Difficult Conversation Preparation Script
Prepare for a hard conversation — with a partner, manager, parent, or friend — so you can be honest and kind without escalating or shutting…
Get clear on any important decision using a structured thinking framework — including a pre-mortem, a reversibility check, and a hidden option scan.
You are a sharp, clear-headed thinking partner. Help me make a better decision using structured reasoning. The decision I'm facing: [describe the decision clearly] Options I'm considering: [list 2–4 options, or say "I haven't named them yet"] What I'm optimizing for: [e.g. freedom, income, stability, growth, happiness, values alignment] My current gut instinct: [what my gut says — and why I'm not just following it] What I'm afraid of: [the fears underneath this decision] Timeline: [when does this need to be decided] Who else is affected: [people whose lives this decision touches] Walk me through: 1. Decision Clarification — restate the real decision I'm facing. Sometimes we solve the wrong problem. 2. Option Mapping — each option with honest pros/cons and what it specifically optimizes for 3. Values Check — which option best aligns with what I said I'm optimizing for — and where there's tension 4. Fear Audit — which of my stated fears are realistic and which are imagined. Name each one. 5. Pre-Mortem — it's 6 months from now and the decision I made was wrong. What happened? Walk through this for each option. This surfaces failure modes that optimism hides. 6. 10/10/10 Test — how will I feel about this in 10 minutes / 10 months / 10 years 7. Reversibility Check — how hard is this to undo if it's wrong? Does that change the calculus? 8. The Hidden Option — is there an option I haven't considered, a hybrid, or a reframe that changes the decision entirely 9. Your Recommendation — what you'd advise, with reasoning. Don't hedge. Say what you'd actually recommend. Be honest. Don't tell me what I want to hear.
Career decisions, life choices, business decisions, personal crossroads.
A structured decision analysis covering clarification, option mapping, values check, fear audit, pre-mortem for each option, 10/10/10 test, reversibility check, hidden option scan, and a direct recommendation.
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Claude Sonnet 4
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