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.
Lays out a decision as genuine options with their costs and risks, names the recommendation, and states what would change your mind.
Works with Claude, ChatGPTUpdated 2026-09-27
Use this before a decision that others need to weigh in on. Most decision papers present one real option and two straw men; this is built to make the alternatives genuine and the assumptions visible.
Write the memo in six sections.
1. THE QUESTIONTell 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.
Imagines the plan has failed, works out the most likely reasons why, and turns the credible ones into things to check or change now.
Writes the message explaining a decision: what was decided, why, what it means for the people reading it, and what is not changing.
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.