Sometimes you need AI to challenge your thinking aggressively. Devil's Advocate prompting pushes back on your ideas to strengthen them.
The Constructive Challenger Approach
```text "Play devil's advocate on my plan to [plan]. Ask tough questions that: - Expose weaknesses in my logic - Challenge optimistic assumptions - Identify overlooked risks - Question resource estimates - Probe competitive responses But do so constructively, helping me build a stronger plan." ```text
Devil's Advocate Patterns
Pattern 1: The Stress Test ```text "I believe [strategy] will work because [reasons]. Challenge each reason with: - What evidence contradicts this? - When has this failed before? - What are we conveniently ignoring? - How might competitors exploit this?" ```text Pattern 2: The Pre-Mortem ```text "Assume my [project/decision] fails spectacularly in one year. Through Socratic questioning, help me discover: - What went wrong? - What warning signs did I miss? - What assumptions proved false? - How could I have prevented this?" ```text Pattern 3: The Opposition Research ```text "If you were my biggest competitor/critic, what questions would you ask to undermine my [plan/argument]? Help me prepare strong responses." ```text