Coaching practices for How to Find Risks in a Plan

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

  • My plan feels solid until I notice it quietly depends on a whole stack of things just going my way
  • When I ask myself "what could go wrong with this plan," I either draw a blank or come up with one vague worry
  • I’m all-in on this plan and can barely make myself imagine it going wrong
  • I’m excited about this plan and so committed to it that I can’t honestly see what might sink it
  • We ran a real critique of the plan, found genuine holes, wrote them all down in a nice risk list

Practices that may help

  1. Name the assumptions that must hold for the plan to work
    Every plan rests on assumptions — list them and ask how likely each one is.
    Margin of Safety
  2. Run the basic pre-mortem
    Assume the plan failed, then have everyone write down why.
    The Pre-Mortem: Imagine It Already Failed
  3. 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
  4. Run a premortem before committing
    Imagine the decision has already failed — then ask why.
    Thinking in Bets
  5. Require the plan to change, not just the risk register
    A red team exercise that doesn’t change the plan has accomplished nothing.
    Red Teaming: Stress-Testing Plans Before They Fail
  6. Map and stress-test your key assumptions
    Before executing, list the assumptions the plan depends on — then ask which ones would kill it if wrong.
    Red Teaming: Stress-Testing Plans Before They Fail
  7. Design decisions so they work even if some things go wrong
    Ask: does this plan require everything to go right? If so, redesign it.
    Margin of Safety
  8. Stress-test your withdrawal plan against multiple scenarios
    Run your plan against the worst historical periods — not just the average — before retiring.
    The 4 Percent Rule, Made Practical
  9. 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
  10. The premortem (imagine the project already failed)
    Before starting, assume the plan has already failed and ask why — then fix it now.
    Premeditatio Malorum, in Depth

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