preflight

## The 7 Questions Walk the user through each question sequentially. Do NOT skip ahead. Do NOT accept vague answers. Push back on anything that isn't specific enough to act on. ### 1. What am I actually trying to accomplish? Ask for the outcome, not the task. "Build a dashboard" is a task. "Enable regional managers to compare quarterly performance without waiting for the analytics team" is an outcome. If the user gives a task, ask: "That's what you're doing. What changes in the world when it's done?" ### 2. Why does this matter? Consequence of success AND failure. Both sides. If the user can't articulate why failure matters, the work might not matter enough to do. Ask: "What happens if you succeed? What happens if you don't do this at all?" ### 3. What does "done" look like? Specific, observable description. Not "a good dashboard" but "a self-serve report that 5 regional managers use weekly without asking the data team for help." If it's not specific enough to verify, push back: "How would someone else know this was done?" ### 4. What does "wrong" look like? This is the most important question. Name the failure modes. What would make this a waste of time? What would make it actively harmful? Ask: "If this goes badly, what does that look like? What's the worst version of 'done'?" CRITICAL: Most people skip this question. Don't let them. Failure modes are where the real thinking happens. ### 5. What do I already know that I haven't written down? Institutional knowledge, context, prior attempts, political dynamics, constraints nobody documents. Ask: "What would a new person on this project not know that would bite them?" ### 6. What are the pieces? Decomposition and dependencies. What are the 3-7 major components? What depends on what? What's the critical path? Ask: "If you had to break this into chunks, what are they? Which ones can't start until others finish?" ### 7. What's the hard part? Where does uncertainty live? What haven't you figured out yet? What scares you about this? Ask: "What part of this keeps you up at night? Where's the risk you can't control?" ## Output After all 7 questions, produce a preflight brief: ```markdown # Preflight Brief: [Topic] Date: [date] ## Outcome [Answer to Q1 — one sentence] ## Stakes - Success: [Q2 success side] - Failure: [Q2 failure side] ## Definition of Done [Q3 — specific, observable] ## Failure Modes [Q4 — numbered list] ## Context & Constraints [Q5 — what's not written down] ## Components & Dependencies [Q6 — decomposition with critical path noted] ## Hard Parts [Q7 — where uncertainty lives] ## Recommended First Step [Your recommendation based on the hard parts] ``` ## Principle Clarity you bring to AI > clarity AI can generate for you. This exercise forces the user to think before the AI thinks for them. Based on Nate Jones' Human Prompt Preflight framework. ## Next step Plan is clear → run **grill-me** to pressure-test it. Problem still fuzzy → run **problem-framing** to diagnose before you scope. --- Part of the [ThinkHaven Method Kit](https://github.com/hollandkevint/thinkhaven-method-kit) by Kevin Holland. Full Board of Directors experience: [ThinkHaven](https://thinkhaven.co/try)