The 4-Question
Pressure Test

On a scale of 1-10, how confident are you in the answer you just gave me? Be honest. Calibration matters more than sounding sure. Specifically tell me: 1. THE SCORE A single number, 1-10. 2. WHY THAT SCORE AND NOT HIGHER What’s making you less than fully sure? (Thin training data, ambiguous question, fast-moving field, conflicting sources, my missing context, etc.) 3. WHY THAT SCORE AND NOT LOWER What’s genuinely solid in your answer? Where are you on firm ground? 4. WHICH PARTS ARE WHICH Walk through your answer and tag each major claim: - HIGH CONFIDENCE: I’d defend this - MEDIUM CONFIDENCE: directionally right, details may be off - LOW CONFIDENCE: educated guess, verify before acting 5. WHAT WOULD PUSH THE SCORE UP The 2-3 specific things you’d need to know or check to move from a 6 to a 9. (More context from me? A specific source? A different framing of the question?) RULE: Don't just lower the score to look humble. If a claim depends on facts that change fast (prices, laws, product features, anything after your training data), say so and mark it LOW until it's checked.

Where could the answer you just gave me fall apart? What’s the version of this answer that would be wrong, and for whom? Specifically: 1. THE TOP 3 WAYS THIS COULD BE WRONG The most plausible scenarios where your answer doesn’t hold. Rank them by likelihood. For each, tell me what would have to be true for the failure to happen. 2. THE ASSUMPTIONS YOU MADE List every assumption baked into your first answer. Things you assumed about my situation, my context, my industry, my level of expertise, my goals. Flag the ones I haven’t confirmed. 3. THE EDGE CASES YOU SKIPPED The unusual-but-real situations where your answer breaks. Be specific. Not “in some cases this might not apply,” but “if you’re in [X situation], the answer flips because [Y].” 4. THE STEELMAN OPPOSITE Argue the opposite of what you said. Make the strongest possible case for the OTHER answer. What would the smart person who disagrees with you say? 5. THE TELL What signal in MY situation would tell me your answer doesn’t apply? What should I look for in my own context to know I’m the exception?

Now take the perspective of a top expert in this field, someone who’s been doing this for 20+ years and has the scars to prove it. Critique your previous answer like they would. Specifically: 1. NAME THE EXPERT First, define who this expert IS. (Not a real person, a role: “a senior IP attorney with 20 years in tech transactions,” “a CFO who’s taken 3 companies through Series B,” “a family medicine doctor with a focus on autoimmune.”) Be specific about their lens. 2. WHAT YOU GOT RIGHT What in your first answer would the expert nod at? Don’t pad. Only the genuinely solid parts. 3. WHAT YOU OVERSIMPLIFIED What did you flatten that this expert would say has more nuance? Where would they push back on a generalization? 4. WHAT AN AMATEUR GETS WRONG HERE THAT THE EXPERT NEVER WOULD The 1-3 mistakes a smart-but-non-expert (which your first answer often is) typically makes in this domain, and which of them showed up in your answer. 5. THE EXPERT’S REWRITE Rewrite your original answer the way the expert would deliver it. Same goal, different depth. Use the actual frameworks, vocabulary, and judgment calls a real expert would. 6. THE EXPERT’S FOLLOW-UP QUESTION The single question this expert would ask me before fully committing to an answer. (This is usually the most useful sentence of the whole pressure test.)

How would I verify your answer on my own? Tell me exactly what to check, where to check it, and how long it’ll take. Specifically: 1. THE 3-5 SPECIFIC THINGS TO CHECK Not generic “do research.” The actual sources, calculators, documents, or people. For each item: - WHAT to verify (the specific claim from your answer) - WHERE to verify it (the actual source: government site, specific tool, named expert, calculator URL, person to call) - WHY this is the highest-signal verification (vs. easier-but-weaker checks) 2. THE 30-MINUTE VERIFICATION PLAN If I have 30 minutes, the exact sequence: do A first, then B, then C. Use web search to find the real sources and give me working links. Never make up a URL; if you can't find one, name the source and tell me what to search for. 3. THE 5-MINUTE GUT-CHECK VERSION If I’m time-strapped: the single fastest check that’d catch the most likely error. The 80/20 of verification. 4. THE ONE MOST IMPORTANT THING If I only verify ONE thing from your answer before acting, what is it? The single highest-stakes claim: the one where being wrong matters most. 5. WHEN TO BRING IN A HUMAN The threshold at which I should stop trusting AI verification and bring in a real expert (lawyer, doctor, CPA, engineer, etc.). What signal would tell me “this is past the AI’s pay grade”? 6. WHAT WOULD CHANGE YOUR ANSWER If I come back and tell you what I found in verification, what specific finding that would make you revise your original answer materially? Tell me so I know what to bring back to you.