Coaching practices for How to Enumerate Scenarios

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

  • I keep playing out this decision in my head as if there’s just one way it goes
  • A scenario laid out as a vivid story grips me, but the moment I’d try to say it plainly
  • I’ve lived inside this scenario so long that every piece feels obvious to me
  • I’m bracing for and planning around the absolute worst version of how this goes, and it hasn’t even crossed my mind that there’s a whole range of ordinary, fine outcomes that are far likelier than the one I keep rehearsing.
  • My plan only works if a whole chain of things all go right

Practices that may help

  1. Enumerate scenarios and their probabilities before deciding
    Write down each meaningful outcome, assign a probability, and compute the weighted total.
    Expected Value Thinking: Deciding Under Uncertainty
  2. Strip the narrative and restate as a bare frequency claim
    Translate the vivid scenario into a dry statistical question to see if it still feels probable.
    The Conjunction Fallacy — When "More Details" Feels More Likely
  3. Consult an outside observer to counteract narrative pull
    Describe the scenario to someone who doesn’t share your narrative context and listen to their probability estimate.
    The Conjunction Fallacy — When "More Details" Feels More Likely
  4. Map best case, worst case, and most likely case
    Write out all three scenarios to reanchor your thinking in the probable, not just the feared.
    Decatastrophizing, Made Practical
  5. Audit plans for scenario inflation
    Before committing to a plan that depends on multiple things going right, count the dependencies.
    The Conjunction Fallacy — When "More Details" Feels More Likely
  6. Think in scenarios and stories, not task lists
    Describe your ideal outcome for a period as a short narrative before breaking it into actions.
    Getting Results the Agile Way (AGS), Made Practical
  7. Stress test plans against outcomes beyond the historical range
    Ask how your plan holds up if the worst outcome is twice as bad as any historically observed case.
    The Ludic Fallacy: When You Mistake Real Life for a Game
  8. Run a mental simulation before committing to a course of action
    Before acting on a recognized situation, mentally run through how your intended response plays out.
    Recognition-Primed Decision Making
  9. Run a pre-mortem from the outside-view perspective
    Imagine the project has failed — then ask which base-rate failure type caused it.
    The Outside View
  10. Accumulate varied situational episodes to move from novice to competent
    Build a library of real cases — not just more rules — to develop situational recognition.
    The Dreyfus Model: Five Stages from Novice to Expert

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