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challenge
Use before committing serious resources to a plan, or when feedback has been suspiciously positive. Runs a pre-mortem: assume it failed in 12 months and work back to the assumptions, dependencies and execution risks.
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# /executive-mentor:challenge — Pre-Mortem Plan Analysis
**Command:** `/executive-mentor:challenge <plan>`
Systematically finds weaknesses in any plan before reality does. Not to kill the plan — to make it survive contact with reality.
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## The Core Idea
Most plans fail for predictable reasons. Not bad luck — bad assumptions. Overestimated demand. Underestimated complexity. Dependencies nobody questioned. Timing that made sense in a spreadsheet but not in the real world.
The pre-mortem technique: **imagine it's 12 months from now and this plan failed spectacularly. Now work backwards. Why?**
