Coaching practices for How to Be Better Calibrated

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Does this sound like the set of challenges you might be facing?

  • I make calls about how things will go all the time, but I never write them down or check them after
  • There’s one area I consider myself an expert in, and that’s exactly where I’m most stubbornly sure and most often wrong
  • My real decisions take months to resolve and matter too much for me to score them honestly, so I never get clean reps
  • When I say I’m eighty percent sure I genuinely don’t know if that means anything
  • I make calls all the time but I never write them down or check them later, so my confidence is just a feeling that floats free

Practices that may help

  1. Calibration Training
    Calibration training teaches you to match your stated confidence levels to your actual accuracy: if you say "70% confident," roughly 70% of those claims should turn out to be correct. Tetlock’s forecasting research and probability training studies show calibration is trainable with practice and feedback — the evidence here is specific and replicable.
  2. Score your own past predictions to calibrate your outside-view use
    Keep a forecast log and score it — you cannot improve calibration without feedback on where you were over- or under-confident.
    The Outside View
  3. Identify the specific domains where you are most overconfident
    Calibration is domain-specific — find where your confidence most exceeds your accuracy.
    Calibration Training
  4. Build calibration reps with low-stakes trivia and almanac questions
    Use factual trivia questions as a practice ground for calibration — outcomes resolve immediately and the stakes are zero.
    Calibration Training
  5. Practice calibration by tracking your confidence predictions
    Your "80% confident" beliefs should come true about 80% of the time — check that they do.
    Bayesian Thinking: How to Update Beliefs Rationally
  6. Calibrated Questions, Made Practical
    Calibrated questions are open "How" and "What" questions that hand the other party a problem to solve, letting you steer a negotiation or difficult conversation without commands or ultimatums. The technique comes from Chris Voss’s FBI hostage-negotiation work; its mechanism is grounded in autonomy psychology, though the specific scripts are practitioner craft rather than a lab-validated protocol.
  7. Maintain a scored prediction log
    Record predictions with explicit probabilities and score them when they resolve.
    Calibration Training
  8. Practice probability calibration
    Regularly make probabilistic predictions and track your accuracy across many of them.
    Hindsight Bias: Why Everything Seems Obvious in Retrospect
  9. Calibration practice
    Predict your performance before each retrieval test, then compare prediction to outcome.
    Self-Regulated Learning: Taking Control of How You Learn
  10. Track your estimates and calibrate
    Compare your Fermi estimates to actual figures when you can, and use the gap to improve future estimates.
    Fermi Estimation

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