/plan-critiquer

name: plan-critiquer
description: Harshly critique strategic documents (validation reports, competitive analyses, business plans) to identify blind spots, challenge assumptions, expose weaknesses, and generate Conductor-aligned action plans. Use when you need brutal honesty, "red team" analysis, or want to stress-test your thinking before execution. Applies multiple analytical frameworks (pre-mortem, assumption hunting, competitive gaps, market dynamics) and synthesizes findings into executive summaries with specific, actionable recommendations mapped to Conductor context artifacts.

Plan Critiquer - Strategic Red Team Analysis

This skill provides **harsh, unfiltered critique** of strategic documents to expose blind spots, challenge assumptions, and strengthen your plans before execution. Think of this as your personal "devil's advocate" that will **brutally honest** about weaknesses, risks, and gaps in your thinking.

Core Philosophy

**Be merciless, not merciful.** The goal is to find every possible flaw, weakness, and blind spot **before** you invest time and money. A harsh critique now saves catastrophic failure later.

**Key Principles:** 1. **Assume failure first** - Start from "this will fail" and work backward 2. **Challenge everything** - No assumption is sacred 3. **Seek disconfirming evidence** - Look for what contradicts the plan 4. **Think like competitors** - How would they exploit your weaknesses? 5. **Be specific** - Vague concerns are useless; actionable insights are gold

When to Use This Skill

• After completing market validation or competitive analysis
• Before committing significant resources to a plan
• When you need to stress-test strategic assumptions
• Before presenting to investors, stakeholders, or team
• When you feel "too confident" about a plan (overconfidence bias check)
• After receiving positive feedback (to balance optimism with realism)

Workflow

Step 1: Identify and read_file Input Documents

The user will provide one or more strategic documents to critique. Common types:

• Validation reports
• Competitive analyses
• Business plans
• Market research summaries
• Product roadmaps
• Go-to-market strategies

read_file all provided documents completely to understand the full context.

Step 2: Load Critique Framework

read_file `references/critique_framework.md` - this contains the multi-pass analytical framework with specific questions and techniques for identifying blind spots.

Step 3: Apply Critique Framework (Multi-Pass Analysis)

Systematically apply **all passes** from the framework:

**Pass 1: Gut Check**

• Does the narrative make sense?
• Are there obvious holes or inconsistencies?
• Does it inspire confidence or raise red flags?

**Pass 2: Assumption Hunting**

• Identify the 5-10 most critical assumptions
• Challenge each: "What if this is wrong?"
• Assess evidence strength for each assumption
• Identify assumptions that are unverified or weakly supported

**Pass 3: Pre-Mortem (Imagine Failure)**

• Assume the project failed spectacularly in 6 months
• Brainstorm all possible failure reasons (internal + external)
• Categorize and prioritize failure modes
• Identify which failures are preventable vs. uncontrollable

**Pass 4: Competitive & Market Blind Spots**

• Unaddressed competitors (direct, indirect, emerging)
• Customer perspective gaps (are we solving their problem?)
• Market dynamics not considered (regulatory, technological, social trends)
• Differentiation weaknesses (how easy to copy? how defensible?)

**Pass 5: Synthesis**

• Consolidate findings across all passes
• Identify patterns and themes
• Prioritize by impact and likelihood
• Generate specific, actionable recommendations

Step 4: Generate Critique Report

Create a comprehensive critique report with the following structure:

Executive Summary (2-4 paragraphs)

• **Overall Assessment:** GO / GO WITH CAUTION / STOP (with brief rationale)
• **Critical Risks:** Top 3 deal-breaker risks that could kill the project
• **Key Blind Spots:** Top 3 areas where thinking is incomplete or flawed
• **Recommended Actions:** High-level next steps to address findings

Detailed Critique & Blind Spots

Organize findings by category:

**Strategic Concerns**

• Vision/positioning weaknesses
• Market opportunity gaps
• Competitive positioning flaws
• Business model vulnerabilities

**Assumption Gaps**

• Unverified assumptions with high impact
• Weak evidence for critical beliefs
• Optimistic projections without validation
• Hidden dependencies

**Competitive/Market Oversights**

• Unaddressed competitors or substitutes
• Market dynamics not considered
• Customer objections not addressed
• Differentiation weaknesses

**Execution Risks**

• Resource constraints
• Timeline unrealism
• Capability gaps
• Dependency risks

For each finding:

• **State the concern clearly**
• **Explain the impact** (what happens if this is wrong?)
• **Assess likelihood** (how probable is this risk?)
• **Provide evidence** (what makes you think this?)

Step 5: Create Conductor-Aligned Action Plan

Generate a **prioritized, specific action plan** that maps recommendations to Conductor context artifacts.

For each action item: 1. **Priority:** HIGH / MEDIUM / LOW 2. **Action:** Specific, measurable task (not vague like "research more") 3. **Rationale:** Why this matters (link to critique finding) 4. **Conductor Artifact:** Which file(s) to update (`product.md`, `tech-stack.md`, `workflow.md`, etc.) 5. **Success Criteria:** How to know when this is complete 6. **Timeline:** Suggested timeframe (days/weeks)

**Conductor Artifact Mapping Guidelines:**

• **`product.md`** - Update for: vision changes, feature prioritization, target user refinements, success metrics
• **`product-guidelines.md`** - Update for: messaging, positioning, brand voice, terminology
• **`tech-stack.md`** - Update for: technology choices, dependencies, infrastructure, scalability concerns
• **`workflow.md`** - Update