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Book club guide

Open and Async is a book about how teams actually work — so the best way to read it is with the people you work with. This is a set of questions, exercises, and arguments to run a discussion, whether you’re a team of eight or a team of one.

Read a chapter, then use these prompts to turn it into an honest conversation about how your team actually works — what you’re great at, what you’re quietly tolerating, and the one change worth trying next. That’s when a book stops being ideas on a page and starts changing how you work. Free to use with your team; steal what’s useful.

How to use this guide

Pick a track:

  • Quick track — one session, about 60–90 minutes. Good for a leadership offsite, a lunch-and-learn, or a team that wants the big ideas in a single sitting.
  • Full track — nine sessions, one per part of the book. A part a week is roughly a quarter; a part a fortnight, roughly half a year. Read the part, then meet (or thread — see below).

Three to eight people is the sweet spot. Bigger than that, split into pods and compare notes. Reading solo? Treat the questions as journaling prompts, argue both sides of each debate on paper, and run the “try it” exercises for real at work.

Quick track — one session

Ninety minutes, three moves: sit with the big ideas, take stock of where you are, and commit to one change.

1. Three big ideas

2. Talk it through

  • If you couldn’t measure hours or online status, how would you know this team is doing well?
  • What’s the most important thing we decided last month — and could a new hire find it, with the reasoning, in under five minutes?
  • Which recurring meeting would we not miss if it became a document and a comment thread?
  • Where does a small, hidden problem tend to grow expensive before anyone surfaces it?
  • What’s one office-era habit we’ve faithfully recreated online that we’d never design from scratch today?
  • Where does disagreement go on this team — into the open, or into DMs?

3. Where are we now?

Rate each statement 1 (rarely true of us) to 5 (almost always). Then spend your time on the gaps, not the number.

  1. Our decisions live at a URL anyone on the team can find and cite later.
  2. We default to writing; a meeting is an escalation, not the first move.
  3. Progress is visible without anyone having to ask for a status update.
  4. We measure what people ship, not how long they’re online.
  5. When something’s broken, we surface it early and loudly — no shame in pulling the cord.
  6. The unwritten rules a new hire needs are actually written down.

4. Commit to one thing

Before you close, each person names one change to try this week — one meeting turned into a doc, one answer written down, one decision given a URL. Put them where the group can see them, and check back next time. Small and done beats ambitious and theoretical.

Full track — nine sessions

One block per part of the book. Each has the same shape: an anchor line to open on, questions to discuss, a split for managers and individual contributors, a debate to argue both sides of, and one thing to try before you meet again.

Session I

Foundations and definitions

“Async is the operating system; remote is the hardware.”

Discuss

  • Where has our team confused “working from home” with actually working remotely — the same office habits, just moved onto Zoom?
  • Walk through a normal week: which of our rituals quietly assume everyone’s awake at the same time? What breaks when someone joins from another time zone?
  • Where do we work in the open but still default to meetings — or try to go async without actually sharing our work? What does that half-measure cost us?

Split the room

For managers

Name one process you own that assumes co-location. What would it look like rebuilt for a team that’s never in the same room?

For individual contributors

Pick one thing you did silently last week. How could you have made it visible without being asked?

Debate

“We’re already remote — we use Slack and Zoom all day.” Argue that that’s enough. Then argue it’s exactly the trap the book warns about.

Try it

Map your team’s default channel for five situations — a decision, a status update, a quick question, a crisis, an FYI. Which are still findable and searchable a month later? Optional: run triage_sync_vs_async from the companion tools.

Sessions

Session II

The case for open and async

“The real risk isn’t openness; it’s opacity.”

Discuss

  • When did two of us last solve the same problem separately because neither could see the other’s work? What did that duplication cost?
  • If location stopped mattering, who could we hire — or keep — that we can’t today? And who have we already lost by pretending it does?
  • Which of our decisions live only in someone’s memory or a closed meeting? What happens when that person is out, or leaves?

Split the room

For managers

What’s one decision you made privately this quarter that would have been stronger with the reasoning in the open?

For individual contributors

Where would working louder — sharing progress and risks early — have caught a wrong turn three weeks sooner?

Debate

“Working in the open just invites noise and second-guessing.” Make the case for keeping things private — then make the book’s case that opacity is the bigger risk.

Try it

Take a recent decision and write the one-paragraph “why” behind it, as if a teammate in another time zone had to understand it cold. Optional: run draft_decision_doc from the companion tools.

Sessions

Session III

Core principles and mental models

“Async isn’t slow; it’s choosing your interrupts.”

Discuss

  • Be honest: where does our team reward looking busy over shipping outcomes — green dots, instant replies, a calendar with no white space?
  • The book calls interruptions a tax that steals hours, not minutes. When did you last get a real four-hour block of focus? What ate it?
  • If you read team morale as a gauge — an early warning, not a nice-to-have — what would ours be reading right now?

Split the room

For managers

If you couldn’t see hours or online status, what would you measure instead — and could you defend it to your own boss?

For individual contributors

What’s one piece of “performance theater” you do because you think you’re being watched? What would you stop if you trusted you wouldn’t be judged for it?

Debate

“If I can’t see people working, how do I know they are?” Argue the surveillance side. Then argue why the book says that question is the actual problem.

Try it

For one week, everyone tracks the single most valuable thing they shipped each day — not hours, not activity. Compare notes at the next session.

Sessions

Session IV

Working in the open

“If it’s not written down, it wasn’t decided.”

Discuss

  • Which of our decisions, processes, or docs don’t have a URL? How far are we from losing them to one departure or one retention policy?
  • Who’s the person everyone DMs the same three questions? What would it take to write those answers down once, where people can actually find them?
  • When did we last sit on a small problem — hoping it would sort itself out — until it got expensive? What made surfacing it feel costly at the time?

Split the room

For managers

Do you reward the people who surface bad news early, or the ones who quietly fix things and never mention the risk? What does your team believe the answer is?

For individual contributors

What are you working on right now that no one would know about unless they asked? Where would you post a progress update so they wouldn’t have to?

Debate

“If I share every rough draft and dead end, I’ll just look disorganized.” Argue it. Then argue why an ugly working URL beats a beautiful deck.

Try it

Take the three questions people ask you most. Write each answer once, put it somewhere linkable, and send the link next time instead of retyping it.

Sessions

Session V

Asynchronous communications

“Async is a default, not a dogma.”

Discuss

  • Which of our recurring meetings could be a document plus a comment thread? What’s actually keeping it on the calendar?
  • How do we decide what belongs in chat, what belongs in a tracked issue, and what belongs in email — and where does that blur, so we relitigate Monday’s decision on Tuesday because nobody can find it?
  • “Got a minute?” gets called anxiety in three words. What’s our culture around interrupting each other, and who pays for it?

Split the room

For managers

What’s a meeting you own that mostly relays information a transparent system could carry? What would you have to make visible to cancel it?

For individual contributors

Next time you’re about to DM “got a minute?”, what could you write instead so the answer helps everyone and doesn’t break their focus?

Debate

“Async is just slower — sometimes you need an answer now.” Argue it. Then argue the book’s line: async is the default, and sync is the escalation you reach for on purpose.

Try it

Take your next “let’s hop on a call” and turn it into a written artifact with a clear owner and a decision deadline instead. Optional: run convert_meeting_to_async from the companion tools.

Sessions

Session VI

Adopting and transitioning

“Tools amplify culture; they don’t create it.”

Discuss

  • Where have we adopted a new tool and expected the behavior to follow — and it just didn’t?
  • Change usually dies quietly. Where does resistance on our team look like agreement — nodding in the meeting, nothing different afterward?
  • What’s one legacy office habit we’ve recreated online that we’d never design from scratch today?

Split the room

For managers

Are you asking your team to work in a way you don’t model yourself? Where’s the gap between what you ask for and what you actually do in the open?

For individual contributors

You don’t need a mandate to start. What’s one open or async practice you could adopt this week that would make others curious how you did it?

Debate

“Our culture just isn’t ready for this.” Argue the go-slow case. Then argue the book’s: stop convincing skeptics, and start making them jealous.

Try it

Pick one meeting-heavy workflow and rebuild it from first principles, as if the team had never had an office. Compare it to how you do it today.

Sessions

Session VII

Leadership

“Control doesn’t scale; trust does.”

Discuss

  • Who here leads through influence rather than a title — and do we actually recognize it as leadership, or only reward the org chart?
  • Which of our “decisions” are really just vibes from a meeting nobody can cite — findable at a URL, or gone with whoever was in the room?
  • Where does dissent go when someone on our team disagrees — into the open, or into DMs and side channels?

Split the room

For managers

Look at your last month of 1:1s. Were they status updates that belong in an issue, or the coaching and hard conversations only real-time can carry?

For individual contributors

Leadership isn’t the org chart. Where could you make a decision legible, take a DRI role, or document the “why” so the whole team moves faster?

Debate

“Some things a leader just needs to handle in the room.” Argue it. Then argue why charm doesn’t commit to the repo — and what’s lost when leadership is a performance.

Try it

Write one decision you own as a short doc: what you decided, why, and what would change your mind. Post it where your team can comment. Optional: run draft_decision_doc from the companion tools.

Sessions

Session VIII

Team health, culture, and sustainability

“Culture is whatever you tolerate twice.”

Discuss

  • What have we tolerated twice that’s now just “how things are” here? Is it what we’d choose on purpose?
  • Whose work went unnoticed here recently? What might that quietly cost us later — and whose job is it to notice?
  • Where has a disagreement here festered instead of getting resolved? What were the early signs — and did we move it to a real conversation in time?

Split the room

For managers

What’s one unwritten rule new hires here absorb by osmosis? What would it take to write it down so onboarding doesn’t depend on luck?

For individual contributors

Your growth won’t manage itself. When did you last run a “career retro” or document a win? What would you put in one this week?

Debate

“Fun and culture stuff is nice, but it’s not the real work.” Argue it. Then argue the book’s line: fun is infrastructure, and social capital is conflict insurance.

Try it

Each person names one teammate whose recent work made their own job easier — and tells them, specifically, somewhere the whole group can see it.

Sessions

Session IX

Looking forward

“AI didn’t break async work. It vindicated it.”

Discuss

  • Where would an AI agent get stuck in our workflow today — a vague issue, an undocumented decision, a thin test suite? And what does that gap reveal about how we onboard humans, too?
  • Where has writing a clear request to an AI forced you to actually define the problem first — and where did it expose thinking that was fuzzier than you realized?
  • The book warns: outsource your thinking and you outsource yourself. Where’s the line for us between AI sharpening judgment and quietly replacing it?

Split the room

For managers

Would you hand an AI agent an issue from your backlog exactly as it’s written? If not, what’s missing — and would a brand-new human hire hit the same wall?

For individual contributors

What’s one task you’d delegate to an AI teammate through an issue → branch → pull request loop? What context would it need that isn’t written down yet?

Debate

“AI changes everything about how we work.” Argue it. Then argue the book’s counter: the clarity an AI needs is the same clarity a teammate in Nairobi needs at 2 a.m.

Try it

Take a real task and write it up as an issue clear enough that either a new teammate or an AI agent could run with it, no meeting required. If you can’t, that’s the gap to close.

Sessions

Facilitator notes

Run the book club the way the book says to work: async by default, sync as escalation. There’s a nice recursion in reading a book about async collaboration asynchronously — you’ll feel the ideas before you finish arguing about them.

Async format (recommended)

Post the session’s questions in a shared doc or an issue thread at the start of the week. Everyone reads the part and answers in writing, on their own schedule, then replies to each other in the thread. Hold a short live call only if a thread gets stuck or a debate needs some heat — the meeting is the point of escalation, not the default. You’ll get more voices, better answers, and a searchable record you can point the next new hire at.

Live format

45–60 minutes a session. Rotate the facilitator each time. Open on the anchor line, work the discussion questions, split the room for the manager/IC prompts, run the debate with someone assigned to each side, and don’t leave without agreeing on the “try it.”

Ground rules

  • Disagree in writing and in the open — that’s the whole point.
  • Cite the book (a chapter, a line) so it’s a discussion, not a debate about who remembers what.
  • Keep it about your team and your work, not abstractions.
  • The debates have no “correct” side. Arguing the position you don’t hold is where the learning is.

Companion resources

  • The quotes wall — every anchor line above is a shareable card. Drop one at the top of a session thread.
  • The companion tools — a free server that puts the book’s method (drafting a decision doc, running an async standup, pressure-testing a status update, settling sync vs. async) right in your editor. Handy for the “try it” exercises, entirely optional.
  • The key ideas — the short version of what each part is about, if you’re deciding where to start.

Everyone needs a copy

The best sessions happen when everyone shows up having read the same chapter. Get a copy for every seat at the table — or a stack for the whole team.

Get the book Copies for the team