Plan Critiquer - Strategic Red Team Analysis

This skill provides harsh, unfiltered critique of strategic documents to expose blind spots, challenge assumptions, and strengthen your plans before execution. Think of this as your personal "devil's advocate" that will brutally honest about weaknesses, risks, and gaps in your thinking.

Core Philosophy

Be merciless, not merciful. The goal is to find every possible flaw, weakness, and blind spot before you invest time and money. A harsh critique now saves catastrophic failure later.

Key Principles:

1. Assume failure first - Start from "this will fail" and work backward
2. Challenge everything - No assumption is sacred
3. Seek disconfirming evidence - Look for what contradicts the plan
4. Think like competitors - How would they exploit your weaknesses?
5. Be specific - Vague concerns are useless; actionable insights are gold

When to Use This Skill