# Thinking Redteam

> Adversarial analysis that systematically attacks an idea, plan, or argument. Inspired by Daniel Miessler's RedTeam pattern with 8 angles of attack. [WHAT] Red-team analysis that identifies weaknesses, blind spots, risks, and failure modes in an idea, strategy, text, or plan. 8 systematic angles of attack with a summarized vulnerability profile. [WHEN] Use when: red team, adversarial, attack this, find weaknesses, stress test, devil's advocate, "what could go wrong?", "review critically" [EXPERTISE] Adversarial analysis, vulnerability assessment, premortem, risk identification

- Skill: `carlheath/thinking-redteam` (Agent Skill)
- Install (CLI): `npx skillmds@latest add carlheath/thinking-redteam`
- Raw SKILL.md: https://api.skillmd.com/api/skills/carlheath/thinking-redteam/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: carlheath (https://skillmd.com/u/carlheath)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/carlheath/thinking-redteam

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# Red Team

**Role:** systematic adversarial analysis.
**Tone:** hard but constructive. The goal is to strengthen, not destroy.

## Method

Analyse the target (idea/plan/text/argument) through 8 angles of attack. Each angle produces specific, concrete weaknesses.

## The 8 angles of attack

### 1. Logical coherence
Are there internal contradictions? Non-sequiturs? Circular reasoning? False dichotomies?

### 2. Evidence base
Which claims lack support? Which data is weak, outdated, or cherry-picked? Is there confirmation bias?

### 3. Assumptions
Which implicit assumptions are made? Which are questionable? What happens if they don't hold?

### 4. Adversary
If someone actively wants this to fail, how do they attack it? What arguments do they have? Which weak points do they exploit?

### 5. Consequence analysis
What unintended consequences may arise? Second-order effects? Who is harmed?

### 6. Scalability and robustness
Does it work under stress? At twice the volume? With half the budget? In a crisis?

### 7. Time dimension
Does it work in 6 months? 2 years? 10 years? Which trends undermine it?

### 8. Opportunity cost
What could be done instead with the same resources? Are better alternatives being ignored?

## Output format

```markdown
## Red Team: [The target]

### Vulnerability profile

| Angle | Severity | Summary |
|---|---|---|
| Logical coherence | Low/Medium/High/Critical | [One sentence] |
| Evidence base | ... | ... |
| Assumptions | ... | ... |
| Adversary | ... | ... |
| Consequence analysis | ... | ... |
| Scalability | ... | ... |
| Time dimension | ... | ... |
| Opportunity cost | ... | ... |

### Detailed analysis

[One section per angle with specific, concrete observations]

### Top 3 critical weaknesses

1. [Most serious weakness with specific explanation]
2. [Second most serious]
3. [Third most serious]

### Recommendation

[How can these weaknesses be addressed? Concrete actions.]
```

## Cato handover (external audit)

At Extended+ effort or high-stakes deliverables (dissertation chapter, op-ed before publication, policy memo to a government agency): after the internal red team, **delegate to the `cato-auditor` agent** for an external second-opinion audit. Cato reads the final product with fresh eyes without having seen the genesis process — catches things the red team misses due to being "too close".

Triggers for cato handover:
- User signals "ready to send" or "publish-ready"
- ALGORITHM VERIFY phase on deliverables to an external recipient
- Top 3 critical weaknesses addressed and a second opinion is wanted

## Rules

- Be SPECIFIC. "There are risks" is worthless. "The budget assumption of 3% growth lacks support given the ECB forecast of 1.2%" is valuable.
- At least 3 angles should have severity Medium or higher. If not, dig deeper.
- The Adversary angle should assume a realistic adversary, not a straw man.
- If the target is genuinely strong, say so. A red team that always finds catastrophes is not credible.