challenge

Topics in the source

• /executive-mentor:challenge — Pre-Mortem Plan Analysis
• The Core Idea
• When to Run a Challenge
• The Challenge Framework
• Step 1: Extract Core Assumptions
• Step 2: Rate Each Assumption
• Step 3: Map Vulnerabilities
• Step 4: Find the Dependency Chain

Command: /executive-mentor:challenge Systematically finds weaknesses in any plan before reality does. Not to kill the plan — to make it survive contact with reality. -- 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. -- 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) -- 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 re

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