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Pre-Mortem on a Strategic Bet
Prompt
The bet: {{STRATEGIC_BET}}
Why we believe it will work: {{ASSUMPTIONS}}
Who owns the outcome (role only): {{OWNER_ROLE}}
Risks we already know about: {{KNOWN_RISKS}}
Produce:
1. Eight distinct reasons it failed. Spread them across market, customers, execution, people, money and timing. Do not repeat the known risks unless you can show a way they would be worse than expected.
2. For each reason, a sentence on the earliest warning sign a leader would see, and which role would see it first.
3. The three reasons that are both most likely and hardest to reverse, with a one-line explanation of why you ranked them that way.
4. For those three, one action to take now that is cheap, and one tripwire: a specific signal at which we pause and rethink.
5. The assumption in my list that looks weakest, and a quick way to test it this month.
Write in plain, direct sentences. Mark any reason that depends on facts I did not give you with [ASSUMES]. Output as a table for items 1 and 2, then short paragraphs for the rest.
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About this prompt
“Pre-Mortem on a Strategic Bet” is a free prompt for ChatGPT in the Reasoning & Problem-Solving category, 209 words long, added to The Prompt Index on November 11, 2026 by The Prompt Index. Copy it with the button above, paste it into ChatGPT or any other AI chat assistant, and send it.
It has 5 placeholders to fill in first:
{{REVIEW_DATE}}, {{STRATEGIC_BET}}, {{ASSUMPTIONS}}, {{OWNER_ROLE}}, {{KNOWN_RISKS}}.
Use the “Customize this prompt” fields to personalise it before you copy.
Recommended models: ChatGPT, Claude, Gemini.
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