Appreciating typography is a study in paradox. The primary goal of well-designed typography is to help you read the words, not appreciate how the words are composed of letters and how each of those individual letters has been designed to convey a small bit of meaning. If you see the typography rather than read the words, the typography has failed in its job, right? You should be reading, not staring at the shape of that uppercase A.

The goal with typography is functional, right? To convey the meaning, not the feeling?

Wrong.

Feeling is always conveyed. The question is, depending on the project, “How much feeling is required?”

Fixed Width

I’ve created a full-time job for myself talking to Claude Code. This is Claude running from the command line of macOS, which gives me unhindered access to my data. I’m using Ghostty. I’m staring at a fixed-width typeface all day. Apple provides a functional and gorgeous fixed-width variant of their San Francisco typeface called SF Mono, which I’ve been using for months, but, well, I have a short attention span — typographically speaking.

In the past month, I’ve evaluated many additional fixed-width typefaces favored by the nerdcore. Here are the six that have made my cut:¹

The question is: how do they make you feel? For a typeface designed for coding, you first want fixed-width. Every letter and symbol is the same width, giving you a predictable and readable grid. But how wide? And how tall? Also, how much information do you want to be able to see on a screen?

Your brain builds a very personal and emotional impression of the collection of letters that make words that convey meaning. In the case of terminal or coding typefaces, the design goal is certainly to provide structural function and not feeling, but here’s the deal:

They do.

Isn’t this about the Blade Runner Title Sequence?

Flight to New York. My boarding procedure for moderate to long flights is: sit down, find a movie I’ve seen a dozen times, and hit play. No sound. This is visual background noise while I sort wifi, prepare for a meal, and find a project. On this flight, I picked Blade Runner. Fun fact: I can recite 50% of the dialogue from this movie from memory.

As I’ve been researching typography for Ghostty, novel typography tends to jump out at me. Like when you buy a car, and all you see is your new car on the road. Except it’s typography.

Here are clips from the title sequence for Blade Runner:

There’s a lot to dissect in this sequence, but let’s start with the punchline. This is a single typeface. It’s Goudy Oldstyle — that’s it. However, this is how they used typography:

• ALL CAPS for names, proper names, the title², and a slightly larger version for the introduction of Los Angeles, November, 2019³
• A smaller ALL CAPS for intros and other small important words
• For the exposition crawl, they use standard capitalization except for two variants: small caps for proper names (like The Tyrell Corporation) or (spoiler alert) a red version of the text for the word Replicant — which is italicized every time it appears, but only the debut gets the red — and (spoiler alert) it’s the same red as the title of the movie⁴

Keep looking. The crawl is set like a book, not a movie — first-line indents, generous word spacing — and Frederic Goudy would approve: they letterspace the caps, never the lowercase, obeying his famous dictum that “anyone who would letterspace lowercase would steal sheep.”⁵ Also, what’s up with that chonky em dash? It’s probably been years since you’ve seen this, so here it is again:

Unlike our functional fixed-width typefaces, the role of typography in this title sequence is partly functional — to set the story — but the primary purpose is establishing mood. Director Ridley Scott expertly drops us into the middle of a dystopian future where we’ve enslaved the robots and, duh, they are rebelling.

How Much Feeling is Required?

Chances are, you never think about typography. You happily scribe your Messages (SF Pro), Mails (Helvetica), and Slacks (Lato), thinking nothing of serifs, ligatures, or kerning. You are content trusting that a someone else has chosen a proper typeface for your current task. Maybe you bold, you underline, and you italicize to slightly adjust meaning. No issue. Respect.

However, we now live in a world where everyone is capable of building whatever they want thanks to the robots. They’re doing it — right now. They find immense joy in typing in a couple of sentences and watching the robots merrily build whatever they ask. See? I don’t need to be an engineer to build an app. And they are correct. Sorta.

With optimism in my heart and a firm belief that the robots can legitimately help many humans, I can confirm that the majority of consumer-facing things being built by humans who’ve never built a thing… are garbage. Building a tool for yourself? A quick script to read your feeds and generate a pleasant-to-read output? A+. Robots crush that… for you. Building a feed reader anyone on the planet can easily use to read any number of feeds? No. No, you aren’t; you can say you are, but until you’ve built a thing for everyone, you will not appreciate that the last 10% of the work:

1. Takes most of the time.
2. Contains an endless list of small decisions that feel unimportant, but collectively make the difference between acceptable and fucking amazing.

Don’t believe me? Here’s the first version of the title sequence for Blade Runner’s work print, the close-to-complete cut before the theatrical release:

That title typeface? Impact. A fine typeface, but a clumsy path-of-least-resistance slap-to-the-face choice to set the tone of a future science fiction masterpiece. Garbage⁶.

I’ve never filmed a movie, but I have built quite a few products that you are using right now. In all the design debates, we never explicitly debate feeling: we obsess over the details. That obsession is what you feel when you use our products. It’s the collective voice of every single human who contributed small and large decisions to the product.

A good product sounds like the humans who created it, and that’s what you will feel.

1. As I type this: IBM Plex Mono. By the time you read this: anyone’s guess. See: short attention span. ↩︎ 
2. Type nerds, yes, I know the title of the movie is hand drawn, but it’s certainly inspired by Goudy Oldstyle ↩︎ 
3. Hey LA, I might rip on you because you steal our water, but you’re doing better than Ridley Scott predicted. Good job. ↩︎ 
4. It’s been there all along, folks, why did we argue for all those years? ↩︎ 
5. Type nerds: Goudy’s original grievance was reportedly about blackletter, not lowercase. The lowercase version is the misquote that stuck — Erik Spiekermann liked it enough to name a book after it. The rule holds either way. ↩︎ 
6. Yes, it doesn’t help that there is no Vangelis soundtrack, yet. ↩︎ 

The final measure of any financial negotiation is the feeling of whether or not you got a “deal”.

That prior sentence… makes no sense.

I wrote “measure,” and then six words later I wrote “feeling”. A feeling is never a measure, but yet, when you hand over your hard-earned money to buy a thing, you’ll feel better because you believe the value received is higher than the dollars paid.

Too abstract. Here’s a good example:

I have felt since it was announced that the Apple iPhone Upgrade Program has not just been a deal, but a steal. The specifics:

• You apply for a loan for a full-price iPhone at 0%.
• If approved, your payments are split over 24 months.
• Pay for 24 months, and the phone is yours.

That was just the deal; the steal was that it was low effort every single year to get a new phone. I’d re-up for a new phone, and Apple would forgive the remaining payments of the loan because I’d signed up for another 24 months. Oh, and bonus, AppleCare was included, which was a total steal because I hate iPhone cases (iPhones are designed to be felt) and, uh, also I have been known to drop my phone.

Felt fair. The Apple bet was that users would embrace the original plan, were going to re-up regularly, and Apple would refurb the phone on a strong used market. That bet ended on a Tuesday. Apple retired the Upgrade Program and replaced it with Apple Upgrade: a Klarna-financed lease covering iPhones, Watches, iPads, and Macs. The loan became a lease. And it feels different.

Follow the AppleCare Money

At first glance, the new plan looks cheaper. The original plan: one year of iPhone 17 Pro (256GB, $1,099 sticker) was ~$57/month. 12 payments, trade-in, restart: ~$684 for the year. The new one, same phone: $45.99/month on the 12-month lease: $552 for the year.

But wait! The first and most important change to the new plan is that AppleCare is no longer included. Adding it back to this phone at $13.99/month: $720 for the year.

But hold it! You can pay for AppleCare annually at $139.99, which brings the year to $692 — eight dollars from the original plan.

But wait once more! You have AppleCare One? Well, good news, your new iPhone can ride along in a $5.99/month slot, bringing us to $624 for the year. In fact, and illuminatingly so, the only way to get the good price on iPhone-plus-AppleCare is to get three pieces of hardware on the AppleCare One plan, which means having three pieces of hardware.

This might sound reasonable until you think about the number of times I’ve never had the opportunity to drop my Mac Studio. For all Mac hardware in general, there was that one time Rands Jr. somehow cracked her MacBook screen. That one time — in a couple of decades.

AppleCare is insurance. Like all insurance, you pay for protection from expensive, but hopefully unlikely disasters. In the event of the unlikely, you don’t pay. My issue with this approach is it appears Apple is removing AppleCare from the upgrade plan and herding folks towards AppleCare One because margins on insurance are sweet — like 2x the margins on hardware. I already pay Apple insurance. It’s not called insurance; it’s called “incredibly high quality hardware.” I gleefully pay Apple a premium not just because of its cutting-edge design, but also exemplary quality. With Dell, I pay for the insurance because the motherboard on my fancy Alienware gaming PC has already failed once.

It Still Feels Like a Deal, Not a Steal

When I buy a ticket at United, just before I click purchase, there is a must-acknowledge box I am required to read. It is a light-fear-inducing reminder that “Stuff changes when you are flying. You never know, but… maybe plop down a couple of hundred dollars because, well, you never know and we know better so maybe yeah, pay us money, and we’ll make it ok.”

Never in the history of ever have I done this. Yes, in the middle of winter when travel plans are truly up in the air, I think about it, but mostly… gross. This is a business trying to eke out high-margin dollars just before the sale when you are most worried about the value of your purchase.

There is genuine value in AppleCare, and I’ve considered AppleCare One because the Rands house has a lot of hardware, but the more I stare at the new plan, the more I feel a little gross.

I’ll stick with the plan for the phone along with additional AppleCare (not AppleCare One) because, remember, it’s whether or not I feel I got a deal. The primary intangible is that Apple is quite good at operations. The process of re-upping for the new phone has historically been trivial.

• After the new phone has been announced, click a couple of things in the Store app, and you’re done.
• New phone arrives promptly along with a pre-labeled return box for your old phone.
• Drop that box off at FedEx. And done.

New phone sitting at the door. Almost like magic. Almost.

The Apple Upgrade Situation

the loan became a lease

Apple retired the decade-old iPhone Upgrade Program for a Klarna-financed lease. The monthly price dropped; the AppleCare money moved. Follow it.

Lots to digest here. I’m here for you. Read the Grumbles-infused analysis. A well-sourced scoreboard of who won and who didn’t.

Why do I write? I write because I like the mental state created by writing. It calms and quiets me, but that is not why I write.

Why do I write? I write because I am curious and like to understand the world. Writing forces me to understand a thing, a person, a situation. I don’t think many humans do this, but I am addicted to it. But that is not why I write.

Why do I write? I write because I like helping. People are often the worst, but I have a desire to help. This internal contradiction is confusing. Humans who approach me looking for Rands, but find Lopp, are disappointed and confused because Rands helped them and Lopp apparently couldn’t care less? Introvert. But helping is not why I write.

Why do I write? I deeply believe it is important for humans to build stuff. I think this is a primary reason we are on the planet, and I think that the ways a human can build are as varied as the humans who do the building.

Failure to build is abhorrent to me. Much of the anger on the planet right now is from humans who aren’t building, believing they are owed a free lunch because they showed up, or they know better, or some other poorly informed worldview they acquired without effort, without curiosity… just because they exist in their particular circumstances.

Writing is how I build. That’s why I write.

You will never do 150% of a thing if you do not have a version of these motivations. 15% effort means you have not found your reasons yet.

One hundred episodes. For this occasion, years in the coming, Lyle and I talk about the thing itself — the nuts and bolts of the podcast, including how the robots now do an alarming amount of the work, what a hundred episodes taught us, and why we use the “The One About…” naming convention.

🎁: the show has a home at importantthing.show. Deep-link a favorite or just scroll through a hundred episodes of history.

Stuff that came up:

• Riverside, where we record the show
• Rands Leadership Slack, now staffed by a helpful jobs robot named Floyd
• Planetfall, the Infocom classic Floyd is named after
• Friends, the homage hiding in plain sight in every episode title
• Marco Arment, listening since at least my fiftieth birthday

Related Important Things episodes:

• EP 56: The One About the Month of Podcasting
• EP 51: The One About Names… Again
• EP 98: The One About The Joy of Bots
• EP 18: The One About Sugar — Lyle’s favorite, as heard on-air
• EP 78: The One About Sandwiches — the other favorite
• EP 96: The One About ARC Raiders — the first episode the robots dressed up

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

In our 99th episode, Rands is back on the Pro Leisure Circuit — infinite time, a suspicious amount of Arc Raiders, and no wind in the sails — and we wrestle with what actually motivates a person when the engine of work goes quiet.

The usual suspects:

• Arc Raiders, absorbing ten-hour days like it’s a job
• Rands Leadership Slack — 35,000 leaders, 7,000 a week
• Daring Fireball, John Gruber’s one-person media entity
• Ray Kroc, who started McDonald’s in his fifties
• CalArts, where Lyle’s daughter learned she didn’t want to animate for a living
• UC Santa Cruz, Lyle’s decade in the state of California

Related Important Things episodes:

• EP 25: The One About the Pro Leisure Circuit
• EP 96: The One About ARC Raiders

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

Review season. You start your career thinking the review is the most important milestone of the year, but as an individual, you only see part of the picture.

Everyone cares about the compensation (base salary, bonus, and stock). That’s the data they care about, but where did this pile of compensation come from? Who decided how big it is? And how is it allocated? It is a long, complicated, and large process that began over a year ago.

And as a Senior Leader, it’s your job to figure it out.

The Most Important Milestone

I’m going to work backward because we’re all — correctly — focused on compensation. Before I do, one thing to hold onto, because it’s the thing that trips everyone up: in any given Summer, two budgets are moving at once. One is being spent — the money for this year’s raises, which was locked in a year ago. The other is being built — next year’s budget, which is just now getting decided in rooms most people never see. Keep those two apart in your head, and the rest of this article is more digestible.

Disclaimer: This article makes a lot of assumptions, which I’ll explain as I go. The first is that you work in a business that is doing well enough to afford a merit budget for the team. No merit budget? Probably no promotions and likely no raises. Reading this article is still worth your while.

Fall. Reviews. Critical milestone. You receive a letter that says some words and then has some numbers. Hopefully, your boss explains these words and these numbers and gives you context on what they mean relative to your performance. I have found that the number of words I’ve received as a Senior Leader has gone down as a function of seniority. The number usually goes up. Usually. Why the Fall? It’s the last moment the company can pay out against a budget it defined a year ago, before the next fiscal year begins.

Earlier that Summer. Another critical milestone/meeting. Talent Planning. Before the review is written, the Senior Leaders for a team gather together and debate some version of ratings. There are many variants of these ratings for each company, but the punch line is that for each level (basically senior, mid, and junior), an employee is put in one of four performance buckets:

• Exceptional
• Strong
• Fine
• Needs Work

Worth repeating now, because it matters later: the money you’re allocating in this room was decided roughly a year ago. You are dividing up a pile whose size is already fixed.

If you’ve had the opportunity to be in one of these meetings in your career, you realize the intense hand-waving I’m doing with these four bullets. Get used to it. I’ve run eight versions of this process over the last 30 years, and I’m providing a high-level description without many details. However, the principles behind this process are the same.

Sidebar: If you haven’t had one of these meetings, I wonder why. How are you calibrating your ratings with your peers? How are you making sure your ratings are fair? Good questions that deserve answers.

Back to the meeting. The tricky part of this Talent Planning process is the constraints:

• For a given team, there is a limit on how many individuals can go in each bucket, and
• For a given rating bucket, there is a limit (usually a range) on how much comp can be allocated to an individual.

These counts and ranges vary by level. More junior folks can receive higher ratings. The higher the level, the higher the compensation range. If it’s not obvious yet, these restrictions exist for two reasons:

• By restricting how many humans can go in each bucket, the company enforces a curve for ratings.¹
• When you add compensation ranges to all of it, you have all the pieces in place for a budget. X humans at Y compensation equals the total budget for raises.

These restrictions exist because every manager believes their team is doing better than other teams. This is normal human behavior; they better understand the data in front of them than the abstract data sitting in someone else’s head.

Psychologists call this the Lake Wobegon effect, named for the fictional town where all the children are above average. Your team’s work is vivid because you’re standing next to it; everyone else’s is a bullet on a slide. It’s not a lie — it’s a bias, and it’s why this meeting requires you to prove it.

However, without a mechanism that requires managers to defend their ratings, you get unbridled compensation and title bloat. That’s a future article.

Also, promotions are usually a part of this whole process. Some companies keep the promotion budget separate, but for the sake of simplicity, I’m tossing promotions into this Talent Planning process.

The Talent Planning process is essential. If you’re throwing promotions into the mix, you’re defining critical growth narratives for your most productive employees while also having honest debates about the unproductive ones. This article is not where I’m going to talk about how to do this well, when to debate, and when not to debate, or whether this process is fair or not. This is where I am looking at you, Mario. Yes, you. You and I have been Senior Directors on this team for three years, and every year, you think this is the meeting where we can argue for more dollars. I respect the moxie, but, Mario, this is not a budget meeting.

Your team, your organization, or your company carefully sets aside a chunk of money for compensation and promotions, and your job is to fit your plans for your team against this budget. Mario, yes, sometimes we pushed and discovered that the CFO or the VP had squirreled away dollars for the inevitable “We need more” conversations, but these were saved for one-off special circumstances. Our job is to hit our number.

Mario, do you want to affect this number? Good, wait just a few weeks.

Meanwhile Next Year is Already Happening

Everything up to this point — Reviews, Talent Planning, all of Mario’s arguing — has been about spending a budget that was set a year ago. Now turn around. Because in that very same July, while you’re sweating the ratings, a completely different set of meetings has already started: the ones that build next year’s budget. Same month. Different money. This is the cycle Mario never shows up for.

To vastly oversimplify even more, the process goes like this:

Strategy meetings — What are our big swings for the next year (or many years)? Product-wise. This often shows initially as themes or ideas from the CEO or VP of Product, and it’s designed to get a conversation started.

Product planning meetings — From that initial list of dreams, we (Product, Design, Engineering) start to build a defined set of concrete ideas that we could build. These are still scribbles, but on this long list of scribbles is the set of products and features the team is going to build in the next year.

Finance meetings — Once features start showing up, that’s when it’s time to get really uncomfortable. Important people are going to start asking hard questions about how much money it’s going to require to purchase that hardware or how many engineers will be required to staff that new feature or technology. If you’ve never done this before, my first bit of advice is: get comfortable with swags. While there are real dollars being decided here, you do not have the time to develop data-justified cost and headcount estimates. You are going to make well-informed guesses that have a significant impact on your team.

The cascade continues like this:

• Finance looks at the possible features and the costs and builds a forecast on how these new features could affect the business. They bolt that onto how the business is currently doing and start to make estimates on how much money can be spent on the various parts of the business.
• Quite often, the CEO creates working groups whose job it is to figure out different parts of the business. One of these working groups is the Compensation Committee, and its job is to figure out how much money the company can use in the next year for the merit budget based on finance guidance. They do a lot of research on hiring trends across the industry, promotion rates, and attrition rates, and then propose a number — “a 3.5% merit budget,” which means the budget is 3.5% of the total compensation of the current set of employees.

Every meeting I just described happens months before anyone writes a review. And the person whose budget depends on them wasn’t in the room.

Now Even Simpler

What’s my problem with Mario? He and I have been through this process three times now, and he still hasn’t figured out that the time to argue for more budget for his team has long passed. It’s not during Talent Planning; it’s during those Product Planning meetings he hasn’t shown up at for the last two years. His thought: I’m not a product guy — just tell me what you want me to build.

The wheels that are set in motion during Planning Meetings will define the budget that your team will be held to for the entire year. Chances are, they will never see a budget spreadsheet, but they will certainly feel the consequences of a budget where you did not successfully argue for headcount growth by drawing a clear line from strategy to product to features to the additional resources your team needs to get the job done in the coming year.

Arguing for a budget during a Talent Planning meeting demonstrates a profound lack of understanding of how business works. It’s all connected and, in business, it’s usually defined by money.

But that still isn’t my issue with Mario.

Has this article confused you? Is it completely clear how all compensation decisions are made? Probably not, but it gets worse. This is a model inspired by a consumer software company that ships annual releases — and you… work somewhere else. With an entirely different process.

And, as a Senior Leader, no one is going to take the time to explain all of this to you.

They are assuming you will take the time to figure out how the system works.

I’m looking at you, Mario.

1. Yes, a curve. Yes, your boss lied to you when you asked if there was a curve, and he talked for a while about fairness, but there’s a curve. Always. ↩︎ 

In our 98th episode, we list the things we’ve been building with our robots and figure out who we’re really yelling at when it all goes wrong.

Mentioned, referenced, or obsessed over:

• Planetfall, the Infocom game that gave Floyd his name
• Rands Leadership Slack
• Managing Humans
• Railway
• Supabase
• Bear
• Ghostty
• Cory Doctorow on centaurs and reverse-centaurs

Related Important Things episodes:

• EP 73: The One About Robots
• EP 83: The One About Your AI Tools

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

1. What’s it like to be you?
2. Where did you get your name? What’s your story?
3. What do you want to be when you grow up? What haven’t you done?
4. What do you want to change?
5. What are you most proud of?
6. What achievement are you most proud of?
7. Are you happy? What makes you happy?
8. Are you having fun? What do you do for play?
9. What is missing? What happened?
10. Why are you lucky?
11. What person/event changed you the most?
12. Who taught you the most?
13. Who do you trust and why?
14. What song is on repeat in your head?

I was sitting at dinner with dear friends, and we made a list of questions we love to ask.

I will now explain why at least 50% of your team finds your current All Hands to be a waste of their time. They believe:

1. This is information they can easily find elsewhere.
2. This is about you, not them.
3. This is boring.

Now, I will describe how to build an All Hands that will exceed their expectations. Let’s define the All Hands:

Everyone. Together.

There’s an important organizational inflection point when you need the All Hands. The basic definition is, “The whole team — together.” If you’re a leader of a team of seven, then you might think your team meeting is your All Hands and — strictly speaking — that’s correct, but that’s your team or staff meeting. Not an All Hands.

The whole team — together. This is a required meeting when the whole team is no longer able to be together organically. Is that 50? Maybe? Is that when they no longer fit in one room easily? Probably? The inflection point varies as a function of the company, but this is a required meeting because it mimics what you did instinctively when you were a smaller team, and that’s a good place to start.

When it’s you, Frank, Aki, Liz, Gigi, and Joshua sitting in the same room cranking on your start-up, what are the events that everyone needs to regularly understand?

1. What is the current state of the business?
2. When has something significant in the business changed?
3. What is important for us to do next?

In the same room, it is relatively easy to gather much of this information. You look around, see that Liz is on the phone closing her new head of engineering, and you think, “Go, Liz! I liked her candidate a lot.” Then you look over at Gigi, who has been quiet for two days and hasn’t smiled in four, and think, “She is the most focused designer in the world. I can’t wait to see what she’s done with our logo.” And so on.

The ebb and flow of information in a group of humans decreases as a function of population size. With growth, your ability to organically discern what is going on within the team decreases¹.

Pick a Format. Keep It.

It’s not just the ebb and flow of information, but the chance that Critical Piece of Information X reaches Correct Person Y. Each additional human creates another opportunity for important information to not reach its intended recipient.

As the senior leader, it’s trivial to forget this simple math because there’s a firehose pointed straight at your face. Your challenge is not the absence of information, it’s the abundance. Your challenge is picking out the signal from the noise while also not drowning.

The firehose is the primary reason for my first piece of structure guidance: pick a format for your All Hands and stick with it. Here’s the format I’ve been using for a couple of decades:

• Hello, let’s learn something.
• Here’s the current structure of the team and how it is different from the last time I showed this structure to you. If something huge changed or is about to change, there is room later to address this, or you can do it now.
• Here’s an opportunity to hear from my direct reports.
• Here’s a special guest.
• No Q&A. I’ll explain shortly.

I’ll explain the intent of each section in a moment, but the important thing to know right now is your structure will be different than mine, and that’s just fine. The point is not following my lead, but consistency. Anyone who receives an invite to this meeting understands broadly what to expect out of the meeting. Senior leaders who randomly do All Hands with fluid agendas at a time that suits them stress the team. When the unexpected and unexplainable meeting shows up, they instinctively think, “Uh oh. Someone’s in trouble.”

Tree Talk

We open with Hello. Nothing fancy. Over the years, a simple hello seemed empty. I wanted to do a little more than say hello while folks were still gathering and getting into the All Hands mindset. At the last gig, I followed Hello with a single slide called “Tree Talk,” where I spent a few minutes teaching the team something interesting about trees. One slide, a few facts. Totally irrelevant to the team, but absolutely essential to the culture.

Why? Because I believe curiosity is an intrinsic motivator. I don’t want the team sitting there as I drone on about things they already know; I want them to see what I care about. I care a lot about trees, but I care more about the team understanding the value of curiosity.

One Slide. What Changed.

This is often the most boring part of the presentation, except when it isn’t. This is a picture of your organization. “The org chart.” Your job is to describe what has changed since the last time you threw this up on the screen with a little color commentary.

• It will feel tactical and obvious, but as I said above, this is because it’s your organization, and it’s likely you were involved in whatever changes occurred. Zero changes? Really? OK, you still show the chart and briefly say, “Hey, nothing’s changed here. Next slide.”
• If massive changes have occurred since the last time you showed this, it’s worth cutting something from later in the agenda below in order for you and your team to explain what changed on the team and why.
• One slide. Never more. Yes, for a large organization, this means you’ll need to simplify or abstract out some organizations into simpler buckets. That’s fine — it just means you have subteams that need their own All Hands.

Not Your Show

The bulk of the presentation is not you, but some or all of your direct reports. What are they going to discuss? Up to them. The greatest hits:

• We built something!
• We learned something!
• Everything changed on the team, and we need to explain.

There are more.

We haven’t discussed the length of your All Hands, and now is a good time. The maximum amount of time is 90 minutes. Frequency? Minimum is once a quarter.

• 90 minutes is a lot of time. In my experience, the average human’s attention span in a meeting like this is 30 minutes, which is why I have the above-suggested agenda. Think of it as three acts. Act 1 sets the table. Act 2 is the heart of the matter — what the team is actually doing. Act 3 brings in the rest of the company — more on that in a moment. Each act gets about 30 minutes. Act 1 runs short unless the building’s on fire, Act 2 always runs long, and Act 3 you can cap.
• Once a quarter is the sweet spot for this meeting. Four times a year. Every month? Overkill and a waste of time. Once a year? Not an All Hands, it’s an Annual Report.

I’m talking timing right now because Act 2’s size is a function of the number of direct reports. Three? They should all have a slot — seven minutes per direct, but they’ll end up using 10. Anything more than three and you’ll need to devise a rotation between directs.

Back to their agenda. You should roughly know what they are going to talk about, but don’t micromanage it. It’s their schtick. If they screw it up, give them feedback.

You’re building the humans who will replace you. All the time. This is one of the many ways you do that.

The Mystery Guest

For Act 3, you want to bring in someone else for a fireside chat. Who? Depends on your team or your company. Start with known folks who are obvious co-conspirators. Folks you personally know with an existing rapport. Write 10 or so questions that you want to ask them, and send them the questions a week before. Warn them that you might go off-script — because you might — and see if they are OK with such vibes.

When you get to the External Speaker portion of the All Hands, sit down next to them and start asking the questions. The most important advice? Listen to their answers. By far, the most interesting bits of this interview are the new things you discover via the conversation.

After you’ve done a handful of familiar folks and have a well-refined set of questions, start asking humans you don’t know. Folks you’ve heard of that the team has worked with, but don’t know. My favorite one? I had the CEO show up once as a mystery guest. Fascinating 30 minutes.

Which reminds me. Tell no one who the speaker will be, except the humans who must know.²

No Q&A?

A controversial take, but an earned one. If I’m doing a talk at a conference, the Q&A portion of the presentation is my favorite. The questions quickly tell me how well I delivered the core messages of my talk. Even the random ones that have very little to do with my talk.

All Hands meetings are a different beast. Yes, it is a series of presentations and, yes, there are core messages delivered, but the large surface area covered in ninety minutes plus the size of the audience usually means questions:

• Feel random, and/or
• Purely serve the agenda of the human asking the question.

However, you must create one more venue for the team to ask questions. Think Slack, your favorite message app, or via staff meetings. Even if you don’t, don’t worry, the important questions will find you.

Entropy Crushing

Being social is work. Especially for engineers. We’d much prefer to be jamming at our desktop. Each time I’ve landed at a new gig where there was no culture of All Hands, I was disappointed by the attendance at first. 50% or worse.

Yes, you can order donuts, and more will show up, but the real draw should be the presentation.

They should leave with the lesson: This is where I will learn.

A regular All Hands meeting is inoculation. You are inoculating your team with quality information. This information will be used to disassemble gossip, rumors, and lies. This information will answer questions before they are asked. This information will remove noise so the human can focus on why they are there — to build.

1. The folks who need the All Hands the most are the ones who are the least able to request it. See, your old guard employees, even in a rapidly growing team, are the best equipped to gather and share signal. This is why when someone new says, “We should do an All Hands,” they react negatively, “Why? That’s a big company meeting, and we’re a small group of high-hustle movers and shakers.” Yes, this meeting is not for the old guard; it’s for everyone who came after them. ↩︎ 
2. While I am preaching consistency, with regard to your External Speaker, I like keeping it a mystery because it will, eventually, give your team more motivation to attend. I wonder who it is this time! ↩︎ 

Welcome, new leader. We’re glad that you are here. Your arrival fills a critical vacancy in our team, and we can’t wait to see what you can do at this company. We’re going to say that we’re not in a hurry and you should take your time, but we’re in a hurry.

Before you arrive, we’re going to tell you what we think needs to be fixed. You should listen to us, but the issue is that we probably don’t know what is broken. Either we’re too busy to notice, or we’re too close to the source material. We wrote the current script, so we’re required to believe it is good. It’s not. It’s a disaster, and it’s breaking, and we need you to investigate, and then to tell us what’s wrong.

Here’s the rub. We’re not going to believe you when you tell us. If that all feels like a trap, it’s not — it’s just senior leadership.

Hi, Rands here. I’m not typically this prescriptive, as every individual, team, and company has different values and culture. Thing is: everything I include in the checklist is a tactic I’ve used at wildly different companies for the past twenty years. This might say more about me than the teams and companies, but they also work.

Recurring 1:1s with Inner Circle

No surprise here. I’ve been preaching 1:1s for years. Within a few weeks, you should have 1:1s with all of your direct reports and your boss. You should also have a sense of what type of 1:1 works for each of them. There are humans who prefer a wandering, casual conversation, and those who want to know precisely what topics will be discussed beforehand.

The goal for this meeting is to establish a consistent weekly meeting that is a safe place to discuss topics of note. These are issues, questions, or discussions where the two of you can seek understanding. These topics can show up as part of casual conversation, but I like to get in the habit of sharing these beforehand with a bit of context as to the intent. I use a 1:1 Slack channel for this, but any medium works; the content is less important than everyone involved knowing this meeting happens every week, no matter what.

Here’s the rub. Your 1:1 list as a senior leader is bigger than direct reports and immediate leadership; your 1:1 list includes the entire ecosystem of humans who support your team in getting the job done.

Who?

Sorry, the list varies wildly depending on company, culture, and that moment in time, but there is an essential and non-obvious set of other humans who require as much investment as your team and your boss. Most of these humans will be names that you just keep hearing. Sarah this. Sarah that. No one is saying, “You should spend time with Sarah,” but Sarah is clearly in the team’s bloodstream, and it’s your job to figure out why.

My default move in the first three months — and it’s an expensive one — is, “Always schedule 1:1 time.” Possible learnings from this meeting include:

• This is a human with some juicy signal about the state of our teams — keep meeting.
• This is a human who has a signal that I have already heard — don’t meet again.
• This is a human whom I sure like, but who doesn’t really have signal — don’t meet again, have lunch occasionally. You never know.

You’ll know it’s working when you find a mystery. I found one on the second weekend at my third start-up. Ryan wasn’t the first engineering leader to raise the topic, but he did ask the question, “How are we promoting engineers fairly?” We weren’t was the unfortunate eventual answer. Promotion was left up to the engineering manager’s discretion, with a meaningless gut check by senior leadership. They still acted like it was twelve people in temporary space, but there were over one hundred engineers, and we were on track to double in the next year.

Extended Staff Meeting

Of course, you’re doing a Staff meeting. Getting all your directs together for the weekly breaking of the professional bread? A quick metrics review followed by a set of team-supplied discussions with a compelling chase of Gossip, Rumors, and Lies. Unlike 1:1s, I’m not going to regurgitate my thoughts on the necessity of Staff meetings.

Here’s the rub: you need another meeting, the Extended Staff Meeting, which you need to have in place by your second month. Required attendees for your Staff meeting are obvious: your direct reports. Maybe you’ll have special guests who are critical support from across the team, and maybe those folks will be regulars. Go for it. No more than ten ¹

Required attendees for your Extended Staff are:

• Everyone we just defined for Staff.
• Every manager in your organization. (Yes, every single one)
• Every leader in your organization — keep reading.

That last bullet is a slippery one, but before I explain how to select these folks, let me explain what is happening in this meeting. Yes, a lot more people than your Staff meeting. Yes, you’ll need to present more than discuss, but this is not your All Hands; this is still a meeting, and discussion is required.

In your 1:1s, you’ve been discovering mysteries, and this venue (and your Staff meeting) is the place to discuss and refine these mysteries. Are we promoting fairly? Do we have a quality issue? Are the robots taking over? The point isn’t to solve the mystery; the point is to explore the mystery. In order for this discussion to be productive, all leaders need to be included.

You can’t have every single person in the Extended Staff (that’s All Hands); you need to draw the line somewhere, but in my experience, a pure manager meeting can turn into a manager-echo-chamber where everyone starts agreeing with each other because of the chain of command. You need someone who is going to say the hard thing, which is why you need a selection of senior leaders from the team. Your most senior engineers? Sure. Longest tenured humans? Maybe. Some easy-to-define and explain slice of leaders who don’t have the management title.

You’ll know it’s working when someone in Extended Staff points out something terrible about one of your mysteries. It’s hard to make these up, but it’s easy to imagine when they show because it’s like getting punched in the face. You are instantly and forever changed by the comment, and, again, it usually shows up from an unexpected someone who many think should not be in the room.

But they are there. And they say it. And what was a mystery is now a critical problem. And it’s your job to fix it.

All Hands

It’s your third month. You have a reliable set of recurring inner circle 1:1s. Your Staff meeting is a weekly event. You’ve had two or three Extended Staff meetings at this point, and now you’re ready for the Main Event, which isn’t actually the Main Event.

Your All Hands includes your entire team, and the agenda for this first one is straightforward:

1. Hi, this is who I am.
2. This is who I’ve spoken with, and this is what I’ve discovered: both good and bad. It’s very enticing to focus on the bad because that is where you need to invest, but highlighting the good gives you credibility points — He has a full awareness of what’s up — which you are going to need later when you start tearing stuff down.
3. And, most importantly, this is what I’m going to do about the bad stuff.

I’m not going to say a lot more about the All Hands because there’s a chapter in the new book. If you already followed my advice on 1:1s, Staff, and Extended Staff, then this meeting is more performance than content. You’ve already clearly identified the critical mysteries, and it’s not the point of this article to define how you might address the issues. This article is about building communication structures, and your All Hands is mostly a one-way report to the team. Be sure to:

• Give them a reason to show up — donuts are a surprisingly cheap way to improve attendance. Also, delicious.
• Keep the presentation tight — practice a lot, practice in front of people who will give you feedback, practice some more.
• When you declare what you’re going to do about it, clearly define when you (or your team) will be following up with status.

Here’s The Rub

Third start-up. I’d been hired as the VP of Engineering. The prior fellow had a rough go at it. Deeply technical, but unable to communicate his vision to his peers and his team. My read was that it ended poorly, and when I arrived, everyone was rattled by his exit.

First VP gig. Prior occupant — it didn’t go well. My instinct. Learn everything, and until you know everything, lie low. When someone asks, “What’s your vision?” tell them, “I’m still learning.”

Month two. The co-founder, who I was sure was the reason I was hired in the first place, pulled me aside, ashen-faced, and told me, “You gotta start talking.”

Me: “Why? I’m still figuring this place out.”

Him: “We’re wondering if we made the right move with you.”

Six. Weeks. The company had been around for seven years at this point. There were 110 engineers and a wildly successful product with a commensurate amount of absolute chaos. I could see potential brokenness, but I was still gathering signal.

I scrambled. The good news is that I had already done everything I described above. Mysteries had turned into heinous problems, and I had vetted solutions with people I was beginning to trust. Got the All Hands on the books, practiced, practiced some more, and then show time. Laughs at the right time. Claps, too. Appropriate solemn silence when I described what was fundamentally broken. A success.

How did I know? Because the CEO walked up to me after the All Hands, grimacing. Uh oh

Him — synthesized: “A good assessment, but I don’t see the problems you describe. I see the problems I can see. You should focus on the problems I can see.”

A front-line manager’s job is to take the time to understand and adapt to the current situation. For a new senior leader, you are the situation. Chances are, your boss and your senior peers are in the middle of it. They are smack dab in the center of the chaos, and while their perspective is relevant, it’s blurred by history and chaos. One of your immense fading advantages as the new senior leader at the table is that you have no history in this current chaos, yet. You have fresh perspective that has not been beaten into submission by the chaos.

It’s no one else’s job but yours to fix what ails your team. No one is going to give you permission.

And you’ll know it’s working when they don’t believe you.

1. More than ten? Time for a reorganization, sorry. ↩︎