SKILL FILE

Devil's Advocate with AI

Stress-test your product ideas, PRDs, and roadmaps by simulating a skeptical investor — surface blind spots and the tough questions you'll get in review.

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What this skill file teaches Claude

Drop one markdown file into your repo. Claude Code learns how to run this entire workflow.

1

Assumption excavation

Surfaces the assumptions you're making implicitly — and stress-tests each one.

2

Failure mode mapping

What could go wrong, ranked by likelihood × impact. Often the unsexy answers.

3

Stakeholder objections

Anticipates the specific objections from CFO / CTO / Sales / Legal so you can have the answer ready.

4

Sanity-check questions

A list of "before you ship this, can you answer these?" questions to take to your team.

5

Honest reality check

Tells you when your idea is too easy ("if this is so obvious, why hasn't someone done it?") and when to slow down.

What you can build with this

Pre-review pressure test

Run your PRD or brief through it before the formal review meeting. Fix the holes before someone else finds them.

Reality-check a "too easy" idea

Something feels suspiciously simple? Devil's Advocate digs for what you're missing.

Prep for tough stakeholders

You know the CFO will ask about ROI; the CTO about scalability. Get the questions surfaced and answered in advance.

Get the full skill file

Everything above is 80% of the skill file. Download the complete version with full implementation details, agent prompts, and ready-to-run scripts.

Common questions

No — it specifically targets weak points and assumptions, not the whole idea. The output is actionable (what to fix) not blanket dismissal.
Yes — works on marketing campaigns, hiring decisions, strategy memos, any document where you want pushback before committing.
Your team has biases (loyalty, pattern-matching, conflict-avoidance). The skill is structurally adversarial — it's designed to disagree. Use it BEFORE asking your team so the team conversation focuses on the real risks.
A PRD, a brief, a strategy doc, a roadmap, a pitch deck — any structured argument works. The longer/clearer the input, the sharper the pushback.
No — it makes formal reviews MORE useful by clearing the obvious objections first. Then the meeting focuses on the harder questions that need human judgment.

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