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:

# 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 by Kevin Holland. Full Board of Directors experience: ThinkHaven