Customer interview questions for startups: 30 prompts that work

last updated: Sep 8, 2025
Interview notes template for customer interview questions for startups

TL;DR

Customer interview questions for startups that any founder can use. Recruit five to fifteen right-fit users, ask the 30 prompts below, then synthesize exact phrases into your deck, landing page, and value proposition. Includes recruitment email, consent snippet, note template, and a one-page board.

How to:
  • Recruit the right five. Use a tight screener and a simple outreach email.
  • Run 30 prompts. Stay on the last painful moment. Do not pitch.
  • Synthesize in one hour. Tag pains, workarounds, triggers, WTP, and next actions.

Glossary

  • JTBD (jobs to be done): why users “hire” a product.
  • WTP (willingness to pay): price user says feels fair and why.
  • Screener: short filter to admit only target users.
  • Incentive: cash, voucher, or access you offer for time.
  • Consent: clear note about recording and use of quotes.
  • Design partner: early user who co-builds in exchange for benefits.
  • Problem interview: interview focused on the user’s past pains and workarounds.
  • Discovery call: sales call to qualify a live opportunity.

How to run founder-grade interviews

  1. Define the segment and the job. Write the core jobs to be done (JTBD) for your target: who, what job, outcome. Add a hard filter you can verify.
  2. Build a tiny screener. Create 3–5 items. Include a must-have behavior. Gate out students and consultants.
  3. Recruit fast. Use a short recruitment email and a calendar link. Use LinkedIn outbound or cold email for outreach. Incentive in the subject line if needed. Aim for 10 booked, 7 show, 5 usable.
  4. Set the room. 30 minutes. Camera optional. Ask for recording consent. Say you are not selling today. Promise to share a short summary.
  5. Run the interview. Warm-up, then last painful moment, current workaround, frequency, spend, decision circle, and WTP. Use the prompts below. Do not pitch.
  6. Close with a next step. Ask for artifacts, referrals, and permission to follow up. If qualified, offer a design-partner slot or a future pilot.
  7. Synthesize within one hour. Use the one-page note template. Tag: Pain, Trigger, Workaround, Criteria, Blockers, Budget/WTP, Quotes, Next step. Pull exact phrases into your copy.

Benchmarks

Use these directional ranges to judge if the promise lands during fast validation. Ranges reflect founder-led outreach. For channel specifics, see my LinkedIn outbound for founders guide.
Metric
good
typical
weak
Outreach reply rate
25–40% warm 10–20% cold
10–20% warm 5–10% cold
<10% warm <5% cold
Show-up rate
70–85%
60–70%
<60%
Interview length
30–40 min
20–25 min
<15 or >65 min
Usable interviews per segment
5–12
3–5
<3
You do not need 100 calls. Five to twelve per segment is enough to spot patterns when users are homogeneous. Directional but useful. Source: nngroup.com/articles/why-you-only-need-to-test-with-5-users/

Sample math. Email 60 warm contacts. 18 reply. 12 book. 9 show. 7 are usable. Four hours of calls. 90 minutes of synthesis. You get five repeat pains, two common workarounds, a fair price band of 49–99, and 14 quotes for your landing page.
In 90 seconds, find the bottleneck stopping your first 10 customers. Take the free quiz and get a personalized action plan.
Take the free quiz

Problem focus vs solution focus

When to use which: Problem focus is for mapping pains, workarounds, and buying triggers. Solution focus is for testing clarity and value on a concept or prototype.
Pros and cons: Problem focus reduces bias and fake positives. Solution focus speeds learning on messaging and UX but risks leading questions.
Decision rule: If you cannot describe the last painful moment and the current workaround with numbers and tools, stay in problem mode. If you can, move to solution mode and put a price in front of them.

Templates / examples

Recruitment email
Subject: 25-min research chat + $50 thank-you
Hi {Name} - I’m a founder working on {area}. Talking to {role} who {does job}. Could we do a 25-minute call this week? Not a sales call. I’ll share a one-page summary of findings. Thank-you gift: ${amount} or donation. Book here: {link}. If not you, who on your team owns this today?

Screener (3 items)
  • Which describes you best? {Role options}
  • When did you last {do target job}? {<7 days, <30, >30}
  • Which tool or workaround do you use today? {free text}

Consent snippet
“Is it OK to record this call for internal research so we can quote your words without your name? You can say no. We will store the file for up to 12 months and delete on request.”

30 prompts
  1. Tell me about your role and targets this quarter.
  2. What is the job you own that relates to {area}?
  3. When did you last do it?
  4. Walk me through the exact last time step by step.
  5. What triggered it?
  6. What made it annoying or risky?
  7. Who else was involved?
  8. What did you try first? Why?
  9. Where did it break?
  10. How did you fix it in the end?
  11. What do you use today? Tool, sheet, agency, person.
  12. What does it cost in money or time per month?
  13. What do you hate about that workaround?
  14. What do you like enough to keep?
  15. What would make you switch tomorrow?
  16. How often does this happen?
  17. What is the cost of doing nothing for a quarter?
  18. What is the best outcome when it goes right?
  19. What matters most when you pick a tool or vendor?
  20. What is a deal-breaker?
  21. Who signs it and who blocks it?
  22. What would be an unfairly low price? Why?
  23. A fair price most teams like yours would pay? Why?
  24. A price where you would hesitate? Why?
  25. What would have to be true to pay the higher price?
  26. If I had something that fixed {pain}, who else should I talk to?
  27. Can I see a recent invoice or screenshot of the workaround?
  28. If we run a pilot, what does success look like in 30 days?
  29. What would make you tell a friend about it?
  30. Who are 2 peers I should interview next?

One-page note template

Header: Interview #, Segment, Role, Company size, Date, Consent Y/N
Columns: Pain | Trigger | Workaround | Frequency | Cost | Criteria | Blockers | WTP | Quotes | Next step
Footer: Scores and decision: pursue / watchlist / drop.
Synthesis board
Columns: Pains, Workarounds, Triggers, Quotes, WTP bands, ICP notes, Next steps. Tag cards by segment. Collapse duplicates after 5–12 interviews.

Risks

  • Interviewing non-buyers. Add must-have behavior to screener.
  • Leading questions. Ask only about the past.
  • Mistaking interest for demand. Look for workarounds and spend.
  • No consent. Use a clear recording notice and safe storage.
  • Over-collecting. Stop at saturation (repeating insights) or after 12 good calls.
FAQ
  • You:
    How many interviews do I need?
    Guide:
    Five to twelve per segment is enough to spot patterns when users are similar.
  • You:
    Should I pay incentives?
    Guide:
    Yes for cold outreach and busy executives. $25–$100 is normal for 25–30 minutes.
  • You:
    Can I combine interviews and usability tests?
    Guide:
    Yes, but separate blocks. Problem first, then prototype.
  • You:
    What if users ask to see the product?
    Guide:
    Park it. Promise a separate session.
  • You:
    How do I document quotes legally?
    Guide:
    Get consent. Anonymize. Store recordings with limited access.
  • You:
    What if reply rates are low?
    Guide:
    Tighten the screener, improve the subject line, add a warm intro, or increase incentives.
  • You:
    Do I need a researcher?
    Guide:
    Not at seed. A focused founder with this guide is enough.
  • You:
    When do I stop?
    Guide:
    When new interviews repeat old insights.
Ready to stop guessing?
Book Your Free Strategy Call
© 2025
Telegram
Linkedin
Twitter
If you’re a funded B2B founder and want to check your customer interviews