Challenge That
Force critical evaluation by analyzing from multiple adversarial perspectives.
When Invoked
- Identify what was just accepted/proposed in this conversation
- State it clearly: "Challenging: [the proposal/decision]"
- Analyze from each of the five perspectives below
- Synthesize into actionable concerns
- 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.