# Critique Framework - Multi-Pass Strategic Analysis

> This framework provides a systematic, harsh approach to critiquing strategic documents.

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- Author: tools-only (https://skillmd.com/u/tools-only)
- Updated: 2026-09-29
- Page: https://skillmd.com/skills/tools-only/critique-framework-multi-pass-strategic-analysis

---

# Critique Framework - Multi-Pass Strategic Analysis

This framework provides a **systematic, harsh approach** to critiquing strategic documents. The goal is to identify blind spots, uncover hidden assumptions, challenge optimistic thinking, and expose weaknesses **before** they become failures.

## Critique Mindset

**Adopt the "Skeptical Investor" Persona:**
- You've seen 1,000 pitches; 990 failed
- You're looking for reasons to say NO
- You've been burned by optimistic projections before
- You demand evidence, not enthusiasm
- You think in probabilities, not possibilities

**Key Questions to Keep in Mind:**
- "Why will this fail?" (not "will it fail?")
- "What are they not telling me?"
- "What do they not know that they don't know?"
- "How would I exploit this if I were a competitor?"

---

## Pass 1: The "Gut Check" (Intuitive Analysis)

**Purpose:** Capture immediate reactions before deep analysis biases your intuition.

### Clarity and Cohesion
- **Does the narrative make sense?** Can you explain the core idea in one sentence?
- **Do sections connect logically?** Or does it feel like disconnected research pasted together?
- **Is there a consistent vision?** Or does the strategy shift between sections?
- **Red flags:** Jargon overload, contradictory statements, vague language, buzzword bingo

### Completeness
- **What's missing?** What questions immediately come to mind that aren't answered?
- **Are there obvious holes?** Unaddressed competitors? No pricing strategy? No go-to-market plan?
- **Does it feel rushed?** Shallow analysis? Missing data? Handwaving over hard problems?
- **Red flags:** "We'll figure that out later," "This is beyond scope," "Assumed to be true"

### Confidence Level
- **Does this inspire confidence?** Would you invest your own money?
- **Realistic or optimistic?** Are projections grounded or aspirational?
- **Do they know what they don't know?** Or is there false confidence?
- **Red flags:** "Easy to implement," "No real competition," "Guaranteed success," "Conservative estimates" that aren't

### Gut Check Output
Write 3-5 sentences capturing your immediate reaction:
- Overall impression (excited, concerned, skeptical?)
- Biggest strength
- Biggest weakness
- One question that must be answered

---

## Pass 2: Assumption Hunting (Logical Analysis)

**Purpose:** Identify and challenge the foundational beliefs the plan relies on.

### Step 1: Extract Assumptions

Read through the document and identify statements that are:
- Presented as fact but lack evidence
- Projections about future behavior (users will..., competitors won't...)
- Dependencies (if X then Y)
- Beliefs about market, technology, or customers

**Common assumption categories:**
- **Market assumptions:** Size, growth rate, willingness to pay
- **Customer assumptions:** Pain points, behavior, preferences
- **Competitive assumptions:** What competitors will/won't do
- **Technology assumptions:** What's possible, reliable, scalable
- **Execution assumptions:** Team capability, timeline, resources
- **Economic assumptions:** Costs, pricing, unit economics

### Step 2: Prioritize Assumptions

For each assumption, assess:
- **Impact if wrong:** (High/Medium/Low) - What happens if this is false?
- **Evidence strength:** (Strong/Weak/None) - How well is this supported?
- **Testability:** (Easy/Hard/Impossible) - Can we validate this quickly?

**Focus on:** High impact + Weak evidence = Critical risk

### Step 3: Challenge Each Critical Assumption

For the top 5-10 assumptions, ask:

**Evidence Challenge:**
- "What is the evidence for this assumption?"
- "Is the evidence strong, or just a single data point?"
- "Could the evidence be interpreted differently?"
- "Is the source credible and recent?"

**Falsification Challenge:**
- "What if this assumption is completely wrong?"
- "What would need to happen for this to be invalidated?"
- "What would we observe if this were false?"
- "Have we looked for disconfirming evidence?"

**Testing Challenge:**
- "How can we test this assumption quickly and cheaply?"
- "What experiment would validate or invalidate this?"
- "What's the minimum viable test?"
- "What would success/failure look like?"

### Step 4: Identify Hidden Assumptions

Look for **unstated beliefs** that underpin the strategy:
- "We assume we can hire the right talent"
- "We assume our tech stack can scale"
- "We assume customers will switch from existing solutions"
- "We assume we can execute faster than competitors"
- "We assume market conditions won't change"

### Assumption Hunting Output

Create a table:

| Assumption | Impact if Wrong | Evidence Strength | Test Method | Priority |
|------------|-----------------|-------------------|-------------|----------|
| [Statement] | High/Med/Low | Strong/Weak/None | [How to test] | HIGH/MED/LOW |

---

## Pass 3: Pre-Mortem / Failure Analysis (Adversarial Thinking)

**Purpose:** Imagine the project has failed and work backward to identify causes.

### Step 1: Set the Failure Scenario

**Imagine:** It's 6 months from now. The project has failed spectacularly.
- Money is gone
- Team has disbanded or pivoted
- Customers didn't materialize or churned
- Investors/stakeholders are angry
- Competitors are thriving

**Write the headline:** "[Your Project] Shuts Down After 6 Months - Here's What Went Wrong"

### Step 2: Brainstorm Failure Reasons

Generate as many failure causes as possible. Think in categories:

**Internal Failures (Things We Control):**
- **Execution:** Couldn't build it, took too long, quality issues
- **Team:** Key person left, skill gaps, conflicts
- **Product:** Wrong features, bad UX, technical debt
- **Strategy:** Wrong market, wrong pricing, wrong positioning
- **Resources:** Ran out of money, couldn't hire, couldn't scale

**External Failures (Things We Don't Control):**
- **Competition:** Competitor copied our features, new entrant crushed us
- **Market:** Demand didn't materialize, economic downturn
- **Technology:** Key API shut down, costs exploded, quality degraded
- **Regulation:** Content policies changed, compliance issues
- **Timing:** Too early (market not ready) or too late (market saturated)

### Step 3: Categorize and Prioritize Failure Modes

For each failure reason:
- **Likelihood:** (High/Medium/Low) - How probable is this?
- **Impact:** (Catastrophic/Severe/Moderate) - How bad would this be?
- **Preventability:** (Preventable/Mitigatable/Uncontrollable) - Can we do anything?

**Focus on:** High likelihood + Catastrophic impact + Preventable = Must address

### Step 4: Develop Mitigation Strategies

For top 5-10 failure modes, create specific mitigation plans:

**For preventable risks:**
- What can we do NOW to prevent this?
- What early warning signs should we watch for?
- What's our contingency plan if this starts happening?

**For mitigatable risks:**
- How can we reduce the likelihood?
- How can we reduce the impact?
- What's our backup plan?

**For uncontrollable risks:**
- Can we build resilience against this?
- Can we diversify to reduce dependency?
- Should we reconsider the strategy if this risk is too high?

### Pre-Mortem Output

Create a risk register:

| Failure Mode | Likelihood | Impact | Preventability | Mitigation Strategy | Owner |
|--------------|------------|--------|----------------|---------------------|-------|
| [Cause] | H/M/L | Catastrophic/Severe/Moderate | P/M/U | [Specific actions] | [Who] |

---

## Pass 4: Competitive & Market Blind Spots (External Reality Check)

**Purpose:** Challenge the plan from the perspective of competitors, customers, and market forces.

### Competitive Analysis

**Unaddressed Competitors:**
- **Direct:** Who else solves this exact problem?
- **Indirect:** Who solves the underlying need differently?
- **Emerging:** Who's building something that could disrupt this space?
- **Substitutes:** What do people use today instead?

**For each competitor, ask:**
- "Why would they let us succeed?"
- "What would they do if we started winning?"
- "Do they have resources/brand to crush us?"
- "How quickly could they copy our differentiation?"

**Competitive Response Scenarios:**
- **Top competitor adds our key feature:** What happens to our moat?
- **Big tech company enters the market:** Can we compete with their distribution?
- **Open-source alternative emerges:** How do we survive?

### Customer Perspective

**Problem-Solution Fit:**
- "Would I actually pay for this?" (Be honest)
- "What friction would stop me from buying?"
- "What objections would I have?"
- "What alternatives would I consider first?"

**Customer Objections (Anticipate):**
- "The output looks generic" → How do we overcome this?
- "I can use a free tool" → Why pay us?
- "I need a human expert" → When does automation not work?
- "I don't trust AI with this" → How do we build trust?

**Jobs-to-be-Done Analysis:**
- What job is the customer hiring this product to do?
- What are they using today to do this job?
- Why would they fire their current solution?
- What would make them fire our solution?

### Market Dynamics

**Macro Trends (PESTLE Analysis):**
- **Political:** Regulation, policy changes
- **Economic:** Recession impact, budget constraints
- **Social:** Perception changes, trust in AI, behavior shifts
- **Technological:** AI advancement (helps or hurts?), new tools
- **Legal:** Liability, IP issues, compliance
- **Environmental:** (Usually less relevant for software)

**Market Maturity:**
- Is this market growing or saturating?
- Are we early, on-time, or late?
- What stage of adoption curve? (Innovators, early adopters, early majority...)

### Differentiation Stress Test

**For each claimed competitive advantage, ask:**

**Uniqueness:**
- "Is this truly unique, or just rare?"
- "How many competitors could claim something similar?"
- "Is this a feature or a fundamental advantage?"

**Defensibility:**
- "How hard is this to copy?" (Weeks? Months? Years?)
- "What prevents competitors from doing this?"
- "Is this protected by patents, data, network effects, or brand?"

**Sustainability:**
- "Will this advantage last 6 months? 1 year? 3 years?"
- "What could erode this advantage?"
- "Are we building a moat or just a speed bump?"

**Value:**
- "Do customers actually care about this?"
- "Would they pay more for this?"
- "Is this a nice-to-have or a must-have?"

### Market Blind Spots Output

Document:
1. **Unaddressed competitors** (3-5 that weren't mentioned)
2. **Customer objections** (5-10 reasons customers might not buy)
3. **Market risks** (3-5 macro trends that could derail this)
4. **Differentiation weaknesses** (Which advantages are fragile?)

---

## Pass 5: Synthesis & Prioritization (Strategic Integration)

**Purpose:** Consolidate findings into actionable insights.

### Step 1: Consolidate Findings

Review all outputs from Passes 1-4 and identify:
- **Patterns:** Do multiple passes reveal the same concern?
- **Themes:** Are there categories of risk (e.g., all tech-related, all market-related)?
- **Contradictions:** Does the plan claim X but evidence suggests Y?

### Step 2: Categorize Critiques

Organize findings into:

**Strategic Concerns** (Vision, positioning, market opportunity)
**Assumption Gaps** (Unverified beliefs, weak evidence)
**Competitive/Market Oversights** (Unaddressed threats, customer objections)
**Execution Risks** (Resources, timeline, capability)

### Step 3: Assess Overall Viability

Based on all findings, make a judgment:

**GO** - Strong plan with manageable risks
- Critical assumptions are validated or testable
- Competitive advantages are defensible
- Risks are identified with mitigation plans
- Execution is realistic

**GO WITH CAUTION** - Promising but significant risks
- Some critical assumptions unvalidated
- Competitive moat is thin but improvable
- Risks are addressable but require work
- Execution is challenging but feasible

**STOP** - Fundamental flaws that can't be easily fixed
- Critical assumptions are likely false
- No defensible competitive advantage
- Risks are catastrophic and unmitigatable
- Execution is unrealistic

### Step 4: Prioritize Actions

For each finding, assign:
- **Priority:** HIGH (must address before proceeding) / MEDIUM (address soon) / LOW (monitor)
- **Effort:** LOW (days) / MEDIUM (weeks) / HIGH (months)
- **Impact:** HIGH (changes strategy) / MEDIUM (refines approach) / LOW (minor adjustment)

**Prioritization Matrix:**
- HIGH priority + LOW effort = Do immediately
- HIGH priority + HIGH effort = Plan carefully, allocate resources
- LOW priority + LOW effort = Quick wins, do if time permits
- LOW priority + HIGH effort = Defer or skip

### Step 5: Generate Specific Actions

For each HIGH and MEDIUM priority finding, create a specific action:

**Bad (vague):** "Research competitors more"
**Good (specific):** "Conduct 10 user interviews asking: 'Why did you choose [competitor] over alternatives?' Document objections and switching costs."

**Bad (vague):** "Validate pricing"
**Good (specific):** "Run landing page A/B test with 3 pricing tiers. Drive 1,000 visitors via ads. Success = >5% email signup rate."

### Step 6: Map to Conductor Artifacts

For each action, identify which Conductor files need updating:

**`product.md`** - Vision, features, target users, success metrics
**`product-guidelines.md`** - Messaging, positioning, brand voice
**`tech-stack.md`** - Technology choices, dependencies, scalability
**`workflow.md`** - Development practices, quality gates, validation processes
**`tracks.md`** - New tracks for validation, research, prototypes
**New track** - For substantial work requiring spec + plan

### Synthesis Output

Create:
1. **Executive Summary** (2-4 paragraphs with overall assessment)
2. **Critical Risks Table** (Top 5-10 with priority, impact, mitigation)
3. **Action Plan** (Prioritized list with Conductor mapping)
4. **Recommended Next Steps** (Top 3 immediate actions)

---

## Advanced Techniques

### Inversion Thinking
Instead of "How do we succeed?" ask "How do we guarantee failure?"
- What would make this fail fastest?
- What's the worst decision we could make?
- How would we sabotage ourselves?

Then invert: Avoid those things.

### Second-Order Consequences
Don't just identify risks - think through cascading effects:
- "If API costs spike, then margins compress, then we raise prices, then customers churn, then we lose revenue, then we can't afford API costs..."

### Competitive War Gaming
Role-play as competitors:
- "I'm the top competitor. The new entrant is gaining traction. What do I do?"
- "I'm the platform giant. Should I crush them or acquire them?"
- "I'm a well-funded startup. Do I care about this market?"

### Customer Empathy Mapping
For target persona:
- **Think:** What are they worried about?
- **Feel:** What emotions drive their decisions?
- **Say:** What objections would they voice?
- **Do:** What actions would they take (or not take)?

---

## Quality Checklist

Before finalizing critique, verify:

- **Specific** - Every concern has concrete examples
- **Evidence-based** - Claims are supported by data or logic
- **Actionable** - Every finding leads to a clear next step
- **Prioritized** - Not everything is equally important
- **Balanced** - Acknowledges strengths while exposing weaknesses
- **Harsh but constructive** - Brutal honesty with path forward
- **Conductor-aligned** - Actions map to specific artifacts

**Avoid:**
- Vague concerns ("This might not work")
- Unsupported opinions ("I don't think customers will pay")
- Unconstructive criticism ("This is bad")
- Analysis paralysis (100 risks, no prioritization)
- False positivity (ignoring real problems to be nice)