Updated: 31 October 2026

Run a pre-mortem on your plan

This prompt imagines that your plan has completely failed at a future date and works backwards to find likely causes and how to prevent them.

text-pre-mortem — chatgpt — 53 words

Imagine it is [TIME] from now and my plan has completely failed.

The plan: [PLAN]
Who is involved: [PEOPLE]
Key assumptions: [ASSUMPTIONS]

List the ten most likely reasons it failed, ranked by probability and impact. For each, suggest an early warning sign and one action I can take now to reduce the risk.

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Do it before you commit money or announce the plan, while changing course is still cheap.

Get a better result

What you will get

Ten reasons your plan could fail, ranked by how likely and how damaging each one is, each with an early warning sign and one thing you can do now to reduce the risk.

Common mistake

The reasons are generic, like “poor planning”.

Fix: Give real numbers and names in the plan and assumptions, such as the budget and who owns each part, so the failures are specific.

Also watch for

Your key assumptions are left blank. Write down what must be true for the plan to work, like “we sign 10 customers by March”. The best failure reasons come from these.
Every risk gets an expensive fix. Ask for actions that cost under a day of work or a small amount of money, and mark the ones you can do this week.

Try a variation: run a pre-parade

Flip it: imagine the plan was a huge success and ask for the ten reasons why, then check which of them you are actually doing.

Still not right? Reply with this

My team added these failures that were not on the list: [ADDITIONS]. Rerun the pre-mortem with them included and rank the top five by likelihood.