/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?

That's not pessimism. It's how you build something that doesn't collapse.

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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)

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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?