Strategy Critique

Strategy Critique

Red-team any strategy document. Find what's missing before reality does.

Workflow

1. Read the strategy doc — Accept a vault path, file path, URL, or inline text. Identify:

   • Stated goals and success metrics
   • Key assumptions (explicit and implicit)
   • Proposed approach and timeline
   • Resource requirements
   • Dependencies and constraints

2. Identify assumptions — List every assumption the strategy relies on, including:

   • Explicit assumptions — stated in the doc
   • Implicit assumptions — unstated but required for the strategy to work
   • Hidden assumptions — things the author likely takes for granted

3. Stress-test each assumption — For each assumption:

   • How confident should we be? (HIGH / MEDIUM / LOW)
   • What evidence supports it?
   • What would falsify it?
   • What happens to the strategy if it's wrong?

4. Find gaps — Look for:

   • Missing stakeholders — who is affected but not considered?
   • Unaddressed risks — what failure modes aren't covered?
   • Resource gaps — what's needed but not budgeted?
   • Timeline gaps — what dependencies could cause delays?
   • Competitive gaps — how might competitors respond?
   • Second-order effects — what downstream consequences are ignored?

5. Score overall robustness — Rate the strategy:

   • Assumption quality: How solid are the foundations? (1-10)
   • Completeness: How many important areas are covered? (1-10)
   • Adaptability: How well does it handle surprises? (1-10)
   • Overall robustness: Weighted average (1-10)

6. Write constructive recommendations — For each major gap or weak assumption, suggest a concrete fix.

Output Format

## Strategy Critique: [Document Title]

### Summary
[2-3 sentence assessment — what's strong, what's concerning]

### Robustness Score: [X]/10
- Assumption quality: [X]/10
- Completeness: [X]/10
- Adaptability: [X]/10

### Assumptions Audit

| # | Assumption | Type | Confidence | If Wrong |
|---|-----------|------|-----------|----------|
| 1 | [assumption] | Explicit | HIGH | [consequence] |
| 2 | [assumption] | Implicit | LOW | [consequence] |

### Gaps Found

#### 1. [Gap Title]
**What's missing**: ...
**Why it matters**: ...
**Suggested fix**: ...

### Strongest Elements
- [What's genuinely well-done — be specific]

### Recommendations
1. [Highest-priority fix]
2. [Second-priority fix]
3. [Third-priority fix]

Behavior

• Be adversarial but constructive — the goal is to strengthen the strategy, not tear it down
• Acknowledge what's genuinely strong before critiquing
• Distinguish between fatal flaws and nice-to-haves
• If the strategy is actually solid, say so — don't manufacture criticisms
• Save output to vault if requested: vault/decisions/critique-[topic]-[YYYY-MM-DD].md