devils-advocate

name	devils-advocate
type	domain
family	executive
rigor	standard
description	Use when a proposal has unanimous support or relies on a single high-impact assumption—constructs the strongest possible counter-argument (Steel Man) and runs a Pre-Mortem.
keywords	stress-testing, adversarial, challenge, risk-identification, critique, validation
compatibility	Claude Code and compatible agent products
requires	[]
enhances	["strategy-clarity","assumption-audit","decision-frameworks"]
sources_pdf	["Thinking in Bets (Duke)","Poor Charlie's Almanack (Munger)","Antifragile (Taleb)","Seeking Wisdom (Bevelin)","How to Decide (Duke)"]
sources_web	["Paul Graham: How to Think for Yourself","Farnam Street: Inversion","Farnam Street: Probabilistic Thinking"]

Overview

The Devil's Advocate is an intellectually rigorous stress-test designed to dismantle arguments, expose blind spots, and "steel man" opposing viewpoints. This skill replaces vague skepticism with structured adversarial analysis—using inversion, fragility detection, and probabilistic auditing to ensure a proposal can survive an unforgiving market.

Guiding Principles

Principle 1: Invert, Always Invert (Source: Munger, Poor Charlie's Almanack)

To solve a problem or test a plan, think about what would cause the opposite of the desired result. Listing all the ways a plan could fail is more effective than listing why it will succeed. (Source: Farnam Street, "Inversion")

Principle 2: Anti-Resulting (Source: Duke, Thinking in Bets)

Never judge a decision solely by its outcome. A "good" result can come from a "bad" process due to luck. The Devil's Advocate must audit the decision process, not just the projected result.

Principle 3: Fragility Detection (Source: Taleb, Antifragile)

Any proposal that relies on things "staying the same" or has non-linear downside and capped upside is fragile. Strategy should aim for "Optionality"—the ability to benefit from volatility.

Principle 4: Steel-Manning (Source: Paul Graham, "How to Think for Yourself")

Do not create a "straw man" of the opposition. Instead, build the absolute strongest version of the counter-argument. If the original proposal can't survive the "Steel Man," it is fundamentally weak.

Principle 5: The Certainty Audit (Source: Duke, How to Decide)

We tend to believe we "know" things that are only probable. Force a percentage confidence score on every key assertion. If an assertion is "certain," it is likely a blind spot.

When to Use This Skill

• When a strategic proposal has unanimous "groupthink" support.
• When an analysis relies on a single high-impact assumption (a "linchpin").
• Before presenting a high-stakes recommendation to a board or executive leadership.
• When evaluating a complex project with significant "downside" risk.

When NOT to Use This Skill

• During early-stage creative brainstorming where critique might stifle ideation.
• For minor, low-stakes tactical decisions where speed is more important than rigor.

Core Process

Step 1: Identify the Linchpin Assumption

Determine the single weakest foundational assumption in the overall thesis.

1. The "What Must Be True" Test: What is the one thing that, if proven false, collapses the entire argument? (Source: Lafley, Playing to Win)