Pick the three whose answers change the shape of the work. Not the three that are easiest to answer.
Always
- What number does this need to move, and what is it today?
- Who has final say, and who else has to be brought along?
- What is the hard date, and what is it hard because of?
Net-new product
- Who has this problem badly enough to change their behaviour?
- What are they doing instead today — including the spreadsheet?
- What is the smallest version that would still be worth shipping?
- Which part are you most afraid is wrong?
Redesign of something live
- What does the analytics say people actually do, versus what you designed for?
- What breaks most often in support tickets?
- What must not change, and who would object if it did?
- Has this been redesigned before? What happened?
Design system engagement
- Who are the consumers, and can they be made to adopt it?
- Is there a coded library today, and does it match the design source?
- Who owns it after we leave, and do they have the time?
- What is the release and deprecation process — or is there none?
Regulated / trust-critical
- Which decisions require a compliance or legal reviewer, and how long do they take?
- What happens to a user when the system is wrong? Who absorbs it?
- What must be auditable, logged, or reversible?
AI features
- What does the product do when the model is unsure, wrong, or unavailable?
- Can the user correct it, and does the correction persist?
- What is the human-in-the-loop step, and who is that human?
Ambiguity probes — when stakeholders disagree
- If we could only fix one thing this quarter, which?
- What would make you say, in six months, that this was a waste?
- Who is the user you'd most hate to lose?