Customer Discovery Questions
The questions that surface the real problem, the constraints, and the definition of success — before you write a line of code.
The problem (not the feature)
- Walk me through it
- “Show me how you do this today, step by step.” Watch, don’t ask them to summarize.
- Cost of the status quo
- “What does this cost you now — time, money, errors, missed revenue?”
- Last time it hurt
- “Tell me about the last time this went wrong.” Specifics beat generalities.
- Who feels the pain
- “Who does this today, and how many of them?”
- Why now
- “Why is this worth solving this quarter and not last year?”
Success & scope
- Definition of done
- “If this works perfectly, what’s different on Monday morning?”
- The one metric
- “What number would move that tells us it worked?”
- Good enough
- “What accuracy / latency / coverage is good enough to be useful?”
- The demo bar
- “What would you need to see to believe this is real?”
Constraints (find the landmines)
- Where can it run
- “Cloud, your VPC, on-prem, air-gapped? Who approves that?”
- Data rules
- “Can data leave your network? Any PII / regulated data (HIPAA, PCI)?”
- Systems to touch
- “What systems hold the data — and who owns access to them?”
- Security review
- “What does it take to get a new tool approved here?”
People (map the room)
- Champion
- “Who wants this to succeed and will fight for it internally?”
- Blocker
- “Whose approval could stop this — security, legal, a skeptical lead?”
- Decision maker
- “Who signs off / holds the budget?”
- The user
- “Who actually uses it daily — and do they want it?”