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How to ThinkIn the Age of AI

Reconstruct the information environment from records…

Before evaluating any past decision, reconstruct the information environment that existed at decision time using contemporaneous records rather than memory, then evaluate the decision against that environment only.

When This Fires

  • During decision reviews, retrospectives, or post-mortems
  • When evaluating whether a past decision was "good" or "bad"
  • When someone is being blamed for a decision that produced a bad outcome
  • Any retrospective evaluation where outcome knowledge might contaminate reasoning assessment

Common Failure Mode

Reconstructing from memory rather than records: "I remember we knew about the risk." Check the records — was the risk documented at decision time? Memory says yes (because you know the outcome); records might say no. Records are the ground truth; memory is the reconstructed narrative.

The Protocol

Before evaluating any past decision: (1) Gather contemporaneous records from the decision period: emails, messages, documents, meeting notes, decision records. (2) Reconstruct the information environment: what was known, what was uncertain, what was unknowable at that time? (3) Evaluate: given only the information available at decision time, was the reasoning sound? Was the confidence appropriate? Were alternatives adequately considered? (4) Only after this evaluation: introduce outcome information. The gap between "good reasoning given available information" and "bad outcome" reveals luck, not poor judgment.