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How to ThinkIn the Age of AI

5-15 minute pre-mortem before committing to any project…

Before committing to any significant project plan, conduct a 5-15 minute pre-mortem by assuming failure has occurred and listing 3-5 specific failure causes to surface risks that forward-looking analysis systematically misses.

When This Fires

  • Before committing to a project timeline, budget, or scope
  • Before making irreversible resource allocation decisions
  • When a plan feels "solid" but you want to stress-test it
  • Complements Start project estimates with reference class forecasting… (reference class forecasting) with the risk-identification dimension of estimation

Common Failure Mode

Perfunctory pre-mortem: listing obvious risks ("might run out of time," "scope might creep") that don't surface genuinely new information. The pre-mortem should produce at least one failure cause that surprises you — something you hadn't considered in forward planning. If nothing surprises you, you're not doing it honestly.

The Protocol

(1) Set a timer for 5-15 minutes (scale with project significance). (2) State the premise: "It is [future date]. This project has failed. What happened?" (3) Write 3-5 specific failure causes. Each should be concrete: not "timeline issues" but "the data migration took 3 weeks instead of 1 because we discovered legacy format incompatibilities." (4) For each cause, ask: "Is this preventable? What would we need to do now to prevent or mitigate it?" (5) Incorporate the most likely preventive actions into the project plan. Adjust the timeline and resource allocation based on the risks the pre-mortem surfaced. If the adjusted plan is unacceptable, that's critical information — better to know before committing than after.