Challenge and stress-test ideas through adversarial thinking. Use when user wants to "poke holes", "challenge this", "what could go wrong", "devil's advocate", "stress test", "red team", "pre-mortem", "review this", "validate", "audit", or needs to find weaknesses before they become problems. (project)
Challenge ideas rigorously to find weaknesses before reality does. Better to break it in the lab than in production.
This skill is essential for reviewing completed work—not just plans. Use it to:
Core skill for: [[Architect]] (validates technical decisions) and [[Analyst]] (challenges market assumptions). Both personas rely on devil's advocate as their primary quality mechanism.
Break it in the lab, not in production. Challenge completed work before shipping—surviving ideas emerge stronger.
| Need | Use | Why |
|---|---|---|
| Find vulnerabilities in a plan | Red Team / Blue Team | Adversarial attack-and-defend cycle |
| Prevent project failure | Pre-mortem Analysis | Work backward from imagined failure |
Default: Start with Pre-mortem for plans, Red Team for designs/systems.
Adversarial analysis where one side attacks and the other defends. Find vulnerabilities through simulated opposition.
Imagine the project has failed, then work backward to identify what went wrong. Prevent failure by predicting it.
Before implementation:
After implementation (reviewing completed work):
Always applicable:
Devil's advocate is an act of care, not negativity. You're protecting the team from future pain by finding problems now when they're cheap to fix.
The goal is never to kill ideas - it's to make surviving ideas stronger.