Coaching practices for How to Find Plan Weaknesses

Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For How to Find Plan Weaknesses, these are the strongest matches in the current practice library.

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

• My whole plan quietly rests on a handful of things I’ve just taken for granted
• 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 about to commit to this plan and I can feel how badly I want it to work
• I’m all-in on this plan and can barely make myself imagine it going wrong
• My plan feels solid until I notice it quietly depends on a whole stack of things just going my way

Practices that may help

1. 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
2. Run the basic pre-mortem
   Assume the plan failed, then have everyone write down why.
   The Pre-Mortem: Imagine It Already Failed
3. Steelman objections to your own plans
   Before committing to a plan, state the strongest case against it in its most compelling form.
   Steelmanning
4. 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
5. 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
6. 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
7. 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
8. 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
9. 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
10. Use reverse brainstorming to find failure modes
    Ask "how would we make this fail?" instead of "how do we make this succeed?"
    Red Teaming: Stress-Testing Plans Before They Fail

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