Prompts & heuristics

These are the lines I come back to when things get noisy. Short. Memorable. Usable mid-meeting.

Discovery

1. If you cannot explain the problem in one sentence, you do not understand it yet.
2. If your “user” is a department, you’re missing the real person doing the work.
3. The best discovery question is: “What do you do today when this fails?”
4. If you don’t know what success looks like, you’re just collecting opinions.
5. A feature request is rarely the real request; ask what outcome they’re buying.
6. If you can’t find three concrete examples, you probably have a hypothesis, not a problem.
7. Don’t ask users what they want; ask what they’re trying to avoid.

Prioritization

8. The loudest stakeholder is not the same as the highest cost of delay.
9. If everything is priority one, nothing is.
10. If you can’t name the tradeoff, you didn’t prioritize.
11. The feature engineering estimates as easy is rarely the one users care about most.
12. A roadmap is a list of sacrifices; write down what you’re not doing.
13. If the metric won’t change in a month, pick an input metric you can influence.
14. “Strategic” without a measurable outcome is just a strong feeling.

Delivery

15. If you didn’t write a non-goal, you guaranteed scope creep.
16. A requirement written as UI is a guess; a requirement written as an outcome is a constraint.
17. When timelines slip, ask what changed: scope, capacity, dependencies, or risk.
18. If you can’t rollback safely, you’re not ready to launch.
19. The fastest way to lose trust is to hide a risk until it becomes a fire.
20. Don’t confuse motion with progress; progress has a measurable change.
21. Every meeting should end with a decision, an owner, or a cancelled calendar invite.