--- 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*) 2. **The "Secret" Check:** Is the proposal built on a unique truth, or just conventional wisdom? (Source: Thiel, *Zero to One*) ### Step 2: Perform the Inversion Audit List all the specific ways the proposal could lead to a catastrophic failure. (Source: Munger, Ch. 2) 1. **The Pre-Mortem:** Imagine it is 12 months from now and the project has failed. What specifically happened? (Source: Duke, *How to Decide*) 2. **Reverse the Goal:** What actions would we take if we *wanted* this project to fail? Are we currently doing any of those things? ### Step 3: Detect Systemic Fragility Evaluate how the proposal handles volatility and "Black Swan" events. (Source: Taleb, Ch. 1) 1. **Non-Linear Downside:** Is there a "cliff" where a small change in inputs leads to a massive failure? 2. **Capped Upside:** Is the reward for success small relative to the cost of failure? ### Step 4: Steel-Man the Opposition Construct the absolute strongest argument *against* the core thesis. 1. **Competitor View:** How would a smart, resourced competitor invalidate this plan? 2. **The Skeptic's Evidence:** What data exists that contradicts the author's primary claims? ### Step 5: The "So What?" and Sensitivity Check Challenge the conclusion's impact and robustness. 1. **The Needle Check:** Even if the author is 100% right, does it move the needle for the business? 2. **The 10% Swing:** If key metrics (conversion, cost, timing) swing +/- 10%, does the plan still hold together? (Source: Gil, *High Growth Handbook*) ## Frameworks & Models ### The Checklist for Misjudgment (Source: Munger, *Poor Charlie's Almanack*) Audit the proposal for the 25 standard psychological biases, including: 1. **Reward-Superresponse:** Are incentives driving bad logic? 2. **Incentive-Caused Bias:** Does the author benefit from the proposal being accepted, regardless of its truth? 3. **Consistency and Commitment:** Is the author stuck in a previous decision? ### Via Negativa (Source: Taleb, *Antifragile*) 1. **Subtract to Strengthen:** What should we *stop* doing or *remove* from this proposal to make it more robust? 2. **Remove the "I-Knew-It-All-Along" bias:** Document current predictions to prevent future "hindsight bias." ## Cross-Skill Invocations - **REQUIRED SUB-SKILL:** `mental-model-library` — Use cross-domain models (Inversion, Second-order thinking) for analysis. - **RECOMMENDED SUB-SKILL:** `assumption-audit` — To validate the evidence for key claims. - **RECOMMENDED SUB-SKILL:** `decision-frameworks` — To structure the final choice after the stress test. ## Common Mistakes 1. **Straw-Manning:** Attacking a weak version of the opposing argument to make the original look better. (Source: Graham, "Think") 2. **Resulting:** Judging a proposal based on a lucky success in a different context. (Source: Duke, Ch. 1) 3. **The Lollapalooza Trap:** Ignoring how multiple small risks can combine into a massive failure. (Source: Munger, Ch. 3) ## Diagnostic Checklist - [ ] Have we identified the "Linchpin" assumption that must be true for success? - [ ] Have we performed a "Pre-Mortem" identifying 3+ specific failure paths? - [ ] Have we "Steel-Manned" the strongest possible counter-argument? - [ ] Is the proposal "Antifragile" (does it benefit or stay robust under volatility)? - [ ] Have we assigned confidence percentages to all "certain" assertions? ## Sources - Duke, *Thinking in Bets*, Ch. 1, 2, 3 — Anti-Resulting, Certainty Bias, Cuckolding Luck. - Munger, *Poor Charlie's Almanack*, Ch. 2, 4 — Inversion, Psychology of Human Misjudgment. - Taleb, *Antifragile*, Ch. 1, 22, 24 — Fragility, Via Negativa, Skin in the Game. - Farnam Street, "Inversion" & "Probabilistic Thinking" — Applied mental models. - Paul Graham, "How to Think for Yourself" — Independent thinking vs. consensus.