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This explains how to use a “premortem” prompt with AI—telling it your plan already failed six months later—to force it to list failure scenarios and warning signs. It then ranks the most likely and dangerous failures, reveals hidden assumptions, and suggests plan adjustments.
- Asking AI "is this plan solid?" produces biased cheerleading because it's trained to be affirming, not critical
- The fix is a "premortem" prompt: telling the AI the plan already failed six months from now and asking it to explain why, which surfaces failure scenarios and early warning signs
- Kahneman considers premortems his top decision-making tool, and companies like Google, Goldman Sachs, and P&G use them before major launches
- A follow-up synthesis step has the AI rank the most likely failures, name the biggest hidden assumption, and rewrite the plan to close those gaps