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Automation Squad
Hand to your teamWritten for Claude or ChatGPT

Run a pre-mortem before I commit to something big

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

Asking a model for risks gets a hedged list nobody acts on, because listing risks and inhabiting a failure are different cognitive tasks. Forcing three separate committed accounts surfaces different failure modes each time, and lens 3 does the uncomfortable work — most failures were foreseen by somebody whose warning didn't land, which is a fixable organisational problem rather than an unlucky one.

The prompt

We're about to commit to this: [THE DECISION, AND WHAT WE'RE COMMITTING — money, months, headcount, reputation]

Context you need: [TIMELINE, BUDGET, WHO'S INVOLVED, WHAT'S ALREADY BEEN PROMISED TO WHOM]

It's [PICK A DATE, 6-12 MONTHS OUT]. This failed. Not "underperformed" — failed, visibly, in a way people are talking about.

Write the story of how, three times over, from three different vantage points. Do them one at a time and fully commit to each before moving on.

LENS 1 — THE PERSON WHO DID THE WORK.
It failed because of something about execution: the thing was harder than scoped, a dependency never arrived, the team it needed was busy, the quality bar was silently lowered. Write their account.

LENS 2 — THE CUSTOMER OR USER.
It failed because it was built and nobody wanted it, or they wanted it and couldn't get to it, or they got to it and it didn't fit how they actually work. Write their account. They are not obliged to be reasonable.

LENS 3 — THE PERSON WHO WARNED US.
Someone had doubts and either didn't voice them or voiced them and was talked round. Write what they saw, and — this matters — why it didn't land at the time. Was it timing, seniority, framing, or because we'd already announced it?

Then synthesise:
- Which of the three stories is most likely, and why
- The single earliest observable signal that we're heading into that one — something we could see in weeks, not months
- The one change we could make now that would most reduce the chance of it
- The thing we should decide NOW that we'll otherwise decide badly under pressure later

Do not reassure me at the end. If lens 3 is the most likely, say that plainly — it usually is, and it's the only one that was preventable by talking.

Copy it, paste it, run it. Nothing here is gated.

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Written for Claude or ChatGPT as of August 2026. Models change — if this stops working the way it should, that is worth telling us about.