devils-advocate

Challenge core assumptions using pre-mortem, assumption reversal, and red team critiques.

Updated Apr 7, 2026
One-click install
npx skills add https://github.com/haabe/tic-tac-toe --skill devils-advocate-haabe
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: devils-advocate
Source: https://github.com/haabe/tic-tac-toe/tree/main/.claude/skills/devils-advocate
Command: npx skills add https://github.com/haabe/tic-tac-toe --skill devils-advocate-haabe

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Systematically challenge current assumptions before major decisions, countering confirmation bias, groupthink, and overconfidence.

Core Features & Use Cases

  • Technique 1: Pre-Mortem — Imagine it's 6 months from now and this decision FAILED spectacularly; identify what went wrong, the weakest link in assumptions, ignored signals, and affected parties.
  • Technique 2: Assumption Reversal — For each key assumption, state it explicitly, ask what if the opposite is true, what evidence would support the opposite, and whether any evidence has been dismissed.
  • Technique 3: Red Team — Attack your own position by considering competitor, skeptical user, security auditor, and accessibility advocate perspectives.
  • When to Use — Before major design transitions, architecture decisions, or committing to a specific solution; use when certainty feels high.

Quick Start

Act as a devil's advocate and stress-test this decision by walking through Pre-Mortem, Assumption Reversal, and Red Team critiques.

Frequently Asked Questions about devils-advocate

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I challenge assumptions and prevent bias during architecture decisions?

To challenge assumptions during architecture decisions, apply structured critique techniques like pre-mortem, assumption reversal, and red team analysis. This surfaces hidden biases and documents decision logs by guiding evidence-based reasoning and explicit assumption articulation from multiple vantage points.

What is a pre-mortem analysis and when should I use it for product strategy?

A pre-mortem analysis is a decision-making technique where you imagine a major product strategy decision failed spectacularly six months later, then identify what went wrong. Use it before major design transitions or architecture reviews when team certainty feels high to counter overconfidence.

How do I run a red team critique on my own design or architecture proposal?

To run a red team critique, attack your own position by evaluating the proposal from competitor, skeptical user, security auditor, and accessibility advocate perspectives. This structured stress-testing identifies ignored signals and affected parties before committing to a specific solution.

What is assumption reversal and how does it counter confirmation bias?

Assumption reversal is a decision-making method where you state a key assumption explicitly, ask what if the opposite is true, and identify what evidence would support that opposite. It counters confirmation bias by forcing you to examine whether any evidence has been unfairly dismissed.

When should I not use devil's advocate techniques for decision-making?

You should avoid using devil's advocate techniques for routine, low-stakes operational choices where the overhead of structured critique outweighs the risk of bias. Reserve pre-mortem, red team, and assumption reversal methods for major design transitions, architecture decisions, and high-certainty strategic pivots.