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Strategy/devils-advocate

Devil's Advocate

Challenge your PRDs and specs to find blind spots, hidden assumptions, and potential failure scenarios.

Time Saved

1-2 hours → 10 min

Compared to doing it manually

Slash Command

/devils-advocate

Type this in Claude to run the skill

The Problem

You're about to present a proposal that feels solid, but you have no one to pressure-test it. You need someone to poke holes in your thinking before skeptical stakeholders do it for you in the meeting.

What You Get

  • ✓Critical questions challenging your key assumptions
  • ✓Potential failure scenarios with likelihood and impact assessment
  • ✓Blind spots you haven't considered
  • ✓Unintended consequences and second-order effects
  • ✓The hard questions skeptical stakeholders will ask
  • ✓Recommended actions to address top risks

Want this automated?

This skill is part of a workflow that automate multiple steps together:

Multi-Perspective Review

Agent Workflow

7 stakeholder perspectives. 15 minutes. Done.

7 skills automated
2 hrs → 15 min

How to use this skill

  1. 1Download the skill file using the button on this page
  2. 2Add the file to your .claude/skills/ folder in your project
  3. 3Type /devils-advocate in Claude to run the skill

Best For

Stress-testing high-stakes proposals before stakeholder reviewFinding assumptions you're taking for grantedPreparing for tough questions from executives or skepticsGetting a reality check when something feels too easy

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Frequently Asked Questions

A devil's advocate review challenges your proposal by asking "what could go wrong?" It identifies hidden assumptions, potential failure scenarios, and unintended consequences you may have missed.

Use it when a proposal feels too easy or when you have no one to pressure-test your thinking. It's especially valuable before presenting to skeptical stakeholders or making high-risk decisions.

Related but different. Risk analysis identifies known risks and mitigation strategies. Devil's advocate challenges your assumptions and finds blind spots you didn't know existed. It's more exploratory.

Not all challenges will be real risks — some are edge cases. The value is in forcing you to think through "what if?" scenarios you hadn't considered. Prioritize challenges that expose assumptions you took for granted.

View Workflow →