Coaching practices for How to Evaluate a Plan

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

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

• One future excites me but I don’t believe I could pull it off, another I could do but it’d cost me who I am
• I made a plan a while back, my life has shifted since, and I keep failing the same plan over and over without ever sitting down to actually update it to fit how things are now.
• My plan feels solid until I notice it quietly depends on a whole stack of things just going my way
• I’m about to lock in a plan that feels airtight from the inside
• In my head my plan feels totally clear, but every time I go to actually do it I realize I never decided the details and it falls apart

Practices that may help

1. Rate each plan on confidence, interest, and coherence
   Score each plan on whether you find it engaging, whether you could execute it, and whether it fits who you are.
   Odyssey Plans: Designing Three Alternative Futures
2. 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
3. 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
4. Invoke the outside view before committing to any significant plan
   Before finalizing a plan or forecast, ask "How did similar things go?" as the first checkpoint.
   The Outside View
5. Test your action plan for specificity before relying on it
   Before counting on a plan, check that a stranger could execute it from your written description — if not, it is not specific enough.
   Action Planning
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. 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
8. Steelman objections to your own plans
   Before committing to a plan, state the strongest case against it in its most compelling form.
   Steelmanning
9. Run the basic pre-mortem
   Assume the plan failed, then have everyone write down why.
   The Pre-Mortem: Imagine It Already Failed
10. 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

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