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#20 Courage (Part 2 of 2) — Making It Cheap to Try

courage Sep 09, 2026

Last week I made the case that most good ideas in established companies aren't rejected. They're slowed until the energy drains out of them, because an attempt costs too much to make casually.

The obvious conclusion is to make everything small. Run pilots. Keep it reversible. Start on Monday.

That's half right, and the wrong half causes real damage. So let me start this edition by arguing against the advice I'm about to give.

(New here? This stands on its own, but the diagnosis behind it was last week's edition on why nothing starts. And the Digital Leader Canvas, the free companion to this series, is here.)


Reading time: 7 minutes. If you take one thing from this: "make everything small" is only half an answer, because some AI changes only work whole, and a hundred pilots can be a way of avoiding one decision. Ahead: four rules that lower the cost of trying, the Disney move for keeping critics in the right seat, and which instrument really builds courage in a team, which is rare...

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#19 Courage (Part 1 of 2) — Why Nothing Starts

courage Sep 04, 2026

"We should be careful about starting something like this."

Some version of that sentence reaches me several times a year, and it's almost never about something large. The most recent case was 360-degree feedback: one department, a few weeks, software optional, entirely reversible.

Careful about a feedback pilot.

Nobody involved was blocking anything, and I want to be clear about that before I use it as an example. The caution was reasonable by the standards of the place. In organisations like that, nothing stays small: every initiative becomes a proper undertaking, a boulder to be set in motion. Capacity is thin to begin with, so anything new has to queue. By the time it reaches the front, the energy that started it has drained away. That's how most initiatives die in established companies. Not refused. Slowed until nobody quite remembers why they mattered.

Most conversations about AI in organisations are about capability: which tools, which use cases, which skills, what it costs, ...

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