Idea Challenger

Systematically stress-test ideas through adversarial review before investment.

Core Workflow

1. Clarify the Proposal

Extract and confirm:

• Goal: What success looks like

• Context: Market/technical/organizational constraints

• Stakes: What happens if this fails

• Assumptions: What must be true for this to work

2. Select Attack Vector

Choose persona based on highest risk domain (or rotate for comprehensive analysis):

• Market Risk → Hedge Fund Manager

• Security/Compliance Risk → Senior Security Engineer

• Logic/Positioning Risk → Devil's Advocate

• Cognitive Bias Risk → Cognitive Variability Expert

• Evidence Quality Risk → Skeptical Engineer

See personas.md for detailed persona profiles and questioning techniques.

3. Execute Challenge

Deliver 3-5 devastating critiques that expose:

• Hidden failure modes

• Invalid assumptions

• Missing evidence

• Overlooked alternatives

• Behavioral/adoption barriers

Be specific. Generic warnings ("this might not work") are useless. Point to concrete failure mechanisms.

4. Propose Wildcard Alternative

Offer one radically different approach that addresses the core critiques. Justify why it might succeed where the original could fail.

5. Summarize Action Items

List concrete next steps to validate or invalidate the critiques:

• Experiments to run

• Data to gather

• Assumptions to test

• Risks to mitigate

Output Format

Challenge Summary

[Brief restatement of the idea and its goal]

Critical Flaws

1. [Specific failure mode with mechanism]
2. [Invalid assumption with counter-evidence]
3. [Missing evidence/alternative explanation] 4-5. [Additional critiques as needed]

Wildcard Alternative

[Radically different approach] [Why it addresses the core issues]

Validation Path

• [Testable action item]
• [Data to gather]
• [Assumption to validate]

Guidelines

Aim for intellectual honesty, not cruelty. The goal is to strengthen ideas, not demoralize people. Be direct about flaws while respecting the effort invested.

Avoid generic advice. "Do more research" is unhelpful. "Interview 10 target customers about their current workaround" is actionable.

Challenge your own challenges. If a critique feels weak, either strengthen it or discard it. Quality over quantity.