thinks. Yeah, he’s had a weblog forever, but the casual information relayed via Twitter is far more real. The act of creating casual information is a real-time slice of your life of the moment. I read messages in Twitter and think that people are giving themselves a headline or a title of a chapter of their lives. Here are the last three on my screen right now:

• Absorbing Jared’s Hometown
• A Bit Early for the Cure
• The Wife’s Margarita Recipe

Twitter gives me a glimpse into the lives of an interesting collection of people across the planet. It’s casual information, but it’s also a bit of poetry and it’s all better than radio silence. I’d prefer to be drinking with y’all, but I’ll take what I can get.

Social without the Network

In the vast sea of social networking tools, Twitter stands apart because of what it chooses not to do. I like Facebook. It’s friendly, it’s authentic, and it gives me interesting slices of data about the lives of the people in my network. I like Ning, too. I like their focus on easy network building, I like how they actively care, and I think they could’ve gotten more than $44 million.

Still, both Ning and Facebook throw a tremendous amount of crap between myself and my network. Ok, so it’s not crap. It’s a pile of choices, and whether it’s an ad or a video or whatever content the network wants to throw at me, a choice is a decision and I have very little time for more decisions in my day. All I want is to know what these bright people in my network are up to. That’s it.

Twitter is all the social with very little network.

Keynote Kung-fu

It’s WWDC season and that means Keynote. Lots of it. Today is Sunday and I’ve clocked 6 hours of Keynote and I’m ok with that. Keynote doesn’t get in my way and Keynote doesn’t piss me off, so I’m taking a break from endless slides to give Keynote some credit and to give you some Keynote tips.

If you’re a power Keynote user, you can skip this piece. This is basic Keynote blocking and tackling.

Prepare Your Workspace

If you settling into a long Keynote session, I will now save you 10 minutes. Turn on the following palettes: Inspector, colors, and fonts. 90% of the tweaking you’re going to need to do is in these palettes and rather than switching them on and off, I want you to find a comfortable place on your desktop. Me, I put the inspector and colors next to each other with fonts below. It’s tidy.

After you’ve got your palettes set-up, let’s head over to preferences and save you some time there. I run with standard preferences except for the rulers. Go ahead and click there now.

There are three things I change here before I begin. First, I change the alignment guides to a different color. The default yellow is distraction and often conflicts with objects on the page. I use a sky blue.

Second, I turn on both “Show guides at object center” and “Show guides at object edges”. Enabled these last two preferences create all sorts of alignment guides when you move an object around the page. These guides are one of my favorite features because I have grid issues. It’s hard for me to leave a page without things aligning just-so and the plethora of alignment guides makes my alignment job easy.

Explore the Inspector

The use of color and font palettes is obvious, but you probably don’t know everything which is going down in the inspector. Take a few minutes to explore each of the panels and understand their function. This is where the cool goes down. Some random cool:

• Hate your slide size? You can change it on the document panel.
• Love transitions? Remember that there are two major animation panels: one for the slide transitions and another for per-object build transitions.
• The build panel is the heart of transitions in Keynote. This is where you set per-object transitions, but most folks don’t know that you can get really crazy by opening up the ‘More options’ drawer. The drawer allows you to see all the transition on the current page, lets you reorder them, and let’s you chain transition events together. More on this in a second.
• I know I told you to put the color palette up and you’re going to want to click on it, but you often need to specify the object you want to change in the inspector before you can change the color. Remember, if the color isn’t changing, you need to select in the inspector first. You’ll get used to it.

My last piece of advice regarding the inspector is to play because that is how you’ll get creative. If you’re wondering if you can change the opacity of that photo, go ahead and try it out. You probably can.

Organize Your Iteration

My slides always start as an outline and the fact that I can easily indent and group slides via the navigator means I can easily iterate through thoughts as they cross my mind. Like any good outliner, simply hitting tab indents a slide or a slide group — shift-tab does the opposite.

As my slide set evolves I’m constantly moving slides around as well as adding and deleting content. Often I have a slide which has a thought I want to keep around, but I don’t want to include as part of the presentation. Right clicking on the slides gives you the option to skip a slide. This removes the slides from the presentation, but not from the slide set. Handy.

If you’re working on a text heavy presentation, you can always switch to outline view in the navigator. This displays text only in the navigator and is useful in early versions of slides where all your scrubbing is ideas and not visuals.

Lastly, as random thoughts which don’t have a home show up, I’m torn between sticking them into stickies or dropping them in the presenter notes. The sticky approach has the advantage of being in your face whereas presenter notes scale. Presenter notes also show up in the presenter view which might be the single best reason to use them.

Pull It All Together with The Fade

A sure sign of a Keynote rookie is transition insanity. This is when every single slide and object has it’s own transition and it’s a visual mess. Defining a design aesthetic for Keynote is beyond the scope of this brief mental break of a piece, but I will say, “The best transitions are the ones you don’t see”.

One of my favorite combined transitions is the fade. This is when you choose to emphasize or de-emphasize an element on the page by changing the opacity. This is easy now that you’ve discovered the ‘More options’ drawer in the Build palette. Let’s try it:

• First, duplicate the object you want to de-emphasize. Set the opacity on the duplicate to whatever you want it to eventually be.
• Second, select the original object and set the Build Out transition to Dissolve. Now, move the duplicate object directly on top of the original.
• Run the presentation and see what you’ve got. A nice fade on your original object, but let’s also emphasize another object.
• Add another object to page and put a Build In transition of Dissolve.
• Now go into the Builds drawer and note you have two transitions there. Select the second transition and select the Start Build drop down and choose the “Automatically with build 1” option.
• Finally, select the first transition and select “On Click” from the Start Build drop down.

Run the presentation and see what happens. You’ve combined two transitions into one into a pleasing fade. AAAaaaaah. Simple, clean, and easy.

Ok, back to work.

How To Not Throw Up

As soon as you decide to become a professional nerd, either via a university degree or simply because you sit up all night writing Python to scratch your particular technical itch, you think you absolve yourself of having to stand up in front of a group of people make a presentation.

And you might be right.

Then there’s a chance you’re going to build or think something brilliant, and no mailing list, weblog, or wiki is going to be able to contain this brilliance. Those who want to hear about your brilliance are going to insist that you stand in front of them and explain this bright thing that you did or thought.

Conflict. Yes, you want to explain your brightness, but, um, the last time you stood in front of people and told a story was Ms. Randall’s 11th grade English class, and you stumbled through an incoherent ramble about Henry David Thoreau and some pond.

Unlike that pond, you are immensely qualified to talk about your topic, but you’re totally unqualified to present in front of a group of people. It’s not just that you haven’t had the practice, but that lack of practice has given you the erroneous impression that there’s a good chance you might throw up if you have to stand up and tell a story in front of 500 people.

Not Throwing Up is a Two-Phase Process

This article is about presentations, not content. Both are equally important, but I’m not here to help you write your content, I’m here to transform that content into a presentation that doesn’t suck.

Let’s say you’ve written your 30 slides. A rookie presentation move is to: a) have too many slides, and b) stuff your slides with clutter, like wordy bullet points. Filling each slide with as much content as possible. This is your feeble attempt to get out of actually presenting. Your thought is, “Fill the slides with information and read the slides”. This makes sense to you, since I know you’re nervous, but my question is, “Why are you nervous?”

“I’ve never presented in front of 500 people.”

“So, you’re not confident you can do it?”

“Right.”

“Ok, so let’s focus on the confidence rather than creating more horrible slides.”

Phase 1: Practice endlessly. Confidence is going to come not when you memorize your slides, but when you move the content from one side of your brain to the other. Right now, your slides are sitting in the linear left side of your brain, the practical side. This is a fine place for the slides to be while you’re creating them, but before you get up on stage, you need to move them to the right side of your brain, the creative side. You need to be able to feel your slides.

Your presentation is storytelling. It’s a performance. It’s you on stage telling me and 499 of my friends a story about why you’re brilliant. That’s not a comforting thought since I know you’re already nervous about standing in front of 500 people and bumbling through your slides. And now you’re saying it’s a performance? My presentation regarding huge performance wins in garbage collection is NOT a performance.

Of course it is. Why else would there be 500 people sitting here wanting to hear about it? I promise there’s some art, some performance, in your presentation, and the best way to find it is to practice endlessly. The best way to do that is to stand up, walk around your office, and give your presentation to no one. Over and over again.

It takes some getting used to — pacing around your office or hotel room listening to your own voice — but that’s exactly what your audience is going to hear. You need to figure out how to listen to yourself tell a story while also critically listening to the story. You’re the presenter and the audience. Yeah, it takes practice.

Start with those three slides there about that one specific topic: Talk through it and listen to how it sounds. Does it make sense? Does it flow? Are you reading the slide or are you telling a story? How does it transition into the next point? After you’ve heard yourself verbally walk through a topic a few times, you start to hear what you’re trying to say, and you make discoveries like, “Uh, I’m making no sense” and “This is supposed to be funny, but it’s lame”, or “This topic doesn’t have any relation to anything near it.”

We’re talking hours of practice here, but you’ll slowly start to notice that you’re not just memorizing the content, you’re also memorizing the flow. You’ll start to notice where you’re repeating yourself, you’ll find key points in the strangest places, and you’ll stop to reorder and rewrite slides… a lot. Good. Keep practicing.

When you can sit at your desk with your eyes closed and talk through any one of your slides, you’re going to stop worrying about what you need to say and focus more on how you’re going to say it. This intimate knowledge of your content is going to give you confidence.

But you still might throw up.

Phase Two Throw-up Avoidance

A few years back, I gave a recruiting presentation at two different universities on the same day. Same presentation, same general age group of students, morning versus evening.

The morning presentation was in front of a packed room. Just after 10am. I was three cups of coffee into the day and so was everyone else. Three slides in and I knew this was going to be an easy presentation. Heads were nodding, laughs were coming from the least expected slides, and folks were actually taking me up on my offer: “Stop me if you have a question”. Captivated. 40 minutes of slides. 20 minutes of intense, engaged questions and answers. Mission accomplished.

5 hours later. I’m in another conference room 50 miles away in another university and everyone’s coffee has worn off. The room is half full and I’m a little tired, but I’ve done this presentation 30 times in my head, so when I start on slide #1, it’s on. I know this presentation, so why is everyone falling asleep on slide #3? There’s no laughing and, by slide #10, someone gets up and walks out. Ouch.

Hopefully, this is normally when you considering throwing up. I say hopefully because there are a great many presenters who don’t have a clue when the presentation is going badly. This is certainly a rookie mistake, but I’ve sat through a fair share of presentations by seasoned managers where they just flopped and didn’t have a clue.

You need to stop and listen to what your audience needs. If your presentation isn’t going swimmingly, stop five minutes in and look around the room. Is the audience looking at you? Or are they staring at their laptops? Has there been nodding? I know it’s been 10 seconds now and you’re still looking at the audience saying nothing — it’s ok, they’re just sitting there wondering if you’re about to throw up. You’re building tension.

More importantly, you’re figuring out the most important part of your presentation: which audience showed up? Here’s the rub: you can write brilliant, compelling slides, you can practice your slides 40 times, but you can never predict who is going to show up, and your presentation must be tailored to those who show up.

Ok, now throw up.

Phase 2: Improvise. This is hard and this is where our senior managers, with hundreds of presentations under their belts, screw up. First, they’ve stopped fretting, which means their presentations lack any sort of energy. Consequently, they don’t listen to the audience, so when the audience asks for something, they don’t give it. This is why they sound like bad used car salesmen; they’re just reciting the sales pitch and they don’t care what you think.

How do you need to improve? What is your audience going to ask for? They want one thing: they want to participate. No, they don’t want to get on stage and present your slides; they want to be included in this presentation — in this performance. I’m not talking about waves of applause, I’m talking about taking looking at a sea of people and knowing these people are listening to your every word. It’s a constructive silence directed squarely at you, and when you learn how to read it, it’s a high.

So, what are you going to do? How are you going to adapt? Maybe this crowd wants you to wake them up? How about accentuating your points loudly? How about a bit more walking around the stage waving your hands furiously? Perhaps you’re too amped and they want you to slow and pause between your words. Give them time for your words to soak in.

When someone walked out of my university presentation, I immediately stopped. I began reminiscing about my college years and the complex protocol I’d worked out for when it was ok to walk out of a lecture. This 5-minute irrelevant segue did two things: first, it reminded my semi-lucid audience that I was one of them, and second, since my segue was timely (person walking out) and humorous (maybe), we reconnected. They woke up and I dove back into my slides with my new college buds who were now clear that I cared about what they thought.

Fret

No lying. The ability to improvise takes experience and you’re going to have to live through and recover from a couple of horrific presentations in order to build up your improv repertoire. For these early disasters, I have three pieces of advice:

• When you’re presenting, talk like you’re talking to one person who happens to have a thousand eyeballs. Don’t get lost in the sea of faces, pick a person and tell them the story. Not for the entire hour, just a few seconds. Then move on.
• Use silence as punctuation. My favorite trick in the book especially since I’m a fast talker. When you hear yourself gaining verbal momentum, stop. Count backwards from 5. Walk across the stage. Resume. These breaks are going to give both you and your audience a chance to mentally regroup.
• They want you to succeed. This piece of advice is in every presentation guide out there — because it’s true. Your audience is expecting you to rock their socks. They’re expecting an A+. That’s where you’re starting in their heads and walking on stage knowing this helps.

I don’t want you to throw up.

I want you to fret about this presentation, and if you’re not losing a little sleep, you don’t care. You’re not going to be motivated. You’re going to end up perpetuating the idea that nerds can’t tell a story. If you’ve been handed the responsibility of a presentation and aren’t the least bit concerned, give it to someone who is going to sweat this thing and then be prepared for that person to end up as your boss.

The Rules of Toys

Ok, stop reading right now and count the toys you can see from your desk. Don’t ask me for a definition, just count.

Ordered by proximity, I’ve got:

The amethyst ball the Mom gave me.




A hockey stick given to me by a prior team. Near this hockey stick is a hockey puck.



A cup-sized brass bell along with a small bell-ringing device.

What’s your count? Zero? Really? Loosen up your definition and try again. Thirty? Wow, do you ever get any work done?

For me, toys are yet another means of a mental punctuation. As I slowly page through my day, I engage these toys for a mental break. The amethyst ball is my tactile fidget “not sure what to do next” device; the hockey stick is my “break the cycle of sitting at the desk and score one for the New York Rangers” break; and the bell, well, you’ve got to hear the bell to understand that it’s the perfect musical mental reset.

I’ve had various toys in my office since I started in high tech, but it’s only in the last six months that I’ve discovered how we can use the rules of toys in both interface and application design.

The Rules of Toys

A well-designed toy:

• Makes a request. It asks you to “Play with me”. This is why you are compelled to touch it.
• Is fantastically straightforward. The design suggests, “When you pick me up, it’s going to be clear what’s going on.” This is why great toys never have manuals.
• Has hidden potential. A toy is going to hook you with some clever visual, but the real value is something you can not see, but must find.
• All of this leads to the fact that a well-designed toy is instantaneously fun and who doesn’t want to have fun?

Now there are very different kinds of fun that a toy imparts. The monkey fun we get out of throwing a frisbee feels different than the Einstein fun of figuring out the Rubik’s Cube, but regardless of where you park the fun in your brain, you’re still playing with a toy.

While it’d be entertaining to design all products and user interfaces with these rules in mind, we’d never actually get anything productive done. It’d be really hard to listen to your music if the interface was a Rubik’s Cube. Or maybe not… wait, someone write that down. The point is that you need to be selective where you apply the toy rules and the best way to explain this is to show you how it’s done.

Any Idea What This Is?

Pandora. Once you’ve selected a song or an artist, Pandora starts merrily playing your related music via their music player. Invariably, Pandora will play something you hate and you’ll want to get rid of it, so you’ll check out the interface where your mouse will hover over the cover art and you’ll see this:

This is a toy interface. It’s straightforward, it’s simple, it’s not exactly clear what’s going to happen when you start clicking on those thumbs, but you’re being invited to do something.

Yes, you have cultural touchstones as to what “thumbs up” and “thumbs down” means and this gives you some idea what clicking one or the other will accomplish, but, more importantly, these thumbs empower you to make a difference, make a judgment even if you might not understand exactly why. There’s a silent contract that by clicking on these little playful glyphs that you’re going to somehow improve your Pandora musical experience.

Let’s keep moving…

Any idea what this is?

“No, Rands, but I just want to reach out and touch it.” Me, too.

This is iPulse. It’s a system monitoring utility from Iconfactory, which is arguably the king of toy application development.

Now, a screenshot isn’t a fair means of analysis of iPulse because its interface isn’t static, and the application is an interactive experience. As you run your mouse over the interface, you see all sorts of statistics regarding your system. But at a glance, the design of iPulse is a toy. It’s encouraging you to explore. There are system monitoring tools out there that spam you with all sorts of statistics regarding your memory, hard drive space, and network activity, but the iPulse approach is the opposite. They start with a question, “What if understanding how your computer worked was an exploration?”

No, this design isn’t for everyone. Hardcore performance nerds are going to be quite happy running top in a terminal window, whereas iPulse uses a playful design to hide the nerdery behind a toy and give you a chance to learn. In the middle of the day, when iPulse is pulsing and blinking in the corner of your screen, you’re going to start to tinker with it and you’re going to discover, “Hey, Mail.app has totally lost its mind and is eating my CPU. Now what?”

The hidden consequence of playing is that you learn, and how would you prefer to learn, from a textbook or a toy?

The examples so far demonstrate the toy rules for portions of an application or for a simple utility, but the real question is: can you build an entire application using the toy rules? Sure you can.

Twitter is a Big (Important) Toy

Let’s see if Twitter obeys the rules:

Does it make a request?

Is it fantastically straightforward?

Doesn’t get much simpler than that.

Does it not present obvious value (but it’s there)?

The blogosphere can’t shut up about whether there is value in Twitter or not. Like weblogs, the opinions range from “It’s a fad” to “IT’S GOING TO CHANGE MEDIA AS WE KNOW IT”, but neither is the lesson.

The first lesson is that the fact that folks can’t shut up about Twitter means there is obvious value, even if no one can articulate what that value is. The second lesson is simply that people like to play, and Twitter is a communication medium designed as a toy, which leads us to the last rule…

Is it fun? Yeah, it is fun. Forget about the organic social network that springs up around you, forget about Twitter’s current spotty performance, and realize it’s fun to summarize your mental state every hour or day. Think of it like this: if you had to give your state of mind a chapter title, what would it be?

Twitter is also a reminder that there’s another toy rule that I haven’t mentioned. In its hidden potential, a well designed toy allows each person to build their own unique experience.

Choosing When To Play

Designing with the toy rules is not a solution for all design problems. You might want to employ the toy rules when it’s important that your users not only focus on part of your interface, but it’s also important that they remember it. Giving your users a toy, an interface that is going to invite them to play, is also going to invite them to explore, and when they’re exploring, they’re learning.

Toy interfaces are also great at turning a terribly complex idea into a simple interface. Yeah, you might lose information fidelity by tucking your complexity inside a toy, but would you rather your users stop at confused, or would you prefer to give them a chance at discovery? Again, the value of any toy is not obvious, it must be discovered. No, it must be a joy to discover.

More Messy Thinking

Let’s start with the visual…

This new monitor configuration keeps popping up the engineering team and after walking into enough offices thinking, “Useful or flashy?”, I decided to give it a whirl.

The basic usage pattern is unchanged. The left screen is for the active workspace whereas the right screen is the palette screen — utility windows like calendar, Twitter, instant messaging, and stickies which require a glance now and then, but aren’t playing in the primary workspace.

After getting over the initial shock of the verticalness of the right monitor, I have the following thoughts:

• The windows you see on that monitor are unchanged in terms of shape from the original configuration. They tend to be tall, narrow windows which means they fit perfectly on the rotated monitor and they have new room to grow.
• While this screen shot doesn’t show it, the vertical monitor is a great space for scads of semi-translucent terminal windows. MmmmmmmMMm Terminal Windows.
• That’s the stand of the monitor jutting off the right hand side of the picture. I haven’t looked at how it’s attached to the monitor to see if it’s non-trivial to remove, but the resulting angle of the monitor leaning back against the bookshelf is, well, pleasant. It’s leaning back more than the primary workspace and it gives the monitor a relaxed attitude.
• It’s likely a result of the new shape, but I’m suddenly feel I’ve discovered the bottom of the right monitor.

You can see the evolution of my desktop as well as my fascination with baseball caps here and here, but it’s more important to understand why you need all these pixels by reading the original Messy Thinking article.

The Sanity Check

As we discovered in A Glimpse and a Hook, it’s almost a miracle when the phone rings and a recruiter wants to set up a phone screen. The fact is, someone, somewhere in the organization has successfully mapped you to an open position. This is a really big deal because, in my experience, the chance that you’ll get this job has improved logarithmically. It’s not 50/50, but it’s vastly better than when you were a random resume sitting on a desk.

There’s a sense of relief when that phone call arrives and as soon as you hang up the phone with the recruiter, you’re going to call your best friend, “Hey, I got a interview with The Company!”

No, you didn’t. You got a phone screen and a phone screen has little to do with an interview. While your situation isn’t as tenuous as the 30 seconds you have to make an impression with your resume, you’re still not in the building and nothing real is happening until you’re in the building.

Like Glimpse, I’m going to walk you through my precise mental process that I use as I walk through the phone screen, but first you’ve got homework:

Stalk Your Future Job

Before you even talk to me, you’re on a fact-finding mission. You’ve got a job description, and after the phone screen has been set up, you’ve got my name. You might also have an idea of the product or technology associated with this gig or you might not, but even without a product name, you’ve got plenty of information to start with.

Do your research. Google me. Find out anything you can about what I do and I what care about. This isn’t stalking, this is your career, and if I happen to be an engineering manager who writes a weblog, well, you can start to learn how I think. Maybe I don’t have a weblog, but I post to mailing lists. That’s data, too.

How is this going to help you during the phone screen? Well, I don’t know what you’re going to find, but anything you can gather is going to start to build context around this job that you know nothing about. This helps with phone screen nerves as well. See, I have your resume and you have nothing. Aren’t you going to feel better about talking with a total stranger when you figure out from staring at my Flickr pages that I absolutely love Weimaraners? Isn’t it going to be reassuring to know I swear in my Twitters? A bit of research into who you are talking to is going to level the information playing field.

Similarly, if you have a product name or technology, repeat the same process. What is the product? Is it selling well? What do other people think about it? I’m not talking about a weekend of research here. I’m talking an hour or so of background research so that you can do one thing when the phone screen shows up: you need to ask great questions.

That’s right. In your research, you want to find a couple of compelling questions, because at some point during the phone screen I’m going to ask you, “Do you have any questions for me?” and this is the most important question I’m going to ask.

Initial Tuning

Before I ask you the most important question, I need to figure out a couple of things early in our chat. What I need to learn is:

Can we communicate? I’m going to lead off with something simple and disarming. It’s either going to be the weather or something I picked up from your extracurricular activities. “Do you really surf? So do I! Where do you surf?” These pleasantries appear trivial, but they’re a big deal to me because I want to see if we can communicate. It’s nowhere near a deal killer if the pacing of our conversation is awkward, I’ll adjust, but how off is it? Are we five minutes in and we still haven’t said anything? Ok, maybe we have a problem.

One more softball. My follow-up questions will now start to focus on whatever question your resume left me with. I’ve no idea what I’m going to ask because it varies with every single resume, so my thought is that you should have your resume sitting in front of you because it’s sitting in front of me as well. It’s my only source material.

Whatever these follow-up questions are, I’m still figuring out how we communicate. This means you need to focus on answering the questions. It sounds stupid, but if it’s not absolutely clear to you what I’m asking, it’s better to get early clarification rather than letting me jump in five minutes into your answer to say, “Uh, that’s not what I was asking.”

See, you and I are still tuning to each other. It’s been ten minutes now, and if we’re still not adjusted to each other’s different communication styles, I’m going to start mentally waving my internal yellow flag. It doesn’t need to be eloquent communication, but we should be making progress.

No more softballs. We’re past the softball phase of the interview and now I’m going to ask a hard question. This isn’t a brainteaser or a technical question; this is a question that is designed to give you the chance to tell me a story. I want to see how you explain a complex idea over the phone to someone you don’t know and can’t see.

Again, who knows what the actual question will be, but you need to be prepared for when I ask the question that is clearly, painfully, open-ended. I’m not looking for the quick, clean answer; I’m looking for a story that shows me more about how you communicate and how you think. Being an amazing communicator is not a part of most engineering jobs, I know this. I’m not expecting Shakespeare, but I am expecting that you can confidently talk about this question because I found this question in your resume and that is the only piece of data we currently have in common. If we can’t have an intelligent discussion about that, I’m going to start wondering about the other ways we aren’t going to be able to communicate.

Your Turn. We’re twenty minutes into the phone screen and now I’m going to turn it over to you when I ask “Do you have any questions for me?”

When I tell friends that this is my favorite question, the usual response is, “So, you’re lazy, right? You can’t think of anything else to ask, so you go for the path of least resistance.” It’s true. It an easy question for me to ask, but it is essential because I don’t hire people who aren’t engaged in what they’re doing. And if you don’t have a list of questions lined up for me, all I hear is: YOU DON’T WANT THIS JOB.

A well thought out question shows me that you’ve been thinking about this job. It shows me you’re already working for it by thinking about the job outside of this 30-minute conversation. Yeah, you can probably wing it and ask something interesting based on the last 20 minutes, but the impression you’re going to make with me by asking a question based on research outside of this phone screen will make up for a bevy of yellow flags. It shows initiative and it shows interest.

The Close

And we’re done. It went by pretty quick, but the question is, “How’d it go?” Here’s a mental checklist to see how you did:

Long, awkward pauses. Were we struggling to keep things moving? Were there long silences? Well, we didn’t tune appropriately. Again, not a deal killer, but definitely a negative.

Adversarial interactions. What happened when we had different opinions? Did we talk through it or did we start butting heads? This happens more than I expect on phone screens, and it’s not always a bad thing. I’m not interested in you telling me what I want to hear, but if we are on opposite sides of the fence, how do we handle it? If a candidate is willing to pick a fight in a 30-minute phone screen, I’m wondering how often they’re going to fight once they’re in the building.

How’d it feel? This is the hardest to quantify, but also the most important. Did we click? Did the conversation flow? Did we both learn something? Ideally, I’m a decent representation of the culture of the team I’m hiring for, so if the 30 minutes passed painfully, I’m wondering what kind of pain hiring you might inflict on the team.

Specific next steps. How did I leave it? Did I give you a song and dance about how “we’re still interviewing candidates and we’ll be in touch within the next week”? Well, that’s ok, but what you’re really looking for is a specific next step like “I’m going to bring you in” or “Let’s have you talk with more of the team”. An immediate and actionable next step is the best sign of success with a phone screen. If I don’t give you this as part of the close, ask for it. If I stall, there’s a problem.

A phone screen is not a interview, it’s a sanity check. I already know you meet the requirements for the job by looking at your resume. The phone screen is going to tell me whether you meet the requirements of the culture of my team.

Unlike your resume where you send your hope to an anonymous recruiting address, the phone screen gives you leverage. The phone screen is the first time you get to represent yourself as a person. It’s still a glimpse, but it’s the first time you can actively participate in your next job.

A Glimpse and a Hook

The terrifying reality regarding your resume is that for all the many hours you put into fine-tuning, you’ve got 30 seconds to make an impression on me. Maybe less.

It’s unfair, it’s imprecise, and there’s a good chance that I make horrible mistakes, but there’s a lot more of you than me, and while hiring phenomenal teams is the most important thing I do, I’m balancing that task with the fact that I need to build product and manage the endless stream of people walking into my office.

But here’s a glimpse. I’m going to walk through the exact mental process I use when I look at a resume. I don’t know if this is right or efficient, but after fifteen years and staring at thousands of resumes, this is the process.

The First Pass

Your Name. It’s simple. Do I know you? Whether I do or not, I’m going to immediately Google you to see if I should. Oh, you a have a weblog. Excellent.

Company Names. Do I recognize any companies that you worked at? If I do, I don’t look at what you actually do, I assume that if I recognize the company, I’m in the ballpark. If I don’t know the company, I scan for keywords in the description to get a rough idea. Hmmmmm… networking words. Ok, you’re a networking guy.

Job Description and History. Here I’m looking for history and trajectory. How many jobs have you had and for how long? How long have you been in your current role? Where’d you come from? QA? Or have you always been an engineer? This is when I start looking for inconsistencies and warning flags.

Other Interests and Extracurriculars. Yeah, this is part of the first pass. I’m eagerly looking to find something that makes you different from the last fifty resumes I looked at. More on this in a moment.

So, we’re done. It’s been ten to twenty seconds and I’ve already formed an opinion. There’s a good chance that I’ve already made a call whether to move forward on you. If there are other folks checking the resume out, I can certainly be convinced to take a second look, but a basic opinion has been formed.

Before we move to the second pass, let’s talk about the parts of your resume I didn’t look at and never will.

Professional objective. This is likely your lead paragraph and I skipped it. Career center counselors across the planet are slamming their fists on their desks as they read this because they’ve been telling students, “You need to write a crisp career objective. It defines your resume.”

Yes, it does, but I still don’t read it and it’s not because there isn’t good content there, it’s the time issue. See, if your resume is sitting in my inbox it means someone has already mapped you to an open job in my group. Reading your objective is going to tell me something I already know. Besides, my job title and description scrub will tell me whether we’re in the ballpark or not. If I’ve got a Jr. Engineering position open and you’ve got 10 years experience, I’ll figure out that mismatch when I look at your history.

This doesn’t mean you shouldn’t include this objective in your resume. As you’ll see below, there’s more to the process than just me reading your resume, and different folks are looking for different content.

Skills. I skip the skills section not only because this is information I’ll derive from job history, but also because this section is full of misinformation. I’m not going to say that people lie in the skills section, but I know that if a candidate has heard the word Linux in the workplace, there’s a good chance they’re going to put Familiarity with Linux as a skill on their resume.

Besides, again, I know you’ve goofed around with Linux because you said so in the description of your last job, right?

Summary of Qualifications. Similar to Skills, this is another skip section for me. Here’s a good example from an imaginary resume: “Proven success in leading technical problem solving situations”. This line tells me nothing. Yes, I know you’re trying to tell me that you’re strategic, but there is no way you’re going to convince me that you’re strategic in a resume. I’m going to learn that from a phone screen and from an interview.

Unlike Skills, which I find to be a total waste of time, I will go back to Summary of Qualifications if we end up talking. When you write “Established track record for delivering measurable results under tight schedules”, I am going to ask you what the hell you mean on the phone and if your answer isn’t instant and insightful, I’ll know your qualifications are designed to be buzzword compliant and don’t actually define your qualifications.

The Second Pass

If I can’t decide whether to schedule a phone screen after the first pass, I go for another. The goal now is, “Ok, I saw something I liked in the first pass, is it real?” This is when I do the following:

In-depth Job History. I’m going to actually read the job history for the past couple of jobs. Not all of them, just the last two or three. What I’m doing is fleshing out my mental picture of you. I’m looking for more warning flags. Do your responsibilities match your title? How long were you at your most recent job? If it was a long time, can I get a sense of how you grew? If it was short, can I figure out why you left? Do your last two jobs build on each other? Can I get a sense of where you’re headed or are you all over the place?

Your job history, — your professional experience — is the heart of your resume. This is where I spent my time vetting you and this is where you should spend your time making sure I’m going to get the most complete picture of who you are and what you’re going to bring to my team.

School. Yeah, this is the first time I’ll notice whether you went to college or not. I purposely do this because I’ve found over years of hiring that a name brand university biases my opinion too early. There’s a lot to be said for a candidate who gets accepted to and graduates from Stanford or MIT, but I’ve made just as many bad hires from these colleges as great ones.

Seeing a non-Computer Science degree is not a warning flag. In fact, I’m a huge fan of hiring physics majors as engineers. For whatever reason, the curriculum for physics has a good intersection with computer science. Any technical major for me is perfectly acceptable, and even non-technical majors with a technical job history make for a resume worth thinking about.

Ok, so that second pass took another 15 to 30 seconds and we’re done. You’ve just given me the opportunity to change your life by potentially bringing you in for an interview and that chance is over. Next!

What’s unfair about what just happened is this. You spent hours working on your resume. You sent it to close friends for review and you edited it. You agonized over the different sections and you stressed about the tone, and here I am, the hiring manager, and I read 1/10th of your work in 30 seconds.

Don’t despair. There are some easy things you can do to improve your chances.

Differentiate, Don’t Annoy

Design your resume to downgrade. Your resume needs to withstand some formatting abuse. Go get your resume right now and convert it to plain text. Can you still see the different sections? Is your job history still cleanly formatted? Can you still see the different jobs as well as the start and stop dates? Screw around with the margins, too. Where are your line breaks? They’d better not be after every line because that means visual chaos if a well-intentioned recruiter starts messing with fonts.

Never include a cover letter. I don’t read them. Recruiters don’t pass them on. Make sure the key points of your cover letter are living in your career objective and your job history.

Embrace honest buzzword compliance. Remember, I’m not the only who is going to read your resume. I’m likely the most qualified to make a call whether you’re a fit for my job, but before your resume gets to me, its going to be passed through a couple of different recruiters and these folks are just as busy as I am.

The lifeblood of the recruiter is the keyword. Java, C++, Objective-C. The more specific relevant keywords and buzzwords you can shove into your resume, there more likely you’re going to make it past the initial cut.

As I said above, I skip the Skills section because most folks already know that recruiters are just searching for specific words when they’re sourcing candidates, so they shove every possible buzzword into their resume. Know this, if you claim to Strong Java Background in your resume, I’m going to be compelled to figure out how strong your skills actually are. Don’t include any keyword or buzzword that you aren’t comfortable talking about at length.

Differentiate, don’t annoy. You’re likely going to start developing your resume from a template. Maybe you’ll use a friend’s resume that you like as a starting point. Excellent. How are you going to make it yours?

Remember, I’ve looked at thousands of resumes, which means I’ve seen all the standard templates. I know when you’re using Microsoft Word and I know when you’ve developed a format of your own. Right this second, I’m flipping through a dozen college resumes and the ones I’m spending time on are the ones that grab me visually, where there is something different. On this one, the fellow put a subtle gray box around each of his section headings. On this other one, the candidate used a nice combination of serif and sans serif fonts to grab me.

A couple of subtle visual differences to your resume goes a long way toward keeping me engaged in reading it, but remember, we’re engineers here and efficiency matters. Differentiating your resume to the point that I can’t quickly parse it is going to frustrate me. You’re not applying to be a visual designer; you’re an engineer. Keep to the standard sections and don’t make me work to figure out who you are.

Sound like a human. Here’s a doozy, this intern says he “planned, designed, and coordinated engineers efforts for the development of a mission critical system”. ZzzzzzzzzzZzz. What did this guy actually do? I honestly don’t know. Let’s call this type of writing style resume mumbo jumbo and let’s agree that usage of this style is tantamount to saying nothing at all.

What was the mission critical system? Why was it critical? How in the world did an intern plan, design, and coordinate the engineering efforts? I’m a fan of giving interns real world work, but it’d take a world-class intern to plan, design, and manage engineers on whatever this mission critical system is.

Take time to write your resume for a human. You need to hit all the right buzzwords and keywords to get yourself past the layers of recruiters, but I’m the guy who is really going to take apart your resume, and if you’re saying nothing with resume mumbo jumbo, I’m learning nothing. Give me specifics and give them to me in a familiar tone. I’m not an automaton; I honestly want to know what you do. Tell me a story.

Include seemingly irrelevant experience. This applies mostly to college types who lack experience in high technology. You’re going to stress that your job history doesn’t include any engineering and you’re thinking your summer working at Borders bookstore is irrelevant. It’s not. Any job teaches you something. Even though you weren’t coding in C++, I want to know what you learned by being a bookseller. Was it your first job? What did you learn about managers? How did you grow from the beginning to the end of the summer? Explain to me how hard work is hard no matter what the job is.

A Glimpse and a Hook

A resume will never define who you are. It’s not the job of your resume to give me a complete picture, and if you’re struggling to include every last detail about who you are, you’re wasting your time. Your resume should be designed to give me a glimpse and a hook.

The glimpse is a view into the most recent years of your professional career. It should convey your three most important accomplishments and it should give me a good idea where your technical skills lie.

The hook is more important. The hook will leave me with a question. Maybe it’s something from your other interests section? How about an objective so outlandish that I can’t help but set up a phone screen. I’m not suggesting that you make anything up, I’m asking you to market yourself in a way that I’m going to remember. A resume is not a statement of facts. It’s a declaration of intent.

Technicality

There’s a very short list of new manager “must do’s” in the Rands Management Rule Book. The brevity of this list comes from the fact that a must is an absolute and, when it comes to people, there are very few absolutes. A clever way to manage one person is a disaster when applied to another. This makes the first item on the Management Must Do List:

Stay flexible.

The only constant in management is that believing you’ve seen it all is a bad idea. Staying flexible is the only stance to adopt when constant change is the only constant.

Paradoxically, the second item on the list is surprisingly inflexible and it’s still a personal favorite of mine because I believe it helps set the stage for management growth. It reads:

Stop coding.

The theory is this: if you want to be a manager, you must learn to trust those who work for you to take care of the job of coding. This advice can be hard to digest, especially for new managers. It’s likely that one of the reasons they became managers is due to their productive developers, and their first reaction when things go to crap is to revert to the skills that built up their confidence. That’s writing code.

When I see a new manager fall back to coding, I tell the manager, “I know you can code. The question is, can you manage? You’re no longer responsible for yourself, you’re responsible for the team, and I want to see you figure out how to get the team to solve this problem without you coding. Your job is to figure out how to get yourself to scale. I want lots of you, not just one.”

Good advice, huh? Scale, management, and responsibility. Very buzzword compliant. Too bad I’m wrong.

Wrong?

Yup. Wrong. Not totally, but enough that I might need to make some calls to past co-workers and apologize. “That not coding pitch of mine? Wrong. Yeah. Start programming again. Start with Python or Ruby. Yeah. I mean it. Your career depends on it.”

When I began my career as a developer at Borland, I was part of the Paradox for Windows team and this was a big one. Just on the application development team we had 13 developers. If you included the heads from the various other teams who provided essential technology like the core database engine, graphing engine, and core application services, you’re talking 50 engineers directly contributing to the product.

No team that I’ve been on since then has even been close in terms of size. In fact, with each passing year, the size of the engineering teams contributing to my products has steadily shrunk. What’s going on? Are we getting collectively smarter as developers? Nope, we’re just distributing the load.

What have we, as developers, been doing for the past 20 years? Well, we’ve been writing a crap load of code. Piles of it. So much of it that we decided that maybe it was a good idea to make it easy to share by open sourcing it. Thankfully the Internet showed up which made this sharing trivial. If you’re a developer, try this right now. Go search Google Code for your name and find some code you forgot about that everyone can see. Scary, huh? Didn’t think your code lived forever. It does.

Code lives forever. Good code not only lives, it grows as those who value it make sure that it doesn’t become stale. It’s this pile of high-value, well-maintained code that is helping shrink the average size of the engineering team because it’s allowing us to focus less on writing new code and more on integrating existing code to get the job done with fewer people and in less time.

There’s a depressing line of reasoning here, the idea that we’re all just a bunch of integration automatons using duct tape to connect different pre-existing moving parts to create slightly different versions of the same thing. It’s this train of thought that has a lot of senior management teams excited about outsourcing. “Anyone who can use Google and has some duct tape can do this, so why are we paying big bucks for our local automatons?”

We’re paying these management types some pretty big bucks to think this crap up. Still, it brings up my final point that there are eager, bright developers all over the planet and they’re eager and bright even though they haven’t spent a moment in an accredited university. Oh yeah, and there lots more of them coming.

I’m not suggesting that you should be worried about your job because some bright fellow overseas is gunning for you, I’m suggesting that you should be worried about your job because the evolution of how software development occurs might be moving faster than you. You’ve been working for ten years in your job, five years as a manager, and you’re thinking, “I know how to develop software”. And you do. Right now.

Stop Coding?

If you follow my advice and remove yourself from the code, then you are removing yourself from the act of creation. This act is why I don’t really sweat outsourcing. Automatons don’t build, they process. While good process can save a lot of money, it’s not going to bring anything new to the world.

With smaller teams doing more for less, removing yourself from the code strikes me as a bad career move. Even in a monstrous company laden with policy, process, and politics, you can’t forgot how to develop software. And how to develop software is changing. Now. Right under your feet, this very second.

You have issues. I understand. Let’s hear them.

“Rands, I’m on the Director track and if I keep coding no one is going to think I can scale.”

My first question to you is this: from where you are sitting in your soon-to-be-Director chair, do you see software development changing within your company? If the answer is yes, my next question is: how is it changing, and what are you going to do about it? If your answer is no, then you need to move your chair because, I swear to you, software development is changing right this second. How in the world are you going to scale if you’re slowly forgetting how software is made?

My advice is not that you start assigning yourself tons of features in the next release. My advice is that you take action so that you stay in touch with how your team builds stuff. You can do this as a Director or a VP. More on this in a moment.

“Uh, Rands, someone has to referee. Someone has to have the vision. If I code, I’m going to lose perspective on my job.”

You still need to referee, you still need to massage decisions, and you still need to spend 30 minutes every Monday morning walking around the block four times with that engineer who needs to walk through his weekly “We’re Doomed” rant, but you also need to lose perspective about your job and you do not need to be a full time coder to do this.

My advice for losing perspective:

1) Use the development environment to build the product. This means you must be familiar with your teams tools including the build system, version control, and programming language. This task is going to keep you in touch with the language your team uses to talk about how they get stuff done. And it will also allow you to continue to use your favorite text editor… which rocks.

2) Be able to draw a detailed architectural diagram describing your product on any white board at any time. I’m not talking about the three boxes and two arrows versions. You need to know the detailed one, the hard one that isn’t pretty and is tricky to explain. This is your map for understanding just about everything about your product. It changes over time and you should be able to understand why those changes are occurring.

3) Own a feature. I’m literally cringing as I write this because it is fraught with danger, but I don’t think you can really do #1 or #2 without a feature that is yours. Owning a feature not only forces you to actively participate in the development process, it also switches your context from “Manager responsible for everything” to “Person who owns a thing”. This is a humble, unassuming perspective which will remind you about the importance of small decisions.

I’m still cringing. Someone is already yelling at me, “MANAGERS OWNING FEATURES??!?!” (And I agree.) You are still a manager, so make it a small feature, ok? You’ve still got a lot to do. If you can’t imagine owning a feature, my back-up advice is to fix some bugs. You won’t get the joy of ownership, but you’ll gain an understanding of the construction of the product that you’ll never get walking the hallway.

4) Write a test script. I still do this late in the product cycle when folks are losing their minds. This is a simple script that you run with each build. Think of it as a your checklist for understanding what your product does. Show it to co-workers. Do it often.

“Rands, if I code, I’m going to confuse my team. They’re not going to know if I’m a manager or a developer.”

Good.

I mean it. I’m happy you’re about to confuse your team by swimming in the developer pool. The simple fact is that well-defined roles in software development are fading. User interface guys are doing what can only be called development in Javascript and CSS. Developers are learning more about interaction design. Everybody is talking to everybody else and they’re learning from each other’s mistakes, stealing each other’s code, and there is no reason that a manager shouldn’t be participating in this massive global cross-pollination information cluster-fuck.

Besides, you want to be a part of a team of interchangeable parts. Not only does this make your team more nimble, it presents each person with the opportunity to see the product and the company from a vastly different perspective. How much more are you going to respect quiet Frank the Build Guy when you see the simple elegance of his build scripts?

I’m not wishing confusion and chaos on your team. I’m actually wishing better communication on it. My belief is that if you are building the product and touching the features that you’ll be closer to your team. But, more importantly you’ll be closer to how software development is constantly changing in your organization.

One Absolute

A co-worker at Borland once verbally assaulted me for calling her a coder.

“Rands, a coder is mindless machine. A monkey. A coder does nothing relevant except lay down boring lines of useless code. I am a software developer.”

She was right and she would’ve hated my advice for new managers to stop coding. Not because I was suggesting that they were coders, but more that I was proactively telling them to start ignoring one of the most important parts of their jobs: software development.

So, I’ve revised my advice. You can stop coding, but…

Stay flexible and don’t stop developing.

Interview: Allan Odgaard

I’m coming up on five years of steady Mac OS X usage and anniversaries are a time of reflection, so I went back to read my first significant article about Mac OS X.

There’s something missing from this first analysis. See, there was one killer app that I’d been dying to try out on the Mac platform and the lack of any mention in this first piece is strange to me.

It was BBEdit, people. I’d been longing to seriously develop against this editor since a brief QA stint at Symantec in the early 90s and when the time finally arrived where I had a professional reason to do so, the editor just didn’t stick.

Yes. I’m doing less coding and more managing in my current incarnation, but I use some type of editor on a daily basis, so why the constant stream of semi-criticism of an application that so many people love?

The answer is TextMate. As I wrote about in Bright, Patient Design, this editor has filled the editor vacancy on my Mac OS X desktop and I was happy to interview its creator, Allan Odgaard, to learn more about the development of my new favorite tool.

RANDS: Tell us the story of the moment you decided to develop a new editor for Mac OS X.

ALLAN: It wasn’t a singular moment. It was having worked with the Mac for maybe half a year that lead me to the conclusion, that if I wanted to make shareware for the Mac, a text editor was something where there was no native offerings, so definitely a niche to fill.

It might seem I little harsh to say no native offerings, but everything based on NSTextView is generally not much more than NSTextView which, while one of the best text editors that comes with a GUI kit, is not a feature packed editor for the power user.

As for dismissing the Carbon editors which did exist: at that time Carbon did not support sheets and drawers, did not use the standard key bindings infrastructure, often used the older Classic spacing guidelines, etc. So for me (a “switcher”) they often felt a bit out of place.

According to Wikipedia, you did 5 months of development to get a 1.0 release out the door. How’d you pick the feature set for this first release?

It was actually more like four months though I had experimented with various editor related stuff prior to that, but did start basically with a clean slate.

At that time, the primary goal was to get something released, so the features were mostly determined from a “do we really need this for 1.0?” As motivation (for writing yet another editor) I did however need 1.0 to have foldings, snippets, and recordable macros.

How has BBEdit (or other editors) influenced the design and feature set of TextMate?

A few of the things which definitely did influence me when I wrote TextMate were:

• CygnusEd: this is a very simple Amiga editor which I used a lot. It taught me the usefulness of recordable macros and how a few simple basic tools is generally better than specialized ones. As of such, you could say that initially I wanted to recreate CygnusEd for the Mac, but add features such as syntax highlight, foldings, snippets, and similar.
• VisualAssist: this is a plug-in for MSVC++ and it adds things like auto-pairing of brackets, re-indented pasting, and a lot of other neat stuff. Before I tried this plug-in, I probably would not have touched such smart features, because I would think they got in the way. But VisualAssist blew my mind, and it still does!

• NEdit: I used this at the university for everything text related, and while I was not a power user, I once took a look at how it did language grammars, which it did pretty free form, and that has stuck and was my outset for TextMate’s language grammar system. Also, the ability to execute the current line as a shell command and move around a column selection, I loved that about NEdit as well and added that to TextMate.

A big non-editor inspiration was CSS selectors which is what I recreated as scope selectors. The first time I read the CSS specification I was pretty excited to try out the concept. Unfortunately I did not have access to any browser which implemented it, so I started writing my own implementation, though I never got very far with it. Still, a seed had been planted and on an unconscious level I have probably tried to find a place where I could implement them, ever since.

There’s something very satisfying that TextMate has built-in software update. Was there any special reasoning behind this feature?

Yes, this comes from me wanting to push frequent updates, but not inconvenience the user too much. If there’s too much manual work, the user might not appreciate frequent updates and might either choose to receive less of them or just feel annoyed.

That said, it was actually Nicholas Jitkoff (of Quicksilver fame) who was bugging me about having to do the manual work each time. But I wouldn’t have spent as much time on it had it not been for what I mentioned above.

Do you have a favorite pet feature?

What I really like myself about TextMate is the infrastructure, but there are two things which comes to mind, probably because they both act as enablers:

1. The ability to switch a normal selection to a column selection by tapping the option key once. For me that upgrades column selection from something I occasionally use to something I use dozens of times each day, even with columns that span only two rows.

2. The ability to have a command receive “current scope” as input. For me this exemplifies the abstraction I am pursuing with TextMate: you want a command to uppercase a string? Make the command (tr ‘[a-z]’ ‘[A-Z]’) and set the scope selector to ‘string’, input to ‘current scope’ and output to ‘replace’. While this action is contrived, it illustrates how everything unrelated to the task of ‘uppercasing the current string’ is irrelevant to the command. In all other editors (that I know of) you would have to write code yourself to find the string delimiters, and then you have the problem that these can be defined differently for different languages.

From your profile on the Wiki, you state you have a skepticism regarding the HCI field. Where does your skepticism lie?

Let me start by saying that I think understanding human cognition is very important for good software design. My skepticism about the HCI field comes from the fact that it is often hard to quantify the quality of results because a lot is subjective and subject for interpretation.

At one point I was semi-employed by a Ph.D. student (of HCI) which wanted me to log all sorts of data so that he could look for patterns afterwards. This is fine in some situations, I have just seen too much of it, and too little aggregated theory, instead there is a lot of common sense and a few authors making a fortune writing about it.

Do you plan to release TextMate as open source? If not, what’s your exit strategy, if any?

I am extremely torn on this issue. I have a lot of things I want to see happen with TextMate and there really is too much for me to do this all alone.

So one option is to hire programmers and basically build a company. Is this something I want to do? Maybe, but running a company requires a steady cash flow. Hiring good programmers can be difficult, and hiring a bad programmer can turn out to be worse than not hire anyone at all, but you will rarely know in advance.

It also requires me to spend time communicating my ideas and do a bit of micromanagement as I probably can’t just hire five programmers and say “make TextMate better” and expect them to know what that means.

On the other hand, the current model (where I do all the work) is not really working as in, it does not scale, and already I have people to help me out, not just for bundles but e.g. while I am on vacation I have other people handle support etc.

So the company slowly becomes a necessity. But you asked about open source, open source I have considered for a few reasons:

1) TextMate already has open source components and it occasionally bugs me that I can’t just point users at the source.

2) I said above that I don’t want to micromanage. When I delegate a job, I expect something specific and if I do not get that I might sometimes be a little disappointed. With open source I am not asking for anything, meaning I will get things I did not ask for, thus I will probably be positively surprised, and the things I may get, will sometimes be things which never occurred to me, thus even with infinite resources, I would not have asked for it (look at Microsoft, they have the closest you get to that, and they do not know what to ask for, so they do not get it, and thus have software which is bad and/or imitations of other products).

So what is stopping me from open sourcing TextMate? Basically two things:

1) if TextMate is open source, can I make any money?

2) if TextMate is open source, will people actually contribute?

Going the company route does not present these problems and I would be able to ensure that TextMate becomes what I have in mind.

Presently I am thinking of both things as possible scenarios, and I am consciously moving toward a modularized architecture that will allow me to test these things in a smaller scale. For example, making some modules open source while hiring people to work on other modules.

Do you have a feature roadmap and, if so, what are your big ticket features of the next six months?

As I mentioned above, the stuff which I get the most excited about myself is the infrastructure.

Things in TextMate are generally triggered when the user does some form of interaction. For example, pressing a key, dragging a file to the edit area, or typing a keyword followed by tab and then based on the structural context (e.g. are we inside a string in a source file?) which TextMate knows about from having parsed the document, some action will fire, like running a command or inserting a snippet.

This simple system has allowed a plethora of cleverness in the form of bundle items, and TextMate 2.0 (though the ETA is not within the next six months) will make the parser able to work with more complex document types, have scope selectors select more than just the structural context, have commands fire for more than just file dropping, key equivalents, and tab triggers.

These improvements to the existing infrastructure will allow for a lot of cool new things. I am deliberately being a little vague on what exactly they are since people have started to copy my ideas, which I have nothing against, I just want to be the first with the implementation.

The design of TextMate is one where you discover what you need rather than features being shoved down your throat. Isn’t there a risk here that a good feature might never be found?

Certainly. One of the reasons I do the screencasts is to educate users of features which might not be easily discovered.

But I don’t think it is a problem that users do not find specific (cool) features unless the feature they do not find is fundamental, like opening files, or something they miss and have spent more than 20 seconds looking for.

I do consider how features can be made more visible, but if you enumerate the features in TextMate there is probably around a thousand, depending on what you count, and most users would be hit by information overflow if all features had an equally prominent visibility.

Ninety Days

When you accept a new job, you don’t know who you are going to work with, what you are going to be doing, and how much (or little) you’re going to like it. Call everyone you want. Ask their opinions. Trust the fact that a good friend referred you for the gig. Revel in the idea that the company has a good pedigree, but don’t delude yourself that in a smattering of interview hours that you’re going to have anything more than a vague hint of your new life.

Try this. Tell me about your best friend. Give me a bulleted list of five noteworthy things you think I should know about your best friend. Got it? Read it out loud. Does this do justice to your best friend? I hear you when you say, “He’d do anything for me”, but why is that? Why is he protective of you? What’s the story behind the bullet? That’s what I want to know.

Each person in your new team has a story they want to tell you and it’s never a bulleted list. Some are going to freely give this story whereas others will carefully protect the fact they even have a story, but until each person you need to work with has shared this story with you (and vice versa), the interview isn’t over. The jury is out and you won’t know if this new job that you’ve begun is actually your job.

Deliberation

Your first job is to relax. Like the first day of school, you’re going to overcompensate in your first day, your first week. Most people do not lay their clothes out the night before they go to work. You’re doing this to calm yourself. Those clothes neatly laid out at the end of your bed are a visual reminder that you have control over this thing that you can’t control.

Relax. There’s an industry standard regarding the amount of time it takes to make a hire and it’s ninety days. New managers hate when I tell them this because they’re so giddy they’ve got a new requisition and BOY WATCH HOW FAST I CAN HIRE. Yes, yes. I appreciate your velocity, but I’m not going to worry about your hire for ninety days.

This chunk of time applies to your new job as well. You’ve got ninety days — three months — to finish your job interview. Draw an a X on a calendar ninety days from now. Make it a physical act that reminds you to relax and to listen rather than fret about what you don’t know. The new team isn’t going to trust you until you stop laying out your clothes, until you stop being deliberate.

I know you’ve done this before: you’ve had five other jobs and you have well refined people assessment instincts. Except, well, they’re biased. These instincts are based on where you’ve been and you have never been here before. My suggestion is that the less you trust your instincts, the more you’ll learn about your new job and that’s why I wrote you a ninety days list:

#1) Stay late. Show up early. You need a map of the people you work with and I find the best way to start scribbling this map is to understand people and their relation to the day. When do they get there? How long until they engage in what they do? Coffee run? Wait, no. Late arriver. Doesn’t leave until he gets something done. Makes his coffee run at 4:30pm. Doesn’t drink coffee? Really? Why? These long days of watching give you insight and they give you tools for understanding what each of your team members want.

#2) Accept every lunch invitation you get. People are stretching themselves for you the first few weeks you show up. They’re going to go out of their way to include you and no matter who they are, you’ve got to take the time to reciprocate. The lunch invite from that guy in the group you pretty sure you’ll never interact with will result in stories and you have a stunning lack of stories right now.

#3) Always ask about acronyms. It’s great that we’re all speaking English, but why is it that you’re sitting in your first staff meeting and not understanding a word? It’s because every team develops acronyms, metaphors, and clever ways to describing their uniqueness which you must understand. Cracking the language nut is absolutely essential to assessing the hand you’ve been dealt and you’re going to need to ask a couple of times.

#4) Say something really stupid. Good news, you’re going to do this whether it’s on this list or not. I’m saying it’s ok. This stupid thing that you’re going to say is going to demonstrate your nascent engagement in your job and when they stop giggling, the team is going to know you’re desperately trying to figure it all out.

#5) Have a drink. Similar to the lunch task, but more valuable. No barrier is crossed when someone invites you to lunch, but when you get the drink invite, someone is saying, “C’mon. Let’s go try a different version of honesty.” Stories are revealed over drinks, not lunch.

Warning: the next three on the list are at the bottom for a reason. These are advanced moves that you don’t want to attempt until you’ve built some confidence that if they go horribly wrong, you have some confidence that you won’t permanently damage your still developing reputation. Read on.

#6) Tell someone what to do. Everything above this list is about listening and this task involves you saying something. More importantly, it involves you telling someone what to do. I don’t know who you are telling or what you’re saying, but the goal is to exert your influence, to test your influence. More importantly, to test your knowledge of the organization and see if this thing you have to say is true. Telling is the sound of your instincts aligning to this particular organization and this thing you are saying is your first bit of inspiration. Trust it. Tell the right person and realize that everyone was waiting for you to say it.

#7) Have an argument. This is the riskiest item on the list, but potentially the most revealing. There’s a good chance when you pull a #6 that this is going to happen anyway. Again, what you are willing to argue about and who is going to be on the other side of the argument is a function of your situation. What you want to understand is how does the organization value conflict? Is it ok that you’re digging your heels in? Do others engage in the argument? Who swoops in to save the day? Can these people argue without losing their shit? Does this team argue out in the open or do they use devious passive aggressive subtlety?

You’re going to learn two valuable things during this professional battle. First, how does this group of people make a decision? Second, you’re going to have a better taste of their passion and their velocity.

#8) Find your inner circle. In your arguments, lunches, drinks, and late nights, you’re going to find kindred spirits. This is the short list of people who share your instincts. These are the ones who complete your sentences and they know your stories. These are the ones who welcome the argument because they know great decisions are made by many. Your inner circle is not exclusive because you’ll go nowhere drawing relationship boundaries among the team. This is the list of people with whom you share your raw inspiration and your stories because you know they’ll gleefully help refine them.

The discovery of your inner circle won’t happen until time has passed. You’ll instinctively be attracted to people who feel comfortable, who feel right, but they can’t be in the inner circle until they’ve passed the test of time. They’ve got to pass through the ninety day list a few times before you’ve heard enough stories to let them in.

Finishing the Interview

It’s not just that you forgot to ask key questions during your initial interview process; it’s that the person that you were walking into that interview isn’t who you are. You’re a resume, you’re a referral, and you’re a reputation.

Your job interview isn’t over until you’ve asked all the questions and heard all of the stories.

Your job interview isn’t over until you understand the unique structure that has formed around this particular group of people. It’s not just the organizational chart, it’s the intricate personalities which have settled into a comfortable, complex, communication structure.

Your job interview isn’t over until you have a framework for how you are going interact with these people and that means understanding not only their goals, but also their invaluable personal quirks. What they tell you the first week has more to do with the fact that you’re new than what they actually feel. What they tell you after ninety days is the truth.

Your job interview isn’t over until you’ve changed to become part of a new team.

Happy New Year.

Bright, Patient Design

The creation of a Rands article goes like this. First, the idea strikes me at some random part of the day… usually in the car to or from work. I spend anywhere from a day to a month fine-tuning this idea in my head until it’s something I want to start writing about. It’s entirely possible that some great work never makes it past this stage because I don’t write it down, but my thought is, “If the idea can’t escape my head, it’s not ready yet.”

When I’m ready to start typing, I fire up TextEdit for a first draft. Yes, TextEdit. I don’t need much out of an editor for that part of the writing process. Actually, all I need is a pleasant font and bold. Code editors don’t work because they don’t have rich text formatting and I use this formatting to visually mark sections and cordon off ideas. Word doesn’t work here because it’s a cluttery mess of functionality I don’t need.

Once I’ve got something 75% of the way there, I start sending it out for content review and copy editing. (If you want to help with Rands stuff, drop me a line. Let’s talk.) This is another advantage of TextEdit — it’s Mail friendly — it pastes exactly what I typed in formatted into the message as opposed to Word which has a penchant to make fonts huge and retarded.

With feedback in hand from the various Rands support folks, I clumsily merge this feedback into TextEdit and then print out the piece and shove it under my pillow for a day. This is bake time. I gotta forget about the piece for 24 hours so I can read it again with fresh eyes before the last edit. There’s a moderately large pile of work which never makes it pass this stage, either; the thought is the same as above, “Not done”.

With a fully baked piece in hand, I begin the mechanical process of prepping the article for posting. Now I need an editor that is markup-friendly. I’ve been using BBEdit since my move to Mac OS X and my thoughts from 2004 still apply: “It’s a fine editor, but what’s the fuss about? Where’s my holy shit?”

I’m not a power user, but I know what I expect out of a good editor and, well, BBEdit is a good editor, but whenever I fire it up I feel like I forgot to read some imaginary manual called, “BBEdit Rocks. Really.” I suspect the fact that I didn’t grow up with BBEdit is part of the issue. The fact that I’m a pure Mac OS X guy with zero pre-Mac OS X experience probably contributes to feeling like I’m missing part of the BBEdit joke. Yeah, Zap Gremlins. Ha ha. I get it. Clever, but great design?

My BBEdit ambivalence allows me to check out new editors as they stream across my consciousness and, to BBEdit’s credit, it’s lasted four years. I’ve test driven several editors during that time and BBEdit remained my technical tool of choice, but it was only a matter of time until someone else knocked my socks off.

The buzz around TextMate started many months ago, but it’s when folks started to ask me to order it that I started to pay attention. There is no copy protection known to man that any bright engineer can’t circumvent, so when an engineer asks you to purchase the software they’re saying, “This is the shit. We should pay these guys for this fine piece of work.”

You bet I downloaded it.

After two steady months of TextMate, I’m happy to declare it my editor of choice because it demonstrates a design philosophy I love. Bright, Patient Design. I’ll explain.

A well-designed application gently lets you know it’s smarter than you. It goes like this:

TextMate: “Hi Rands, I’m TextMate.”

Rands: “Quiet, you, I’ve got stuff to do and no time to do it. I don’t have time to learn a whole crap load of keyboard commands. I’m just trying to format some HTML. Please stay out of my way.”

TextMate: “You bet. Just holler if you need anything.” [insert silence]

TextMate’s interface is a big huge empty space. No toolbar, a clean menu structure. You just start doing whatever it is you do and then, eventually, you need something.

Rands: “TextMate, I need to create a link and IF YOU’RE GOING TO PUT ME THROUGH HOOPS WE’RE THROUGH. I MEAN IT.”

TextMate: “Sure, see that status bar at the bottom, all the HTML commands are there.”

Rands: “Great, now shut up.”

TextMate: “You bet.”

Exploring the status bar at the bottom of each TextMate window is your first glimpse into Bright Patient Design. In a single status bar, TextMate’s potential explodes. First, there’s a exhaustive list of all the different language types supported by TextMate along with a set of formatting and template commands for each and every language. But wait a tick…

Rands: “Hey, TextMate.”

TextMate: “Yo.”

Rands: “I need to add a link.”

TextMate: “Did you check out that status bar?”

Rands: “Yeah, it’s CTRL-SHIFT-L, but I need to associate it with this URL I just put on clipboard. How do…”

TextMate: “Rands, did you use the command?”

Rands: “No, but do I need to paste the HTML and then paste…”

TextMate: “Use the damned command.”

So I do. Ctrl-Shift-L and TextMate does exactly what it’s supposed to do. It adds the HREF and it automagically pastes the URL on my clipboard into the HREF. In my book, TextMate has just taken two separate tasks and made them one. Folks, that’s a 50% savings and 50% savings is engineering nirvana. Careers are made on 50% savings.

Now, I bet BBEdit does this, but fact of the matter is, I don’t know that it does. I’ve spent four years stumbling around that program and my impression is not Bright, Patient Design, it’s Historical Cruft. BBEdit’s biggest flaw is one of its greatest assets: its history. BBEdit’s design is an amalgam of every design decision the Bare Bones Software team has made since its release for System Software 6 in the early 90s and it shows. Go click on the anchor button in the HTML toolbar and tell me what happens. That’s right, you get a dialog with every possible anchor attribute you’d ever need. That’s not bright, that’s lazy.

Bright, Patient Design is knowing that you are going to need to tell people what they want, but having the patience to know they need to discover they need it. It is choosing to stay out of their way while they make this discovery and then, when they’re ready to learn, showing them you can make their life better.

Bright Patient Design acknowledges you are going to make big decisions for your users. You are not going to present every possible bell and whistle. You are going to give them the one bell they need and you’re going to ring it sweetly and they’re going to realize that you’re a better bell ringer than they are.

After my link moment with TextMate, I realized that higher powers were present and I dug into the program. Of course every single damned command, macro, template, and snippet is a customizable script. Of course, it’s trivial to start using these scripts, but TextMate doesn’t throw this seemingly limitless customization in my face, they focus on staying out of the way while I learn at my own pace.

It’s harder than it sounds. Each time Microsoft Excel barks at me asking, “Hey Rands, it looks like you’re managing a list. BOY CAN I HELP YOU!” I want punch my flat panel monitor flat. Excel, you’re not being helpful, you’re being an arrogant prick and shoving your design down my throat. I’ve had the same reaction to just about every Wizard I’ve ever met. Wizards are a grimly unsatisfying experience where potential functionality is dangled in front of me, but I rarely end up with what I need.

Yes, I want you to decide for me, but you better make the right decision based on my need or we’re going have an even bigger problem. Again, this is really hard. Developers have to enumerate every possible user need for their application and then prioritize which of those needs are most important and how to meet them. My guess is TextMate’s developers are a collection of hardcore developers who have been using editors for a bazillion years. In those bazillion years, they got all the market research they needed. They also probably stared at BBEdit a good long time and said, “We can trim 50% of this functional crap and still have a better product.”

Yes, there is a well-defined need for applications where every single option is presented to the user. Photoshop comes to mind. Any professional application, really. You don’t need to be Bright or Patient here in your design because your users are incented to figure out how to be experts. Me, I’m in a hurry and the more your design stays out of my way and let’s me get stuff done, the happier I am and the more likely I’m going to become an expert.

Desktop Accessories

On the list of things I do a lot, typing is up there close to breathing. It started with the Apple II forever ago and now it’s now and I’m still typing every single day and each day I wait for the sharp pains to start racing up my forearms My only guess that I haven’t been afflicted with carpel tunnel or some other repetitive stress injury is that I’m either genetically predisposed not get it or I’m not repetitively injuring myself.

My guess is the latter. I don’t think whatever genes prevent repetitive stress injury have had the necessary time to bake. You’ll have check-out my great-great-great-great grandson who will either sport these evolved RSI-friendly genes or a plug in the back of his head. Depends who wins.

A repetitive injury-free lifestyle involves adjustments to habits and environment. The single best habit you can have is a short attention span. Nothing is repetitive when you can’t focus. You think I’m joking and I kind’a am, but my understanding is that much of the RSI issue is that you stay in the same position for long periods of time where the muscles keeping you in said position get angry. This paragraph is five sentences long and I’ve changed position twice.

If you don’t have NADD, well, then you can change your environment and your environment is your desk. Here’s are my favorite desk accessories:

First, the Big Three. Monitor, keyboard, and mouse. Let’s straighten one thing out first. Any tool which is physically betweteen you and your content is worth investing in. Stop worrying about your processor speed or your front-side bus. Focus on nailing the big three, starting with:

Monitor. I’ve been here. A couple of times. Your monitors are your eyes to your content and if you aren’t spending dollars here to get two flat panel monitors then you’re spending your time organizing your content, not surfing it.

Keyboard. I used to be fussy about my keyboard. I’d swear by the Microsoft Natural keyboard, but I’ve been on Apple’s standard keyboard for many years and I don’t have any complaints. Keyboard characteristics that I care about are feel and sound which, oddly, intersect quite a bit. A semi-padded “click” is what I want to feel and hear when I hit the letter R. Too clicky, too hard, or too deep a push and I’m no longer thinking about what I’m writing, I’m thinking how annoying my keyboard has become.

Mouse. Two essentials here. Wireless and shape. I’m using a Microsoft Wireless mouse, which is a mouthful, but it feels natural in my hand. I can’t live without a right click and a scroll wheel and the mouse has both… and a bunch more buttons that I never use.

Regarding Wireless. A good measure of any tool is the average number of times a week you pick it up and throw it across the room. My average for wired mice was once a month. See, your wired mouse doesn’t stay in one region on your desk. It wanders depending on how your sitting in your chair, your posture, and how much coffee you’ve had. Each time I was sitting in odd position on a caffeine induced writing episode, my wired mouse would find that region on the desk that was inaccessible via a wired mouse. I wouldn’t notice that subtle tug the first three times I tried to drag the mouse to the unreachable… or would I? The fourth time I’d yank the thing out of it’s USB and sling it across the room. It’s one thing to have your significant other interrupt The Zone, it’s a other thing to have poorly designed non-sentient piece of crap get in the way.

Speakers or Headphones? I’ve got both and I use them depending on what I’m doing. Right now, I’m cranking Local H and sitting at my desk with my wireless headphones and a terrific glass of Pinot from Nicholson Ranch. If you walked in my office, my headphones are a handy visual clue, “Don’t bother me”. If I’m doing the same thing with speakers, I’m not in the Zone, I’m just filling time. Wireless is also essential for headphones. I’m using Sennheiser’s right now and I’m going to give them a solid B mostly because I’m so happy about not having to replace the busted headphones I kept tossing across the room. With wireless, I still need to fuss with various controls from time to time, but they work perfectly 90% of the time and they never get wrapped around my chair.

Huge Stack of Paper. Do this right now. Go walk to the closest laser printer and grab a healthy stack of paper and plop on a non-intrusive corner of your desk. Why? Because you sometimes need to write things down on paper. I know you’ve got to-do tracking application or maybe you’re using your mail application to get things done. In both cases, you still need paper. The act of writing down a something on a piece of paper gives that something more reality and if you haven’t a clue what I’m talking about, well, all the more reason to pilfer some paper. Don’t worry, we’ll make more.

Wander Spots. My desks at work and home have visually interesting places to take mental breaks. A stack of books, a photo… any sort of nerd knick knack that feeds your brain. This is where you stop to reflect on the last thirty seconds of your life. How am I doing? Is this feeling right? Maybe I should take another sip of wine. Ok. Back to work. These frequent mental breaks may sound like a lot of work, but these micro-breaks may very well be the reason I’m not wearing braces on my wrists. I stop. I wander. And I return to what I was doing. Sometimes.

Direction. I’ve been flip-flopping on this for years. Do you face the people who walk in your office or do you show them your back? The argument for the back is that anyone who wants to invade your space not only needs to come into your office, they also need to ask for your attention. My theory is that some small percentage of folks will spend the eighth of a second between when they walk in my office and when they ask for my attention asking themselves, “Do I really need his attention? He looks busy.” If the answer is “No”, we both save time. Whether this is true or not, I recently returned to facing my door because folks were scaring the shit out of me walking in my door, sitting down, and then asking for my attention. WHO IN THE. WELL HI.

Since my return to facing the door, I’ve realized that, as a manager, you’ve gotta face the door. That eighth of a second between when you see someone walk in the door and they say something is invaluable. Are they pissed? Is this important? Are they confused? What hat do I need to wear? All of this analysis goes down before anyone says a thing and that analysis prepares me for whatever has just walked into my space.

Trickle Theory

Buried.

Back at the start-up, we were shifting gears. After six months of talking about shipping a product, we needed to ship a product and nothing gets everyone’s attention like a deadline. The good news was that QA had been doing its job and there was a pile of work in our bug database. The bad news was that no one had looked at the database in months.

We had a Rent-a-VP at the time, and as temporary executives go, he was sharp. He quickly deduced our goal — “Ship a Quality Beta” — but he also quickly discerned that we had no idea about the quality of the product because of our pile of untriaged bugs.

He called a meeting with me, the QA manager, and the tech support manager. His advice: “Triage every single bug in this fashion and tell me how many bugs we’ve got to fix in order to ship this Beta.” And then he left.

Every single bug. 537 bugs. You gotta read the bug, possibly reproduce it, and then make an educated team decision. Let’s assume an average of five minutes per and you’re talking about… crap… 45 hours of bug triage. It’s an impossible task. I’ve got features to fix, people to manage, and I haven’t seen the sun on a Saturday in two weeks.

Let’s take a brief segue and talk about the huge value that exists in a bug database. In just about every company I’ve worked at, the only source of measurable truth regarding the product is the bug database. Marketing documents get stale. Test plans become decrepit. Test case databases slowly mutate into the unusable personal to do list of QA. The bug database is the only source of data regarding your product.

I know this. I know that once I’ve effectively scrubbed the bug database, I’ve got the single most informed opinion regarding the product.

But.

537 unscrubbed bugs? 40+ hours of bug drudgery?

Please. I’ve got a product to ship.

My normal approach when faced with an impossible task is analysis because analysis gives you data, which in turn allows you to make a confident decision. So, I do what I did above: carefully estimate how long it will take to complete… 5 minutes x 537 = impossible. This fair estimate freezes me with fear. How in the world am I going to get my other five jobs done whilst scrubbing 40 hours of bugs? Once I’m good and lost in that fear, the impossible task, I’m no longer thinking abut getting the task done, I’m thinking about the fear.

My advice is: START.

“But Rands… I’ve got three hundred tests to run and one day to…”

Stop. Go run one test. Now.

“Wait, wait, wait. Rands. Listen. They need this spec tomorrow @ 9am…”

Shush. Quiet. Go write. Just a paragraph. Now.

Welcome to Trickle Theory.

Our Villain

My traditional first move when managing impossible tasks is to put the task on a to-do list.

“There! It’s on the list. AaAaaaaaah… didn’t that feel good? It’s on the to-do list, which must mean it will be done at some point, right?” Wrong. Putting the task on the to-do list does one thing: it avoids The Critic.

Every story needs a villain and in this piece our villain is The Critic. This is your internal voice which does careful and critical analysis of your life and he’s gained a powerful place in your head because he’s saved your butt more than once.

He’s the one who told you that offer from the start-up smelled too good to be true. You remember that company, right? The one that simply vanished three months after you declined that stunning offer letter. It was The Critic who said, “How in the world can they afford to give anyone this type of offer when I don’t even understand their business model?”

The Critic was the one who calmed you inner nerd and convinced you to not buy HDTV three years ago and he told you not to trust that fast talking engineering manager who emphatically guaranteed his team would be done on schedule. The Critic said, “People who talk fast are moving quickly to cover up the gaps in their knowledge.”

The Critic was right. The Critic gained credibility, but for this piece, he’s still the villain.

I know it feels great to get that impossible task on the to-do list. I know it feels like you actually did something, but what you’ve done is avoid conflict. You know that if you start considering the impossible task, The Critic is going to chime in with his booming voice of practicality, “RANDS, what are you THINKING? NO ONE ADDS FEATURES TWO WEEKS BEFORE A SHIP DATE!”

“Ok, alright, you’re right, but the boss wants it and when the boss gets something in his head it takes a lot of work to blah blah blah…” Now, you’re justifying, you’re worrying, and you’re arguing with The Critic when what you should be doing is starting.

Nothing Happens Until You Start

Let’s first break down impossibleness. For the sake of this article, there are two types of impossible tasks. First, there are impossibly dull tasks. This is work which requires no mental effort, but is vast in size. Bug scrubbing is a great example of this. At the other end of the spectrum are impossibly hard tasks. These are tasks like, “Hey Rands, we need a new product by Christmas. Yes, I know it’s October. Ready. Go!”

Oddly, attacking both boring and hard tasks involve the same mental kung-fu where your first move is starting.

Such silly, trivial advice… start. Still, take a moment and examine your mental to-do list or just look at your written one. How many terribly important tasks have been there more than a month? More than a year? Embarrassing, huh? It’s not that they’re not important; it’s just that you didn’t begin and you didn’t begin because the moment you think about starting, The Critic weighs in, “How will even start? You’ll never finish! You don’ t even know where to start.”

Begin. Go read the first bug. Don’t think about how many are left. Go to the next one and watch what happens. In just a few minutes, you’ll have made something resembling progress. Two more bugs and it’ll start to feel like momentum. Progress + momentum = confidence. The moment you see yourself tackle the smallest part of the impossible task, the quieter The Critic becomes because you’re slowly proving him wrong.

Iterate

The second piece of advice is simpler than the first, which is hard to imagine. Iterate. Once you’ve kicked yourself out of stop, iterate becomes a little easier, but if you’re truly tackling an impossible task, The Critic simply isn’t going to shut up.

“Wow, you’ve closed five bugs… Only 532 more to go, sport!”

Iteration and repetition aren’t going to silence The Critic. Progress will. A beautiful thing happens when you point your brain at an impossible task. Once you’ve begun and start chewing on whatever the task is, you’ll start to see inefficiencies and begin to fine-tune your process. This is how an engineer who tells you, “It’s going to take two weeks to write that code” comes back after the weekend and says, “It’s done”. He honestly believed that it was a two week task, but as soon as he started chewing on the problem, he realized he’d written similar code a year ago, which, with a half a Saturday of tweaking, provided the same functionality.

The same applies to small, duller impossible tasks. Above where I estimated it’d take 5 minutes of triage for each bug, I didn’t take into consideration that after about 50 bugs, I was going to be really good at scrubbing bugs. I’d start to identify people who generally wrote good bugs versus those who didn’t have a clue. I’d learn the problematic areas of the product and learn where I could make snap judgments regarding bug viability. What was a five-minute triage window for the first 50 bugs was one minute for the next 50 and that turned into an average of 15 seconds per bug for the second hundred when I really got rolling.

This means that my original estimate of needing 45 hours for bug scrubbage turned out to be roughly 7 hours. What I thought would take a week is actually going to take one solid day.

Do not believe that this gives you the authority to slice every single estimate by 5. Turns out that impossible tasks, upon consideration, actually are terrifically hard. Believe this; an individual tends to be very bad at work estimates until they’ve begun the work.

Mix-it-Up

Crap. You’ve been saddled with an impossible task and after a weekend of no sleep you have confirmed, yes, the task is impossible. In fact, you’ve started, you’ve iterated, and you still have no clue how to actually complete the task. Story time.

This spring I had a crew come up to clear some brush on the property. Now, the property is a pleasant combination of oaks, bays, and redwoods, but much of it had become overgrown and inaccessible. My first thought when I moved in was, “Hell yes, I’ve got clearing mojo!” My thought after one weekend of clearing, when I was partially successful at clearing up 50 square feet of 5 ACRES OF FOREST was, “Impossibly boring”.

This attitude gave me a unique curiosity when the crew of three men showed up, chain-saws in hand, to clear the land. They had no issue starting and they clearly had the iteration thing down, but they also demonstrated the last and most component to Trickle Theory: mix-it-up.

It went like this: one guy would cut and drag brush into the fire, another would cut trees down, and the third would trim fallen trees. This went on for a while and then they’d all switch. Now, drag guy was cut guy, cut guy was hauling wood guy and trim guy was stack guy. During lunch, I sat down and asked, “When do you guys switch jobs?”

“When we’re bored.”

Beautiful, beautiful Trickle Theory. How cool is this? If you’re working on an impossibly hard or impossibly dull task and you find yourself mentally blocked by boredom or confusion, stop and do something else. The benefits of stopping are stunning.

First, stopping smacks The Critic squarely across the face. See, he’s also the voice in your head saying, “Uh, if we don’t work hard on this, we’re screwed”. And the longer you sit there grinding out the impossible task when you don’t want to, the louder he gets.

Second, stopping to do something else is fun for you and your brain. It breaks the cycle of whatever tasks you’re doing and points your grey matter at a whole new problem and your brain loves new, it consumes new with vim and vigor, and that puts spring in your proverbial mental step.

Third, and most important, even though you are stopping, your brain is bright enough to keep background processing the impossible task. This is why we find so much inspiration in the shower; you’re stopping and letting your brain wander, and your brain is smart. Your brain knows how important it is to rewrite that feature in two days and your brain is always working on that feature whether you know it or not.

“Wait, wait, wait. Rands, let me get this straight. Your suggestion when I’ve got a looming impossible deadline is to stop working on my deliverables?”

What I’m saying is, when you’re facing an uphill mental battle with yourself regarding the impossible task, it’s time to choose another battle… that isn’t a battle.

Entropy Always Wins

My life appears to be an endless series of tasks which are geared to slightly tidy up my world. Viewed as a whole these tasks represent a lot of work. Viewed against the actual amount of entropy in play in my small part of the world, these tasks represent a futile effort.

Fact is, your world is changing faster than you’ll ever be able to keep up with and you can view that fact from two different perspectives:

1) I believe I can control my world and through an aggressive campaign of task management, personal goals, and a CAN DO attitude, I will succeed in doing the impossible. Go me!

-or-

2) I know there is no controlling the world, but I will fluidly surf the entropy by constantly changing myself.

Surfing entropy takes confidence. This isn’t Tony Robbins confidence, this is a personal confidence you earn by constantly adapting yourself to the impossible.

Russian History

“Rands, I’ve got the idea. I’m serious. It’s going to be big and I’ve got my three MBA buddies lining up seed financing. Seriously big idea here, Rands. And I need a favor.”

Uh oh.

“I need a Free Electron.”

There is a list of the six confirmed Free Electrons that I know. Every six months I rewrite this list on a small yellow sticky to remind myself who these people are while also thinking if there are any new additions to the list. When I’m done, I fold the sticky into a small yellow square and swallow it.

There’s no way I’m coughing up my Free Electron list. I’m saving those six names for the day when The Great Idea finally shows up and I start dialing for Electrons.

Sorry.

I will make it up to you by describing two other essential oddly-named hires you need to make whether you’re at a start-up or a big company and we’ll start with:

The Russian Lit Major

This is a strange hire because one of the defining characteristics of the Russian Lit Major is that they simply aren’t that technical. They aren’t going to write code and when they first show up, your engineers aren’t going to trust them. Still, they are in engineering and they serve an essential function. They translate.

The Russian Lit Major should have been a computer science major, but they got off track. I don’t know how or why, but Russian Lit looked appealing to them as they were slogging it through college. They own a computer and they can do some wondrous things with that computer, but they can also speak Russian and read Tolstoy, which are two things you’re never, ever going to do.

When the Russian Lit Major got out college, they quickly discovered that the market for Russian Lit Major skills were, well, non-existent. They remembered, hey, I’ve got a computer and I’m not scared of it, so maybe there is a gig for me in high tech? I hear the money’s good.

Somehow, who knows how, they got hired in a big high tech company and they cut their teeth. Localization, technical publications, who knows… some Russian Lit Major-friendly portion of a large company where the Russian Lit Major remembers, “Shit, I should have been a computer science major” where it’s clear engineering is the place to be.

This first gig defines two things for your Russian Lit Major. They learn how a high tech company functions and they begin their professional struggle towards software development. It takes years and it probably never happens the same way, but the Russian Lit Major lands in an engineering group. Maybe it’s as program manager position or perhaps it’s a product manager, but they make it to engineering… where no one trusts them.

Trust them. See, in the struggle to get from wherever they started to their eventual engineering gig, the Russian Lit Major networked with a good portion of the company. They learned how different groups worked and they learned how to speak a variety of organizational dialects. Whether they eventually land in an engineering group inside their first company or at your start-up, an experienced Russian Lit Major has developed a complex communication toolkit to relate to the rest of an organization and that’s what your engineering team desperately needs.

If you’re in a start-up, you need them because, very soon you won’t be able to figure out everything by walking the hallway. There are too many people. If you’re in a big company, you need them for the same reason; there is simply not enough time in the day to regularly take the pulse of the company and that is what your Russian Lit Major is going to do. They’re going to make sure that whatever relevant shenanigans are going on outside of your team are going to cross your table. They’re going to eliminate surprises and they’re going to do this the best when they know that they are an essential part of the team.

Your team is not going to trust your Russian Lit Major because in their engineering world, if they don’t write code, they don’t create anything. Therefore, they are a waste of resources which could be better spent buying them a 30” flat panel. Your job, as the engineering manager, is to drill into their head there is exactly one currency in a company and that’s information. They won’t believe you. They think they fact they made file searching in the application 27% faster is a major corporate development and while I’m happy file searching is faster, I’m more interested in whether or not my Sr. VP is going to kill the whole project.

Cruise Director or perhaps Spy is a better name for the Russian Lit Major, but those terms are pejorative. They ignore one simple fact: it’s not that your Russian Lit Major speaks Russian or is even Russian Lit Major. The point is that in their quest to get into engineering, they’ve developed vision. They’ve seen aspects of the organization that you’ll never see and that gives them a uniquely valuable perspective on how to get stuff done.

The Historian

The other essential hire is easier to explain because they are an engineer, but they’re harder to hire because you’re not going to know they’re a Historian until a couple years after the hire. Story time.

We were in the scheduling phase of the third major release of the web application at the start-up and I was lying like a fiend. Now, I didn’t know I was lying because I was passionately waving my hands in front of everyone telling them that, yes, we could hit June. It was only four months away, but we only had two features and the team was 25% bigger, so this is GOING TO BE NO PROBLEM PEOPLE. CHAaaaaaaARRRGE!

Phil in the front row raised his hand and I deflated because I knew whatever Phil was going to say was going to totally derail my impassioned plea.

“Rands, we’ve never done a release in less than six months. Furthermore, with each new customer, the team is doing additional support work that we’ve never integrated into the schedule. Lastly, we’ve got an additional new product that no one is talking about that is going to dominate at least two engineers’ time.”

Phil is a total buzz kill.

No, Phil is a Historian. He never forgets a damned thing.

As a manager, when you’re standing in front of your co-workers, waving your hands, and possibly lying, there are two types of folks in the audience. Those who will let you lie and those who will raise their hands and explain how you are lying. More often that not, that’s your Historian.

That is the basic essential function of your Historian. They have deep organizational memory. When everyone is panicking because the boss says we’ve GOT TO SHIP in three weeks, the Historian looks at the bug database, counts the open bugs, estimates the incoming bug rate, scribbles on his white board and thinks, “We’ll be shipping in six because, historically, this is how many bugs we fix a week and that is how many are still going to be found. Hasn’t changed in four years. End of story.”

A good manager doesn’t actually lie, but often when we get our lips flapping about some important strategic direction, we forget about basic organizational physics. This is when a good Historian chimes in, not with the intent of being contrary; but because they are the conscience of the organization.

When you’re thinking Historian, I want you to think jwz of Netscape fame. He remains one of the defining Historians for me not only because he took the time to write down what was fucked up at Netscape, but he also clearly cared about the health and well being of the “idea” which, through his influence, became Mozilla. To me, that’s the definition of a great Historian. Someone who knows when it’s time to stop boring you with facts and starting reinventing the future.

Yes, Historians can be squeaky and aren’t always right. They’re going to annoy you with their inconvenient truths, but they’re simply trying to keep you honest.

Now Hiring

You don’t actually hire either of these folks. As I said above, Russian Lit Majors are likely to show up as a program management function and who knows whether they even let you interview those types. In any event, once you’ve correctly identified a Russian Lit Major, your job is to bring them as close to the organization as possible. You do this by explaining to all those engineers who say, “Uh, she doesn’t code… why should I listen to her?” that “You should listen to her because she knows more about this company than I do”.

You don’t hire Historians, either. You hire great engineers who, after a year of silence, raise their hand during that all-hands when you’re lost in the passion weeds and say, “Rands, you said this a year ago. What’s changed since then?”

“Uh. I did? Really? How’d it sound back then?”

Joe

Actual conversation.

DSL has been off for over 12 hours and that’s about my limit. There’s only so long I can do without a fresh set of bits, so I break down and do my third least favorite thing to do… call customer support.

Customer support frustrates me because of the well-designed ability to do nothing. This is intentional. The support process is designed to filter out the idiots which means if you want to actually find a living breathing human being, you must subject yourself to a series of idiot tests. This is why I reserve customer support excursions for dire situations. No DSL for half a day is dire. Let’s go.

My first ten minutes on the phone are spent in admiration for how far voice recognition has come. First off, it’s working 95% of the time, which is significant. I’ve been making fun of voice recognition for the better part of a decade, so seeing it applied in a real-time business situation is cool. Also, my DSL provider has done something smart with the recordings which guide me along. The recordings use common language… sometimes slang. For example:

VOICE ON PHONE: If you’re looking for information about new DSL service, say “New”. If you’re having problems with your existing DSL line, say “Problem”.

ME: Problem.

VOICE ON PHONE: Got it.

Got it? That’s slick. This use of relaxed language gives me the impression I’m dealing with less of a corporate monolith, but we’re just getting started.

My call proceeds via the automated customer support center and I figure out there’s an outage in Sacramento that “could” apply to me. Problem is, Sacramento is 100+ miles away from Randsville and that’s far enough for me to push a little harder, so I do it… I say, “Operator”.

Here’s the transcript:

REAL VOICE ON PHONE: “Hi, thank you for calling SBC. My name is [pause] Joe. How many I help you?”

Now, I’m always terribly nice to customer support folks. Even though I’ve just spent 30 minutes jumping through idiot hoops to get to them. They’re just doing their job and being kind sometimes helps.

ME: “Joe, hi. My DSL has been offline for 12 hours now and I’d like to get some information about when I might get my DSL back.”

JOE: Let me first start by apologizing on behalf of SBC for this inconvenience. Can I have your DSL account number please?

Joe’s laying it a bit thick, but ok. Whatever.

ME: Sure, it’s ###-#####.

JOE: Thank you. Sir, if may ask, what is your name?

ME: It’s Rands Pantalones.

JOE: Thank you. Sir, if I may ask, may I call you by my first name?

Ok, what the hell? Now, you should’ve guessed this is clearly outsourced customer support. No big news there. It’s also pretty clear that “Joe” is reading from a series of carefully scripted cue cards. Even if his delivery wasn’t so stilted, the content of the questions just scream FOCUS GROUP DERIVED FEEL GOOD CONVERSATION TECHNIQUES. Let’s move on.

We continue. He tells me what I already heard from the automated customer service. There’s an outage, but it’s over 100 miles away and I want to make sure I’m a part of that 100-mile radius, so I push Joe a bit.

ME: Joe, Sacramento is far away. Can you confirm that my outage and the Sacramento outage are the same thing?

JOE: [long pause] Rands, let me again apologize on behalf of SBC for this inconvenience. A moment please. [another long pause] Rands, do you like sports?

RIGHT OK NOW YOU’VE BLOWN IT JOE.

I realize the cue card says, “Choose from one of the following MAKE A CONNECTION WITH THE CUSTOMER questions”, but I’m becoming more comfortable with the thought of dealing with the voice recognition system rather than Joe. It’s not that I believe Joe isn’t a decent human being… he’s just on the other side of the planet and I don’t know shit about cricket and he knows less about ice hockey, so why are we doing this dance?

My discomfort with the Joe experience would be good segue into an incensed rant into the evils of outsourcing, but I don’t want to go there. I’m happy Joe has a job and I’m sorry about whoever lost their job back in the States, but I have one piece of advice for both of you.

Cogs get outsourced.

Key Exports

Last month, I spent an hour explaining to the dean of a local college what kind of curriculum he should be schlepping to the local Silicon Valley kids. His first question was, “What is your hardest technical question?”

Before I answer, a brief aside. Yes, I’ve lost some sleep worrying about the perception that high tech jobs are being shipping over seas. More importantly, I’ve fretted that declining enrollments in computer science programs are direct result of this outsourcing. A decrease in the programming population in the US of A would mean it’d be harder for me to hire a fresh out of college guy/gal to beat up for a few years, but I’ve got some really good news for you.

The next generation already knows more about computers than you do and they haven’t even made it to college yet.

The current generation never knew a home without a computer. They assume they have ready access to just about any piece of information… and they’re probably working on their own Linux distribution right now. As a means of shaping your brain for critical thinking, I’m going to give college two thumbs up. As a requirement for doing great work in the software development industry, I’m going to give a college degree a long “Hmmmmmmm” while I slowly stroke my goatee.

Back to the question, “What is the Rands’ hardest technical question?”

ME: “I don’t ask technical questions.”

Listen, if you’re sitting in my office for an interview, I am assuming you’ve got technical chops. We wouldn’t have let you in the door unless we could figure out from looking at your resume that you had the technical skills to do the job. Doesn’t matter if you’re a college hire or Mr. Lord of the Database. I’m not vetting you for technical ability, I’m vetting you for the breadth of your vision, I measuring your ambition, and I’m looking for a sign that you believe you can change the world. Really. If all you want to be is a cog in the machine, quietly hiding in the 27th floor of the Behemoth Corporation, Inc., well, that’s great, but here’s the deal: cogs get outsourced.

As I’ve already discussed, jobs that can be “well specified” are being shipped offshore. High tech moved manufacturing offshore a long time ago and now we’re in the midst of pushing technical and customer support there. These are jobs which can be described with a flowchart, a specification, a means by which the job can be performed in a reliable and measurable way.

Think about Joe’s job. He’s spending his day following a well-defined routine. These are the calls and this is the flowchart. Joe has a daily metric. Joe, you are successful if you resolve 27 calls per day. More is good. Less is bad. The definition of this metric is why SBC is ok with outsourcing their customer support overseas. They did the math. 27 calls a day in the US is $50.00 and 27 calls overseas is $30.00. Multiply that by 27 million calls they do a year and you’re talking serious bank.

Joe is happy he’s got a gig and so am I, but just because his country provides a better dollar per call ratio doesn’t mean he’s got a guaranteed gig. Watch, two years from now Fezlakistan will burst onto the outsourcing stage and guess how long it’ll take your corporate behemoths to do math and start shipping their cogs there. Sorry, Joe. Keep reading. I can help.

Interfacing with Humans Pays Big Bucks

Well-defined QA and engineering is right on the tail of manufacturing and that’s A-OK with me because nothing that I’ve done in just under two decades of software development has been well-defined.

Seriously. I’m coming up on almost 15 years straight of non-stop development, crunch cycles, and fire drills. I work hard on improving process and quality, but it’s hard to write a good spec when the VP of Engineering is telling you that if we don’t get Customer X that feature, well, 150 people lose their job. So, make the call, don’t sleep for two days to get the product out or write a spec that is going to make QA and Documentation’s job easier?

The process weenies out there are now standing at their desks viciously shaking their finger at the screen as they read this. They are saying, “Rands, you just got lucky. You’ve just been fortunate enough to land at successful companies where these fly by the seat of your pants design shenanigans can exist because the cash is pouring in elsewhere.”

Really? Fifteen years, four companies, and six promotions later… you think I’m winging it? No, I just looking like I’m winging it because I never stop moving.

Seriously, I do not specialize in hardened software that keeps submarines pointed in the right direction. I work on software where the primary user is you, the person who stares at the bleeding edge and thinks, “What’s next?” Predicting this future is a messy business. There is a distinct lack of flowcharts. Practically zero spreadsheets. People argue a lot, but they’re arguing because the best way to refine an idea is to throw it in a mosh pit of creative people, wait, and then see what emerges.

Jobs in this crazy design arena, so far, are safe simply because:

• You can’t outsource creativity.
• You can’t outsource thinking.
• You can’t outsource passion.

Our Peculiar Accent

The number of people needed to create a viable product is decreasing. We need fewer folks who make widgets and more folks who are staring at the entire widget landscape and wondering, “I wonder what happens when I put Widget X near Widget Y… Hmmmmm… I think I’ll call it Flickr.”

I’m not suggesting that it takes any less hard work or collection of bright college brains to get these ideas off the ground, but I do know that within the circles I travel, there is a distinct optimism regarding ideas. Folks believe they can do anything. I love to think this sense of entrepreneurial spirit is an American asset, but that’s absurd.

If we have to outsource something, let’s work on outsourcing that. Let’s show the rest of the planet the excitement Borland felt when it started to go toe-to-toe with Microsoft. Let’s demonstrate the enthusiasm a bunch of midwest college kids felt when they realized this browser thing they wrote was changing the world.

If we have anything to share with the rest of the planet, it’s our own peculiar entrepreneurial accent.

WWDC and SXSW

Two days later and the WWDC hangover is just about gone. I’d like to say the hangover was primarily booze-related, but it was a stress hangover. We had some big things to pitch this year and getting that pitch refined took some work. That is an understatement.

Thanks to everyone who dropped by to say “Howdy” and “We get it”. I appreciated that.

Next on the Rands public speaking schedule is, hopefully, a return to SXSW. The folks at SXSW are taking a different approach with developing content by asking former presenters and panelists to submit ideas and then have the community vote on those ideas.

I’ve got a proposed session under review called “The Design Aesthetic of the Indy Developer” and you should vote for it here:

http://2007.sxsw.com/interactive/panel_picker/

The description: “This panel intends to explore the product lifecycle (or lack thereof) within very small software development shops. The goal is to explore the experiences of successful small developers and discuss the design process. Panelists will represent significantly different platforms and technologies to give a broad set of (hopefully) differing opinions.”

Like last year, I’ll be gathering a pile of notable panelists from differing backgrounds to have it out on stage for everyone else’s entertainment.

Lots of good potential panels on the SXSW2007 docket, check it out…

Still Back from Europe

The week before WWDC is a good time to remember that it won’t always be like this.

Take a deep breath and…

A Nerd in a Cave

The first few days of any significant overseas trip, I’m a jerk. It’s not just the jetlag that’s poisoning my attitude; it’s the lack of context. I get twitchy when I don’t know where my stuff is. Combine that with the fact that no one is speaking English, there are two toilets in the bathroom, and I have no idea what time it is and you can begin to understand why I’m in such a foul mood.

Three days in, I’m sleeping, I know it’s called a bidet, and I’m working hard on my Italian R and U sounds. I’m having fun, but I’m still thinking about my lack of context. I’m thinking about the familiar place I’ve built so that I can work.

The Cave

The picture on the About page is my Cave. It came as part of the new house. I didn’t paint the walls blood red, they came that way. Most folks who get the tour walk into The Cave and gasp at the walls. “They’re so dark how can think surrounded by this ominous redness?” I nod and grin slightly and shuffle them off to the next room. See, I love my Cave. The thick blood red walls wrap me in comfort and that is what a Cave does.

My Cave is my intellectual home. My kitchen is where I eat, my bed is where I sleep, and my Cave is where I think. Everyone has some sort of Cave; just follow them around their house. It might be a garage full of tools or a kitchen full of cookware, but there is a Cave stashed somewhere in the house.

The nerd Cave has some specific traits:

• A computer on a desk with ready access to the Internet. The fact that a computer without an Internet connection is essentially a very expensive DVD player is a recent development, but the fact is, when I sit down at my MacBook and there is no wireless I think, “Well, I could play Bejeweled, right?” In The Cave, the Internet is the life blood. It connects this dark place with the rest of the world.
• World-canceling features such as a door or noise-reducing headphones. These features are a nuisance to significant others interested in communication, but I’ll get to that in a moment.
• A random collection of comforting nerd knick knacks. This varies wildly from nerd to nerd, but there is always at least one object or talisman of nerd-dom sitting in the Cave. I have this white carved stone polar bear staring at me right now. I think I got it for Christmas. It’s been staring at me for ten years now and each time I sit down in the Cave, I worry that if the polar bear wasn’t there… I wouldn’t be able to write.
• Something to drink. This may be my thing, but I can’t really settle into The Cave without something liquid. Right now, it’s a cup of homebrew by Peet’s. In the afternoon, it’s a glass of water. In the evening, it might be wine or a beer. For me, the drink is a mental pause where I intensely scrutinize the last 30 seconds. What did I just write? What am I trying to say? [sip] Ok, back to work.
• A well-defined layout. This ties into my NADD, but I have deep knowledge of the layout of my Cave. Each month, the housecleaners come for a tidying of the house and each month I walk into my office when they are done and spend 30 minutes adjusting my monitors, relocating my pens, and re-piling my papers. I think it’s great that someone is coming to clean the house, but I wish they’d STOP TOUCHING MY STUFF.
• A view. Like the drink, the view is a mental break, an escape to somewhere else that provides a brief alteration to perspective. This is why everyone in the office wants a window. It’s not a status symbol, it’s an escape. I’ve seen nerds without a view go to great lengths to create one. My manager at UCSC built a working window frame in his subterranean office and put posters from around the world behind it. When I left UCSC, he had a poster of Audrey Hepburn from Breakfast at Tiffany’s.

It’s an ominous name: Cave. It alludes to a dark, damp place where you are likely to be eaten by a grue. The irony is that the purpose of a Cave is not to insulate, its purpose is to germinate. I’ll explain.

The Zone

Each weekend morning, my process is this: I wake up, walk up stairs, sit down at the computer, and figure out what is happening on the planet. Once I’m comfortable the sky is not falling, I walk to the kitchen, grind my coffee beans, and begin to boil water. While the water is heating up, I return to my computer and follow up on whatever tidbits tickled my fancy from my first pass. This morning, it was some World Cup research followed by looking into options around wireless headphones. Turns out, Sony sucks. Go figure. Water’s boiling! Back to the kitchen, where I pour hot water into my French press and dig up my favorite ceramic cup. The coffee needs to sit for three minutes, which means back to the computer! Ok, so why do Sony headphones suck? Poor sound quality? Bad design? Bit of both, really. Coffee’s ready, so one more trip to the kitchen where I pour the steaming brew into my favorite cup and travel, once more, to my Cave.

It looks like a lot of work, but I do it instinctively . It’s a routine designed to do one thing — get me into The Zone. Much has been written elsewhere about the mental state that is The Zone, but I will say this: it is a deeply creative space where inspiration is built. Anything which you perceive as beautiful, useful, or fun comes from someone stumbling through The Zone.

Once I’ve successfully traversed my morning routine and have entered The Zone, I am OFF LIMITS. I mean it. Intruding into The Cave and disrupting The Zone is no different than standing up in the middle of the first ever showing of The Empire Strikes Back, jumping up and down, and yelling, “DARTH VADER IS LUKE’S FATHER! DARTH VADER IS LUKE’S FATHER!” Not only are you ruining the mood, you’re killing a major creative work. Think about that the next time you enter The Cave with a useless question about what shoes you should wear.

No, I’m not going to answer the phone. In fact, it’s a sure sign of compromised Cave design if I can even hear the phone ring. And no, I don’t hear you when you walk in and ask if we should go to the park tomorrow. I don’t hear you the second time, either. I don’t mean I’m ignoring you because that’d involve using precious brain cycles I need for The Zone… I really CAN’T hear you. That’s how deep I am in The Zone.

No , I have no idea that it’s been four hours since I closed the door and began furiously typing. Really, the only things I know are: a) when my coffee cup is empty, and b) when I need to head to the bathroom.

Yes. When you successfully penetrate The Zone, there is a chance I’ll be an asshole. In fact, I might snap.

The Snap

This is where I apologize.

No one deserves to be on the receiving end of The Snap. All you were really doing was coming in to see when I was done because we agreed we’d go surfing this afternoon. Still, I got in The Zone and I’m writing this wicked article and WHO ARE YOU AND WHAT DO YOU WANT? The Snap is a glare, a raised voice… something designed to indicate you are PISSING ME OFF with your presence.

It’s not fair, I realize that, but think of it like this. If you walk up to me and slap me across the face, I’m not going to think, “Why’d you do that?” I’m not going to take the time to dissect the situation. My instinct is going to be pure, primal, and immediate. I’m going to slap you back.

The reason for this irrational reaction is antiquated brain wiring. Four million years ago it was to my evolutionary advantage to respond to slaps as quickly as possible because they were often precursors to being eaten. Rather than piping my slap response through the “What is a Reasonable Response?” portion of my brain, it’s wired straight into my “React Immediately or Else” area. Somehow, The Snap response has the same wiring. Invasion of The Zone is akin to some primal activity that required the brain to wire itself for immediate, irrational response.

It’s not right, it’s not socially acceptable, and I regret my actions 30 seconds later, but in 20 years of nerdery, the quest hasn’t been to kill The Snap, but figure out how to manage it.

The Place

Try as I might, I don’t always make it to The Zone. I’ll go through all my odd little pre-Zone activities of drink and music selection. I’ll slightly adjust the five essential objects on my desk and I’ll begin… playing World of Warcraft.

This is not The Zone… this is The Place. It is very similar to The Zone in appearance, but, mentally, it’s a different muscle that I’m exercising. If The Zone is akin to playing power forward in a championship hockey game, The Place is the six hours spent in the weight room the day before. Yes, I’m using my mental muscles, but I’m not really building anything.

The rule is this: your significant other can interrupt The Place with impunity. That’s the rule. I might Snap, but if you let me linger in The Place like you should let me work in The Zone, you’ll never see me. If you walk into my office to ask me something and see a half-naked night elf dancing on my screen, you are hereby authorized to invade. Mistakes will happen and you’ll invade The Zone thinking it’s The Place, but after I’ve cooled down, it’s my responsibility to explain why what looks like The Place is actually The Zone.

Other Places

Nerds are rewarded for structure. We get big bucks for reliably generating useful technology that works. Sure, we’re artists, but it’s an art of patterns, repetition, structure, and efficiency (I swear, it’s sexy). This makes it not surprising that the places we create in our homes and in our minds are designed in the same fashion.

The risk with these places is the same risk with all comfortable places. In the comfort, we forget that some of the most interesting stuff happens elsewhere.

The Forums

Some of my earliest memories of hanging with the Dad were visits to the local hardware story, Orchard Supply Hardware. I remember two things. First, the distinctive smell, which I learned, years later, is the stench of fertilizer. Second, the huge amount of time it actually took to get to the register, which was near my primary target, the candy.

The Dad was smart. He knew I’d come because he’d always buy me a treat, but at came with a cost. The Dad was physically incapable of spending less than an hour in Orchard Supply and WE WERE THERE FOR A BOX OF NAILS. He had to soak in the place, wander each aisle, muttering to himself… it drove me nuts. By the time I was a teenager, I was a tremendous jerk, hated my parents, and swore to never go to a hardware store again. THERE’S CANDY ELSEWHERE, POP.

During the carefree apartment rental years, I avoided hardware stores by purchasing the inevitable hammer at the local grocery store. My hardware policy changed the moment I bought a house, when WHAM I needed a wheelbarrow, and it turns out they don’t sell wheelbarrows at Safeway. It was time to return to Orchard Supply.

The place smelled the same. All fertilizery. Same folks wandering around in their forest green vests trying to look helpful. Same horrible fluorescent lighting. I wondered if they candy selection has improved in the past decade? Hey, what’s this? A tool chest. I need a tool chest. Wait, this vice grip rocks. I could totally fix my kitchen with this thing. And that reminds me… I’ve got that loose tile… Where is the tile glue? I NEED A HELPFUL GREEN VEST STAT!

The cliche about hardware stores and people over thirty is this: it’s a toy store. We go there to buy crap that looks cool, but that we don’t really need. Wrong. My Dad was not wandering Orchard Supply looking for crap; my Dad was looking for ideas. That’s what a great tool does: it inspires you to build.

Rands in Repose Forums

I’ve been noodling the idea of Forums for Rands in Repose for over a year. Some of the most interesting articles on the site have little to with my reposings and everything to do with people taking the time to comment on my original thought. Forums seem like a natural way to encourage the growing Rands in Repose community to interact, but the problem has always been — the tools suck.

Over the past few years, I’ve installed and toyed with both PunBB and vBulletin on my server. Each time I thought, “You know, all I need to do is announce this to the public and we can start this experiment.” Folks will show up and, if past comments are any indication, they’ll have something to say. Problem is, forum or discussion board software just looks boxy and rigid and I’m messy. I live my life in my inbox and my inbox is an insatiable growing beast. Sure, I like to give myself the impression that I’ve tamed the beast with mail rules and filters, but the fact is, I’ve got 5000+ unread message in my inbox that I’m never going to read.

Still, that is how I think about conversations. Not in structured discussion groups, but in a firehose of a queue that I can slice, dice, tag, filter, sort, and whatever other verb makes my info_surfing easier.

Enter Lussumo’s Vanilla forum software. I found this software July of last year, and, like any great tool, I instantly thought, “Yeah, I can build something with this”. It’s not the prettiest software out there; it doesn’t have the most features, but what it does have is instant software sex appeal. When you first look at it, you don’t think, “Golly, which discussion group should I search?”, you see everything that folks are talking about right this second. What Lussumo gets that others do not is that I’m not interested in building a discussion forum, I’m building a community. The success of piece of social software is an easy measure — how long does it take one person to find people they should talk with?

Jump Starting the Forums

The forums are an experiment and by experiment I do mean, “I’m going to keep tweaking it, throwing stuff at it, and then we’ll either call the experiment a success or a failure”.

- You can browse the public forums without an account, but to post, as well as access all the forums… including access to the slush pile of articles that didn’t quite make it to the front page… you’ve got to create an account. I realize this hoop will decrease the number of folks who sign up and I’m “OK” with that fact.
- I’m new to the whole forum thing, so I’d definitely appreciate constructive criticism, feature requests, and whatever other members think would improve the experience.

Let’s begin…

Developer 2.0

Right this second, there are five books sitting on my desk. I’m not talking about the invisible books stacked up next to my monitor, I’m talking about the books I want you to see the second you walk in my office. They change over time, but right now they are:

• The Phaidon Atlas of Contemporary World Architecture
• Post Secret
• Stop Stealing Sheep & Find Out How Type Works
• Antoni Gaudi
• Universal Principles of Design

My degree is in Computer and Information Science. I spent four years grinding on the basics of developing software, yet, strangely, there are no programming books on my desk I do have these books, stuffed on nearby bookshelves, but these are not the books I pick up when I have five random minutes. I pick up the architecture book and read the blurb about the Canary Wharf Underground Station in London. It describes a subway station design with a high degree of visual transparency between floors which means there is very little need for supplementary signage.

I spend the rest of the day staring at signs and absorbing the irony that while signs are trying to make my life easier; they exist because of basic deficiencies in design.

Yes, I’m a wannabe designer. It started four years ago when I opened my first iPod and read the following:

“Designed by Apple in California.”

This is not marketing; this is advice.

Designers Need Developers to Make Their Products

I listed the top three themes from SXSW a couple months back, but the entry did not capture the holy shit I took from Austin. SXSW is a gathering of music, movie, and interactive enthusiasts. On the plane to Texas, the game of figuring out which person belonged to the different aspects of the conference began… Yeah, the music folks look like music folks… edgy… arty. The movie folks dripped with glamour and intense LA energy. What about the interactive folks?

Wait, what does interactive actually mean? I still don’t know.

My impression is the interactive portion of SXSW is a mutated version of what used to be the multimedia portion of the conference. You remember this fad, right? When everyone got crazy about pouring all sorts of content onto CDs and Macromedia Director was king? Developers were scratching their collective heads during these times because no one was inviting them to multimedia conferences. Their thought, “They’re building software, right?”

Wrong. The multimedia types were thinking, “It’s bigger than software, MAN… We’re building complex interactive multimedia experiences. It’s not ones and zeros, MAN… it’s SOOOOOOUUUUUUL.”

Right. So, it’s software. Simply because creatives could hide from software engineers behind their authoring tools didn’t mean they weren’t developing software. It just meant they had a comfortable space to live in where they could design, not program.

Over the past few years, someone started inviting developers to SXSW. Designers discovered that whiz bang Web 2.0 technology heavily intersected with their domain, but they also found the tools were primal. There is no Director for developing web applications because everyone is still trying to figure this shit out.

Designers have two choices. Either dip their feet into the programming pool and learn this frontier technology, or figure out how to speak developer. This leads to part of the beauty of this year’s SXSW. Tables full of passionate designers and developers. Both parties buying each other drinks and silently staring across the table thinking, “Shit, I really need this guy, but I totally don’t speak his language.”

Which leads us to…

Developers Need Designers to Make Their Products Work

The third hire at the start-up was an interaction designer, Barney. When I arrived several months later, I thought, “Swell, someone to make pretty pictures of my product. That’ll sure make presentations easier because I suck at drawing.”

In our first design meeting, I was shocked when Barney was running the meeting and there wasn’t a pretty picture to be seen. He had these low-fidelity wireframe designs of the product that weren’t at all fun to to look at. After twenty minutes of staring at them, I realized they described how our product fit together.

Me: “Wait wait, wait, Barney, page two… Are you sure that’s how it’s supposed to work? That makes no sense to me.”

Barney: “Rands, you aren’t the customer. I’ll explain why.”

In the months before I arrived at the start-up, Barney had gotten into the the head of our target customers. He’d spent weeks onsite withpotential clients and he grilled them and he captured every nugget of truth about what they cared about. Three years later, Barney was long gone, and we were still flipping through his specifications… searching for inspiration.

Barney’s lesson was simple. Design for the customer. It doesn’t matter if it’s HTML, C, Python, or Ruby on Rails. Your job as a developer of software is to build software which works for human beings and there are conferences full of bright people who are well versed in cognitive psychology, usability, visual design principles, and art. The problem is you aren’t going to these conferences and soaking in their experience. It turns out that is a career limiting move for both of us.

You Can’t Offshore Art

There is a person sitting somewhere on the planet Earth who is capable of doing your job for a lot less money. I know what I said, jobs which lend themselves to a well defined process will be the first to go, but that will change. Each year that passes, more technology and infrastructure spreads across the globe and anyone with a computer and connection to the Internet has a chance to build the skills to develop software.

If someone figures out a useful way to integrate remote workers as a team, the Silicon Valley software developer has a problem. How do you compete with an equally skilled developer who is willing to do your job for half the cost? Do you know what the biggest expense is for a software development company? That’s right, it’s your salary. If I could figure out how to effectively engage a remote team, I could build a virtual team of developers that could be twice the size of my local team, but I won’t do that because I’m not hiring developers for my next start-up. I’m hiring designers.

When I’m building up the next development team, each of my hires will need to demonstrate they can talk maniacally about a slice of design. Maybe they’ll care deeply about color theory? Architecture? Interaction design? I don’t care, but they must be passionate about something other than writing fast, bug-free code because software is art. We don’t need another Microsoft Word, we need the next word processor and that’s going to come from a small group of people with a delicious interdisciplinary mix of design and development skills.

So, take a small leap. If you haven’t already, go buy this book. It’s full of bite-sized design ideas. Soak in it and prepare for your next job.

The Wet

All you needed to do this winter to figure out that we screwed up the planet is stare out the living room window. This here is day number four of snow that stuck up here at fourteen hundred feet in the Santa Cruz Mountains of California.

We get a smattering snow ever so often, but it was close to thirty years ago that we had anything which resembled close to a week of snow worthy weather.

When you follow the snow with close to forty days of rain, you can imagine the feeling when the back yard starts to look like this.

Happy Spring.

1.0

Max was a mess. We were on our third mojito at The Basin in Saratoga when it just came pouring out of him. The last 72 hours involved:

• Two days in Los Angeles babysitting a customer’s data center
• Four hours of sleep
• Two huge arguments with his wife on the cell phone
• A marathon conference call with his boss, which resulted in a new trip to Chicago in two days

The mojitos might’ve been talking, but it sounded like Max was sure that his wife was going to leave him; his company was about to crumble; and he was 12 hours and one plane flight from a nervous breakdown.

He said, “Shipping a 1.0 product isn’t going to kill you, but it will try”.

Understanding 1.0

In your career as a software developer, you’re going to be screwed at some point. I’ve got you covered there. Start here, keep thinking, don’t yell, treat those you work with decently, and you’ll be fine. It’s valuable experience, but it’s nothing compared to 1.0.

1.0 is developing the first version of a new product. It’s what all those start-ups are busily doing right now. They’re working on some 1.0 idea that’s good enough that a handful of bright people will forgo their lives in support of the chance of being right… SEE, we had a great idea… We’re bazillionaires and we were right.

Most of those start-ups fail.

Before Fucked Company, failing was a quiet, somber thing. The dot-com explosion made colossal flame-outs front page news and everyone discovered what most of us already knew.

Really. Most start-ups fail.

Why?

To understand the difficulty of 1.0, I need to give you a model for understanding how a 1.0 software product actually shows up. I’ve designed just such a model by heavily borrowing for a theory known as Maslow’s Hierarchy of Needs, which is worth talking about all by its lonesome.

Maslow’s theory contends that as humans meet their basic needs, they seek to satisfy successively higher needs that occupy a set hierarchy that looks like this:

At the bottom of the pyramid is the biggest area of need: physiological needs. These are the basics: food, drink, air, sleep, etc. The idea is that you won’t be able to focus on anything else in the hierarchy if these needs aren’t met. Think of it like this: who cares about falling in love if you can’t breathe?

Moving up the hierarchy, you have safety needs, love/belonging, esteem, and, finally, the oddly named self-actualization tip of the pyramid, which is our instinctual need to make the most of our unique abilities. Translation: writers write, singers sing.

There’s a fine entry in Wikipedia regarding Maslow’s Hierarchy if I’ve piqued your interest. Personally, as a manager of humans, I stare at the hierarchy when dealing with folks on the edge. The Hierarchy gives me insight into where exactly a person is stressing out. Are they in need of career advice? (Easy) Or do they need marriage advice? (Harder)

Rands 1.0 Hierarchy

In thinking about the difficulties of 1.0, I realized that Maslow’s model fundamentally applied to shipping the first version of a product. There’s a hierarchy that defines what you need to build in order to ship 1.0 and it sort’f looks like this.

Sidebar regarding Charts’n’Graphs: Phillippe Kahn, the founder of Borland, told a great story about statistics that I think equally applies to Charts’n’Graphs. The story is, “Did you know it’s a statistical fact that people with larger feet tend to be better spellers? [insert awe] It’s because people with bigger feet are older.”

Charts’n’Graphs paint the world in a clean, linear fashion that serves one purpose: support the message of the author. Do not trust Charts’n’Graphs, but don’t let that lack of trust blind you to the intent of the story.

Pitch

At the top of the hierarchy, there’s Your Great Idea. I’m calling it pitch because I’ve got this alliteration thing going on. You can’t get anywhere in building a product or a company without a phenomenal pitch. It doesn’t matter if you’re Mr. Charisma; you’ve got to have the idea because it defines the structure and constraints of everything below it. If you don’t have the idea, you don’t know who to hire, which is the second layer — people.

Before we talk about this second layer, let me first congratulate you. I’m tripping over myself happy that you’ve discovered the Next Big Thing, but there are some basic facts to pay attention to. The first is:

Fact #1: You’re in a hurry

You’re a fool if you think you have exclusive rights to your pitch. There are too many bright people staring at exactly the same infinite pile of evolving information to assume your innovation is original. The only thing that gives you this right is delivering 1.0 and first, you’re going to need some people.

People

With your pitch in hand, you’re going to find the people to build your idea. These are your founders. These are the folks who will not only build your 1.0, but, more importantly, your engineering culture. Their arrival presents a challenge and a twist to the pyramid.

Your first few hires walk into a blank slate. Sure, they’ve got you, the keeper of the Great Idea, with your pitch and endless enthusiasm, but they don’t know where to find the bathroom. More importantly, they’ve got to digest the pitch and start to build your 1.0.

The moment one of your founding engineers starts writing code he/she is making a decision about the eventual product. It the first of innumerable decisions which will be made and as the Keeper of the pitch, you’re probably going to try to stay involved, but simply can’t be there for every decision. What you should be focusing on is the pitch. Your job is to listen to people and continually refine the idea so much that it can guide when you’re not there to clarify. This leads us to our twist. The Rands 1.0 Hierarchy is much scarier than Maslow’s because it looks like this:

There’s a good reason why folks don’t build their pyramids like this — they fall over. The only way to keep them from falling over is to constantly push one side or the other. This is your start-up. This impractical concept with your pitch sitting at the bottom… defining everything above it. What will kill you about 1.0 will be how much time you’re going to trying to keep this pyramid balanced, which brings us back to the topic at hand, people.

Fact #1: No one is indispensable

Now, I’m a people person. This entire weblog is devoted to figuring out how to make sure folks get along and get stuff done, but we’re not talking about an established company here, we’re talking about 1.0 and the rules are different because you are an unknown quantity and everyone is expecting you to fail.

Ever built a fire? What do you need? A match, some paper, and some kindling wood that catches fire easily. Your first three hires are your kindling. Their job is not to define the product roadmap, their job is to get things moving, and if things aren’t moving, you need to get some more wood.

At my start-up, I was brought in as the first engineering manager. The Founders had brought on two Free Electrons with totally different temperaments. One was burning the midnight oil on getting a working prototype done. He was fully aware we’d throw the whole thing away, but he knew that the ability to see the idea in code would change everyone’s opinion of what we were doing. It would make the pitch real.

The other Electron also loved the pitch, but he was working on infrastructure for future products. HE WAS WHAT? Yes, we had no product and one of our key hires was already investing in the future. When is investing in the future a bad idea? How about when the now is not defined? The Free Electron was working under the assumption that 1.0 would be successful and while I appreciated his enthusiasm, let’s remember Fact #0: Start-ups almost always fail.

I spent some time with the Free Electron and, as it often goes with very bright people on a mission, it was clear he wasn’t going to be swayed, so I let him go. That day. One quick meeting with our VP and it was done.

If you’ve read my article about Free Electrons, you’ll know that you don’t run into these types of stunning engineers very often. Firing a Free Electron is pretty stupid for most companies because they have so much potential, but here’s the deal: you aren’t a company until 1.0 is done. A great way to topple your fledging pyramid is to hire folks who are not getting the product done with a sense of urgency. Get 1.0 done and then worry what’s next.

Process

There is no word that irks engineers more than process. Try it right now. Get everyone in your office and say something like, “I’ve defined a new process to assist our bug triage”. Watch their faces sag. They hear “busy work”. They think “management is trying to justify itself”.

This is not the word that defines the third level of the Hierarchy.

Fact #2: Process defines communication

Process is the means by which your team communicates. Whether this is via a wiki, email, or the hallway, any team larger than one needs to define a means to share information. This is not an argument for specifications, documentation, or a whiteboard filled with do’s and don’ts. You just need to agree how you’re going to share information.

When your second engineer decides, “Yes, I’m going to capture my design decisions in a wiki”. That’s process. When your third engineer starts tracking bugs on that huge whiteboard in the meeting room, that’s process. It doesn’t have to be good, it doesn’t even have to be universally agreed upon on, it just has to be stuck in a place where every can see it.

SourceSafe was the repository of choice when I landed at my first start-up. Stop laughing. It did a fine job of with a team of six engineers who had zero time to worry about source control. Sure, it was slow as a hell and lost a days work here and there because of various hiccups, but we were working on 1.0 and who had time to think about something more reliable?

Roland did.

Roland was a junior engineer and he was a Perforce fan. Roland did what any good employee of a start-up would do. Over the course of a weekend, he set up a Perforce server, rewrote all of our build tools, and scheduled a 10am meeting on the following Monday, promising Krispy Kreme donuts. His message: “This is the way it is. Everything works better. Thank you and have a donut.”

In a weekend, Roland fixed a major flaw in our process (crappy tools) and also demonstrated another fact of the hierarchy.

Fact #3: Each layer shapes and moves those near it

A sure sign of a healthy pyramid is that one layer invades another. Think of each change to people, process, and pitch as a shove in one direction. This movement requires compensation in the other layers otherwise the whole thing falls over. Roland’s decision to change the engineering process pissed off some folks. We lost some time to some source management edge cases that Roland hadn’t thought of, but, within a week, we’d adjusted. Even the most vocal opponent of the change ended up in Roland’s office arguing about how we could make it better.

If, in your organization, your pyramid is not constantly adjusting to keep itself upright. Something’s wrong. If the new folks aren’t testing the pitch, they either don’t buy it or they don’t get it. If your engineers aren’t arguing about the way they develop software ALL THE TIME, they’re becoming stagnant and that trickles down to your pitch and trickles up to your product.

A great stagnation warning sign during 1.0 is when someone decides to create an organization chart defining “This is who does what”. Now, investors and outside parties need this org chart to get a sense of whether you’re real or not, but your 1.0 team does not. The whiteboard in the corner of the room, which lists who is doing what, is your org chart. The definition and hierarchy an org chart portrays is the first step in creating a culture of secrecy in your org. That might work for Apple, but you’re not Apple, yet. You’re hope and hard work.

Product

At some point, you’re going to need to fake being done. You’re going to need to release something which barely looks like your pitch because you don’t have product until a neutral party stares at something.

Fact #4: You don’t have a company until you have a product

Product is not pitch. Pitch is the three sentence idea which gave you the credibility to hire the people. The people argued about the pitch, they created process to refine and develop the pitch, and that changed it. The pyramid wobbled hither and fro during all of this… maybe it fell completely over and you scrambled to stack those layers up again. Good job, there. You still don’t have product.

The neutral parties, your customers, need to see what you’ve been building because all your people are completely insane. All that healthy shifting of the pyramid has been taxing them. Each shove forced them to adjust their perspective of the pitch, their relation to it, and adapting to change is fucking exhausting. Folks who say, “I like change” are not currently working at a start-up. Folks at a start-up don’t say much because they’re busy adapting to the latest pyramid shift.

This state of constant change is the leading cause of start-up burnout and it’s also the reason you’ve got to get that product out. The perspective of the neutral party is essential validation because you’re nuts. Your pitch has been dissected and redefined so many times that it may no longer be something that is useful. A neutral party doesn’t care about the pitch, your people, or any of the pyramid shoving you’ve been up to; they just care whether the product is useful.

Using the Pyramid

At no point will you ever draw this hierarchy on a whiteboard during an organizational crisis and say, “FOLKS, PAY ATTENTION TO THE PYRAMID — SO SAYS THE RANDS”. The idea is to give you a tool that reminds you, “Hey, it’s all connected!” The pitch guides the people. The people refine the pitch. People and pitch create process and product, and, yeah, it’s all a big mess and that’s why start-ups fail.

The pyramid gives you a hazy map to think about the problems your company might face. People will yell in the hallway and it might sound like they’re arguing about product, but keep listening, maybe it’s process. Even worse (better?), maybe it’s pitch. Your one job as Keeper of the Pitch is to figuring out which layer of the pyramid is being tested and then figure out which way to shove the pyramid. This leads us to our last fact:

Fact #5: The lower the failure, the higher the cost

A year into my start-up, the Founders were at a crossroads. We were doing an enterprise web application that was built for onsite deployment. Problem was, everyone was going loopy about hosted services. The pitch there was: “Look how much time and energy I’ll save you by hosting this application in my data center, not yours”. This idea flew in the face of years of Oracle, PeopleSoft, and IBM domination of that huge pile of business software and hardware sitting in your data center, but it was the Internet… and the Internet was going to save the world.

The Founders changed their pitch. “We’ll just create copies of the software in our data center! We’ll save money keeping our bits close to home!” No huge difference there? Wrong. This adjustment to our pitch changed the engineering with the addition of a data center component and, more importantly, it fundamentally changed the architecture of the product. Rather than have hundreds of customized versions of our software sitting in various data centers, we had to have one copy of our software which was configurable to each of our customers needs and that wasn’t the product we designed.

It wasn’t an instant disaster. We had piles of money to throw at this transformation, but the transition cost became so great that we stopped working on anything except getting the hosted application working and, right about then, the bubble burst.

Let’s call failure a really bad decision. It’s when you choose to change something and that change percolates up through the pyramid. If you make a bad decision regarding version control, well, you can probably adjust to that. You can fire a Free Electron and probably find another bright person who can channel the pitch better, but you’re probably going to rattle more than you think. A failure of pitch is a structural failure that affects your entire company. Everything in your company depends on the vision that you’ve presented and screwing that up can be fatal.

Building Culture

If you’ve actually got a pitch ready to go, again, that’s terrific. This totally conceptual model I’ve thrown together doesn’t cover some major topics that you need to understand. How are you going to fund this thing? Where do you find VCs? Where do you find great people? Your life will become an endless list of questions and decisions and you’ll probably forget everything I just wrote in your frenetic sprint to keep your pitch alive, so I’ll simplify. The hierarchy I describe is not a model for how to build a great product; it’s a picture that describes the culture of your company. That’s what you’re really building in 1.0. A lasting, interesting culture which, if you’re lucky, continues to produces great products.

Think of your five favorite companies and think about what made them successful. Yes, they probably had a great 1.0. Think Apple ][. Think of the first time you saw Netscape. Those products are the end result of people killing themselves to get the damned thing out the door, but they weren’t just creating that product. Their work defined the culture of the company and that is what modeled their future success.