/challenge-that

description: Force critical evaluation of proposals from 5 adversarial perspectives

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.