Coaching practices for How to Run a Pre Mortem

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

  • I want to look back from the very end of my life and ask honestly what I actually did with my time
  • When I ask myself "what could go wrong with this plan," I either draw a blank or come up with one vague worry
  • I keep putting off the things I say matter most as if I have unlimited time, and I’m losing days to small grievances and "somedays"
  • I’m about to commit real time and money to this plan, and it looks solid
  • I’m all-in on this plan and can barely make myself imagine it going wrong

Practices that may help

  1. The Pre-Mortem: Imagine It Already Failed
    A pre-mortem, developed by psychologist Gary Klein, has a team imagine that a plan has already failed and then work backward to explain why — before any work begins. The technique exploits "prospective hindsight": research found that imagining an outcome as a certainty makes people generate more, and more specific, reasons for it, surfacing risks that ordinary risk assessment misses.
  2. Write a brief final accounting
    Write as if you’re reporting on your life: what did you do with your time?
    Memento Mori: Using Mortality Awareness to Focus What Matters
  3. Run the basic pre-mortem
    Assume the plan failed, then have everyone write down why.
    The Pre-Mortem: Imagine It Already Failed
  4. Memento mori as the ultimate premeditation
    Premeditate the final loss — your own death — as a clarifier of what actually matters now.
    Premeditatio Malorum, in Depth
  5. Run a pre-mortem before committing to a plan
    Imagine the plan has already failed and ask what went wrong.
    Confirmation Bias: Seeing What You Expect to See
  6. 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
  7. Pair the pre-mortem with a clear success vision
    Balance failure analysis with an equally concrete picture of what success requires.
    The Pre-Mortem: Imagine It Already Failed
  8. Combine the pre-mortem with red team pressure
    Run a pre-mortem and then ask the red team to find the failure mode the team missed.
    Red Teaming: Stress-Testing Plans Before They Fail
  9. Memento Mori: Using Mortality Awareness to Focus What Matters
    Memento mori — "remember you will die" — is the Stoic practice of keeping mortality in view as a clarifier: trivial concerns shrink and important ones become urgent when measured against a real deadline. Used well, it sharpens values and action; used badly, it slides into death anxiety. The psychological evidence is genuinely mixed — mortality awareness can produce either defensiveness or value-driven clarity depending on the person and how the awareness is held.
  10. Run a premortem before committing
    Imagine the project has already failed and work backwards to find why.
    The Planning Fallacy — Why Your Estimates Are Always Wrong

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