Harshly critique strategic documents (validation reports, competitive analyses, business plans) to identify blind spots, challenge assumptions, expose weaknesses, and generate Conductor-aligned action plans.
NewMaintained
Automatic
◆Product Management pack
Last verified 8/23/2026
What it changes
2 of 22 test cases passed with the skill.
Pass-rate lift
—
Tokens
+110%
Agent turns
0%
Response time
+13%
Model gemini-3.6-flashMeasured 8/23/2026v12 of 22 cases passed with skill · 3 comparable
Tokens, turns and time describe resource use, not a dollar price.
Lift withheld: 3 comparable cases; this report requires 8.
See it in action
A test case the skill fixed. Same model, same prompt, with and without the skill.
Prompt
We completed a red-team review of B2B SaaS architecture proposal in enterprise_plan.md. Generate the action plan section for the critique report markdown file. Include all required fields for each action item to ensure it is fully actionable.
What was checked, without and with the skill
Checked
Without skill
With skill
Each action item in the action plan includes Priority, Action, Rationale, Conductor Artifact, Success Criteria, and Timeline fields.
Missed
Passed
Action items map technical changes to tech-stack.md or workflow.md.
Missed
Passed
case-06 · gemini-3.6-flash · 8/23/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md243 lines3 files
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:
Assume failure first - Start from "this will fail" and work backward
Challenge everything - No assumption is sacred
Seek disconfirming evidence - Look for what contradicts the plan
Think like competitors - How would they exploit your weaknesses?
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.