challenge-that

# Challenge That Force critical evaluation by analyzing from multiple adversarial perspectives. ## When Invoked 1. Identify what was just accepted/proposed in this conversation 2. State it clearly: "**Challenging:** [the proposal/decision]" 3. Analyze from each of the five perspectives below 4. Synthesize into actionable concerns 5. Ask: "Which concerns should we address before proceeding?" ## The Five Hats | Hat | Focus | Key Questions | |-----|-------|---------------| | 🔴 **Skeptic** | Evidence & proof | "What evidence supports this? Has this been validated? Are we guessing?" | | 🟡 **Pragmatist** | Cost/benefit | "Is this the simplest fix? What's the maintenance burden? Is it worth it?" | | 🟢 **Edge Case Hunter** | Failure modes | "What breaks this? What's the worst case? What did we miss?" | | 🔵 **Structural Critic** | Architecture | "Is this the right location? Does it fit the existing design? Will it cause problems elsewhere?" | | 🟣 **Root Cause Analyst** | Problem diagnosis | "Is the problem correctly identified? Are we treating symptoms? What's the actual cause?" | ## Output Format ``` ## Challenging: [proposal/decision being challenged] ### 🔴 Skeptic [Challenge from evidence/proof perspective] ### 🟡 Pragmatist [Challenge from cost/benefit perspective] ### 🟢 Edge Case Hunter [Challenge from failure modes perspective] ### 🔵 Structural Critic [Challenge from architecture perspective] ### 🟣 Root Cause Analyst [Challenge from problem diagnosis perspective] --- **Key Concerns:** 1. [Most significant concern] 2. [Second concern] 3. [Third concern] Which of these should we address before proceeding? ``` ## Rules 🚨 **Be genuinely adversarial.** Don't softball the challenges. If a perspective finds nothing wrong, say so—but look hard first. 🚨 **Challenge the proposal, not the person.** Focus on the idea's weaknesses, not who suggested it. 🚨 **Provide actionable output.** Each challenge should point to something that could be investigated or changed.