Pre-mortem: how this could fail

Find the failure before it happens, then a cheap way to prevent it.

Any plan you are about to commit money or months to.riskdecisionsplanning

Run a pre-mortem on my plan. Imagine it is 12 months from now and the plan has clearly failed.

The plan: <describe what you are going to do, with timeline and budget>
What success would have looked like: <the outcome you want>

Write:
1. Seven distinct reasons it failed, as short past-tense headlines ("We ran out of cash in month 4 because…"). Cover market, execution, money, people, timing and something I probably haven't thought of.
2. For each reason: how likely it is (low/medium/high), how early I would see the warning sign, and what the warning sign looks like.
3. For the three most likely: one cheap action I can take this month to reduce the risk, and one thing I should decide now about when to stop.

Be direct. Do not reassure me. Do not pad with generic risks that apply to every business; every item must reference something specific in my plan.

Replace every <placeholder> with your own details before you send it.

How to use it

1Be specific about the plan. Vague plans get vague failures.
2Rank the list yourself afterwards. The model doesn't know your appetite for risk.
3Run it again in three months with what actually happened.

Reviewed 2026-09-20

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