Coaching practices for How to Develop Judgment

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

  • I’ve made hundreds of these judgment calls over the years and yet my gut feels no sharper than when I started
  • There’s someone whose judgment I deeply admire, and I keep asking them "what would you do?" and just copying their answer
  • I just made a hard call under real uncertainty and I keep wondering whether someone with genuinely good judgment would have handled it differently
  • I beat myself up over a call that went badly even though it was reasonable with what I knew, and I pat myself on the back for a reckless one that happened to work
  • Left to my own judgment I either think I’m better than I am or get scared off the very things that would help most

Practices that may help

  1. Build wisdom through case-based reflection
    After a consequential decision, reconstruct what you perceived, what you valued, and what you’d change.
    Phronesis: Aristotle’s Practical Wisdom
  2. Learn from a phronimos (a practically wise person)
    Identify someone whose judgment you respect, and study how they read situations — not just what they decide.
    Phronesis: Aristotle’s Practical Wisdom
  3. Developing phronesis: practical wisdom through reflection
    After a significant decision, reflect on what a practically wise person would have done — and update your judgment for next time.
    Aristotelian Eudaimonia: Flourishing Through Virtue
  4. Score decision quality separately from outcome quality
    Judge the process you used — not whether it worked — when you review a past decision.
    Decision Journaling: Learning to Decide Better Over Time
  5. Judgments of Learning: Why You Misjudge What You’ve Learned
    Judgments of learning (JOLs) are in-the-moment predictions about how well information will be remembered later. Thomas Nelson’s research showed JOLs are often inaccurate — biased upward by current processing fluency — causing learners to declare items "learned" prematurely and under-study material they will later forget. Delayed JOLs and retrieval-based checks produce more accurate predictions and better study-time allocation.
  6. Use a challenge-calibration partner or coach
    Have a more skilled observer set the challenge level — your own assessment is biased.
    Growth-Edge Training: Practicing at the Edge of Your Ability
  7. Replace judgment with non-judgmental awareness
    Observe what is actually happening with curious interest rather than approval or disapproval.
    The Inner Game: Quieting Self 1
  8. Decision Journaling: Learning to Decide Better Over Time
    A decision journal is a written record of significant decisions — what you decided, why, what you expected to happen, and what actually happened. It counteracts hindsight bias and outcome bias by preserving your actual reasoning before the outcome arrives, and it creates the only feedback loop that produces real calibration: comparing your predictions to results across many decisions over time.
  9. Restudy decision protocol
    Use a defined decision rule — not a feeling — to determine which items get additional study.
    Judgments of Learning: Why You Misjudge What You’ve Learned
  10. Track your calibration across many predictions
    Score your confidence levels against outcomes over dozens of predictions to find your systematic biases.
    Decision Journaling: Learning to Decide Better Over Time

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