Devil's Advocate Pattern

A prompt pattern that asks Claude to argue against a document from multiple skeptical perspectives. Used to stress-test documents before real audiences see them. Surfaces weaknesses, gaps, and unconvincing sections.

Syntax

claude-documentation

Here is my [document type]:
[paste document]

Play devil's advocate. If you were:
1. An investor who decided NOT to invest — top 3 reasons
2. A competitor who heard this plan — what would you exploit
3. A skeptical board member — what questions would you ask

Be specific. Reference the actual document content.

Example

claude-documentation

// Applied to a pitch deck
Here is my Series A pitch deck content:
[paste pitch deck content]

Play devil's advocate:
1. As a Series A VC who passed — list your top 3 specific objections
2. As a competitor who saw this — where is the moat weakest
3. As a board member — what data is missing to support these projections

Do not give generic feedback. Reference specific slides and claims.