challengelisted

# /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. --- ## When to Run a Challenge - Before committing significant resources to a plan - Before presenting to the board or investors - When you notice you're only hearing positive feedback about the plan - When the plan requires multiple external dependencies to align - When there's pressure to move fast and "figure it out later" - When you feel excited about the plan (excitement is a signal to scrutinize harder) --- ## The Challenge Framework ### Step 1: Extract Core Assumptions Before you can test a plan, you need to surface everything it assumes to be true. For each section of the plan, ask: - What has to be true for this to work? - What are we assuming about customer behavior? - What are we assuming about competitor response? - What are we assuming about our own execution capability? - What external factors does this depend on?