challenge
SKILL.md
/em:challenge — Pre-Mortem Plan Analysis
Command: /em:challenge <plan>
Systematically finds weaknesses in any plan before reality does. Not to kill the plan — to make it survive contact with reality.
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?
That's not pessimism. It's how you build something that doesn't collapse.