Hand to your teamWritten for Claude or ChatGPT
Turn something that went wrong into a checklist that stops it recurring
Founder, Automation Squad
Most post-mortems produce a narrative and a resolution to be more careful, neither of which survives a busy week. The three constraints in section 4 are doing the real work — a checklist item you can answer 'yes' to out of habit isn't a control, and section 6 exists because the dangerous thing about any checklist is the coverage people assume it has.
The prompt
Something went wrong. I want a checklist out of it, not a feeling about it. What happened: [THE FACTS, IN ORDER, WITHOUT DEFENDING ANYONE] What it cost: [TIME, MONEY, TRUST, A CLIENT — be specific] When we first could have caught it: [YOUR BEST GUESS] Work through this: 1. THE TIMELINE. Reconstruct it as a sequence of decision points, not a story. At each point, note what was known at the time — not what we know now. Hindsight contaminates every post-mortem and I want it kept out of this one. 2. THE EARLIEST CHEAP CATCH. Find the first moment where a five-minute check would have surfaced the problem. Not the first moment something was wrong — the first moment it was findable at low cost. 3. WHY THE CHECK WASN'T THERE. Pick one: nobody thought of it, someone thought of it and it was skipped for speed, it existed but was ignored, or it existed and passed anyway. These have completely different fixes and people conflate them constantly. 4. THE CHECKLIST. Now write it. Every item must be: - Phrased as a yes/no question with an unambiguous answer - Answerable in under two minutes - Impossible to answer "yes" to by habit without actually looking Cut anything that fails those three tests. A ten-item checklist nobody completes is worse than three items they do. 5. WHERE IT LIVES AND WHO RUNS IT. A checklist without an owner and a trigger is a document. Name both. 6. WHAT THIS WON'T CATCH. Be explicit. A checklist creates a feeling of coverage, and the gap between what it actually covers and what people assume it covers is where the next incident comes from.
Copy it, paste it, run it. Nothing here is gated.
More for the same job
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.
