A field manual for AI-native teams

Sledgehammers and Shit Umbrellas

Nothing changes in a big organisation until somebody hits it with a sledgehammer. Then it rains on the people doing the work, and somebody has to hold the umbrella. AI made building cheap. It made nothing else cheap, so now you need a bigger hammer and a bigger umbrella.

138 lessons in 2 acts · 58 diagrams · 15 appendices of templates to steal · by Simon Stead

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Act 1: the old shit

Two jobs. One very wet team.

Plenty of people in a large organisation know what should change. Very few of them can make it happen. The ones who try get shat on. This book is about both halves of that.

  • Sledgehammer

    The person with enough power to force a decision through.

  • Shit umbrella

    The person who stands between the team and the backlash, so the team can keep working.

  • Hand grenade

    If nobody will swing the hammer for you, make something so hard to ignore that the decision has to be made.

  • HiPPO

    The most senior person in the room, whose opinion wins by default, whatever the data says. Can be your sledgehammer or your wall. Term usually credited to Avinash Kaushik.

You need both. A hammer with no umbrella burns teams out. An umbrella with no hammer protects a team that never ships anything.

From the introduction

  • Most "lessons learned" sessions are a hunt for a name, with sandwiches.

    Lesson 5: Every good delivery manager is a shit umbrella

  • RAG ratings exist so nobody ever has to write "this is fucked" in a sentence.

    Lesson 53: What the fuck is senior leadership for?

  • So a mullet, yes. A wig, never.

    Lesson 56: How to lie to stakeholders

  • You wouldn't run a wake like a stag do. Stop running your retros like that.

    Lesson 52: Pick the retro for the shit that needs shifting

Act 2: the new shit

Building got cheap. Nothing else did.

The decisions, the politics, the procurement and the HiPPO's diary all run at the same speed they always did, so now they're the whole bottleneck instead of most of it.

A ring of seven lifecycle stages, insight, research, analysis, product, build, release and measure and learn, around one room holding a small T-shaped team, the person who decides and agents holding the pen, with an umbrella keeping the shit off the top
The whole book on one page. The same lifecycle good teams always had, in one room, with the machine typing. And an umbrella over it.

Same lifecycle, different shape

Every good team has always gone round the same loop: find out what people need, decide what to build, build it, release it, and see whether it worked. None of that has changed. What AI changed is the shape. The stages used to be a relay, months long, with a document passed at every handover and a bit lost each time. Now they can happen together, in hours, in one room, with the people who know and the person who decides, while the agents do the typing.

From the book on one page

  1. Lesson 91

    Every handover leaks

    Every handover is someone summarising for someone who wasn't in the room, and a summary is a lossy file format. The why goes first, then the edge case, then whatever the client said in the lift.

  2. Lesson 93

    Mob delivery

    Put everyone in the room, stakeholders included, and let the machine hold the pen. Run it like a show: keep the method moving behind the scenes, and keep reminding everyone it's only code.

  3. Lesson 105

    Agents flag, humans decide

    Flag-and-stop turns those guesses into hands up. Every "autonomous agent" demo skips this, because "it stopped and asked a question" makes a shit demo. It makes a very good Tuesday.

  4. Lesson 127

    Sell the dish, not the kitchen rota

    Nobody books a restaurant by hiring two chefs and a kitchen porter for three hours and hoping dinner happens. You read a menu. It has a dish, a price and roughly how long it'll take. How many people are in the kitchen is the kitchen's business.

Who it's for

The people doing the work, and the curious.

Consultants, delivery managers, product people and engineers who've just been given a pass, a laptop, an AI licence nobody's worked out how to govern and a desk by the printer, and have no idea who to talk to first.

It's also for the curious outsider. If you run a legal team, a ward or a board, and you want to know what the best teams actually do and what AI is doing to them, you're welcome here. You don't need to write code. Every technical word is explained the first time it turns up, and the glossary has 176 more, some of them rude.

What you'll be able to do

  • Find the person who can force a decision through, and protect the team from the fallout when they do.
  • Get decisions made in the room, with the thing being decided on the screen, instead of five days later by email.
  • Run a small team that ships, and keep it together.
  • Work with AI agents without handing them the decisions.
  • Sell the work as outcomes, not hours.

Inside the book

Built like a handbook, read like a war story.

Each lesson stands alone. Read one in the 10 minutes before a meeting you're dreading. If you bought this book for the robots, start at Part 4. I won't be offended. I'll be a bit offended.

Lessons
138
Diagrams
58
Parts
10
Appendices
15

Act 1 The old shit

  1. 7

    The kit

    Before you start: who swings, who shields, and how much shit is about to land on you.

  2. 27

    Beginnings

    The first weeks, when you still don't know where the toilets are and everyone is deciding whether you're useful or just another consultant with a deck.

  3. 45

    Middles

    The long, muddy middle, where the novelty's gone and the steering committee hasn't. Most transformations die here, usually in a RAID log nobody reads.

  4. 5

    Ends

    Handing over, saying goodbye, and the email 6 months later that tells you whether any of it stuck or whether they switched it all back the week you left.

Act 2 The new shit

  1. 12

    Same shit, faster

    The machine builds in an afternoon what used to take a quarter. The steering committee still meets monthly. Guess which one sets the pace.

  2. 15

    The robots read the repo

    How an agentic team actually works. The agents read everything you wrote down, which is a problem, because you didn't write anything down. The humans still make every decision, even the ones they'd rather an agent took the blame for.

  3. 12

    Meatbags still required

    What happens to the people. Somebody still has to know when the machine is talking shit, and that somebody needs hiring, training, protecting and, for about a month, talking down off a ledge.

  4. 8

    Selling the robots

    Rate cards, tenders, contracts and governance, all designed for a world where building was slow. Charging by the day when you're six times faster is a great way to get paid a sixth as much.

  5. 4

    On the call

    Remote, hybrid, and what 2020 did to the work and to the people doing it. Cameras optional. Shit wifi guaranteed.

  6. 3

    Small organisations

    Startups, side projects and being your own sledgehammer, sometimes right up until the money runs out. Nobody holds an umbrella over you when it's your own shit.

  1. 15

    Appendices

    Worksheets and templates to copy, print, scribble on and leave lying around in meeting rooms. Change them. A template filled in perfectly and used by nobody is still shit. If one of these ever becomes a mandatory process with its own governance board, burn it.

Things you'll find yourself saying

  • The unit of delivery is the team.
  • Building is cheap. Deciding is expensive.
  • If it doesn't end with an artefact, it's not a workshop.
  • If the people in the room can't decide, don't hold the workshop.
  • Calm core, wild edges.
  • You only get called when it's on fire.
  • The incumbents aren't stupid. They're scared.
  • Your stakeholders might be your users.
  • Every handover is a photocopy of a photocopy.
  • That's a nice problem to have.
  • Name teams after the people they serve.
  • Coffee is cheaper than shouting.
  • The speed is fifteen years old.
  • Frameworks are rafts.

Every lesson has the same shape

  1. A story, usually one where I got it wrong
  2. The lesson, in one sentence
  3. Why it works, with the research where there is some
  4. Your move, steps to take straight away
  5. When it doesn't apply, because nothing works everywhere

The diagrams

Draw it, and the argument usually settles itself.

9 of the 58 diagrams in the book, from a weather forecast for shit to a bit of category theory for people who hated maths. Tap one to enlarge it.

Read 2 lessons free

Try before you swing.

One from each act. The whole lesson, story, swearing and all.

Act 1 · Lesson 5

Every good delivery manager is a shit umbrella

Take the backlash yourself, so the team keeps the nerve to move fast.

Read the lesson
Act 2 · Lesson 91

Every handover leaks

The lifecycle stays the same, but every handover between its stages loses something. Do the stages together, with the people who know, and there's nothing to hand over.

Read the lesson

Get the book

Pick your weapon.

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  • All 138 lessons, 58 diagrams and 15 appendices
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Paperback

£24.99 + postage

  • Printed on demand in the UK
  • Diagrams in full colour
  • Worksheets you can scribble on
  • Something to lend the HiPPO

The mailing list

Get the free lessons, and hear when it's out.

Occasional emails. The odd lesson that didn't make the cut. No more than that.

The author

Simon Stead

Simon works where product, engineering and transformation strategy meet, which is usually where the problems are. He runs large enterprise engagements, talks to users himself, and does his own service design and user research. He learned the trade in a digital unit set up by people from the government digital movement, and has since worked with national broadcasters, health services, banks, regulators and retailers.

He builds his own tools, too. His reports have their own design system and Storybook component library, and a few scripts turn the same React components into websites, PDFs and slide decks from one repo. Nothing gets copied into Google Slides. The LCR Summit app for the Liverpool City Region is one example. He has a first-class degree in mathematics, which explains the diagrams, and the category theory.

steadtec.com →

Questions

Asked, answered.

Who is it for?

Consultants, delivery managers, product people and engineers who walk into a large organisation and quietly wonder where on earth to start. Also the people who hire them, and anyone curious about what the best teams actually do now that the machine does the typing.

Do I need to be technical?

No. Where the book uses a technical word, it explains it, and the glossary at the back has 176 entries for the rest. It borrows from contracts where it can: a proposed change is a redline, and merging it is signing the clean copy.

Is it a book about AI?

Half of it. Act 1 is the old shit: politics, meetings, stakeholders and teams, which haven't been upgraded. Act 2 is the new shit: what changes when building is cheap, how an agentic team works, what happens to the people and how you sell it. If you bought it for the robots, start at Part 4.

Is it a methodology?

No. It borrows from Scrum, Kanban, Shape Up, XP, Team Topologies and content design, and treats every one of them as a raft: something to cross the river on, then put down.

Is it finished?

It's in late draft. Buying the PDF now gets you the current edition and every update until the final one.

What format is the PDF?

A DRM-free PDF with every diagram, worksheet and template. Read it on anything. Print the worksheets.

Where does the paperback ship?

It's printed on demand and posted from the UK, with delivery to the UK, Ireland, Europe, North America and Australasia.

Is it really that sweary?

"Shit" is a technical term in this book. "Fuck" turns up when it's the honest word, which in a steering committee is more often than you'd hope.