/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.