Write a decision memo that shows the real options
Lays out a decision as genuine options with their costs and risks, names the recommendation, and states what would change your mind.
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
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.
Assume it is a year from now and the plan has clearly failed. Work through four sections.
1. HOW IT FAILEDTell us who you are and all 50 prompts open up, with a PDF of the whole library sent to your inbox.
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Lays out a decision as genuine options with their costs and risks, names the recommendation, and states what would change your mind.
Finds the assumptions a forecast rests on, tests which ones it cannot survive being wrong about, and says what to watch weekly.
New prompts as they go up, plus founder essays on shipping AI systems. ~2 emails / month.
Prompts get you started. If you want this wired into how your team actually works, see what we do.