Coaching practices for How to Identify Plan Failures

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

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

• 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 about to commit real time and money to this plan, and it looks solid
• My whole plan is a chain where every link has to hold
• 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. Run the basic pre-mortem
   Assume the plan failed, then have everyone write down why.
   The Pre-Mortem: Imagine It Already Failed
2. 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
3. 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
4. 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
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. Run a pre-mortem to interrupt forward narrative construction
   Before committing to a plan, imagine it failed completely — then generate the most plausible story of why.
   The Narrative Fallacy: Why We Can’t Stop Making Stories
7. Review and update action plans at a fixed weekly cadence
   An action plan that is not reviewed weekly becomes stale — regular review keeps the plan matched to current reality.
   Action Planning
8. 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
9. 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
10. 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

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