Leadership & StrategyAdvanced

Run a pre-mortem on a plan before you commit

Imagines the plan has failed, works out the most likely reasons why, and turns the credible ones into things to check or change now.

Works with Claude, ChatGPTUpdated 2026-09-27

When to use it

Use this after a plan is agreed but before money or people are committed. Teams are bad at criticising a plan they have just agreed to; asking why it failed, as if it already had, gets the concerns out while they can still be acted on.

Excerpt
Assume it is a year from now and the plan has clearly failed. Work through four sections.
1. HOW IT FAILED

Unlock the full prompt

Tell us who you are and all 50 prompts open up, with a PDF of the whole library sent to your inbox.

This opens all 50 prompts, emails you the PDF, and lets us follow up once. No newsletter signup, and we do not share your details.

Related prompts

Browse all 50 prompts

Get new prompts as we publish them

New prompts as they go up, plus founder essays on shipping AI systems. ~2 emails / month.

One-click unsubscribe. We never share your email.

Prompts get you started. If you want this wired into how your team actually works, see what we do.