Customer Discovery Questions: 60 Questions for Early-Stage Startups

Customer Discovery Questions: 60 Questions for Early-Stage Startups

Customer discovery is where early-stage startups either get lucky on purpose or wander into a product that only sounds good inside the team chat.

A good discovery interview feels less like “research” and more like a sharp, curious conversation. You are trying to understand what people already do, what hurts, what they pay attention to, and what would make them change their behavior. Not someday. This month.

This guide gives you 60 customer discovery questions you can reuse for almost any early-stage startup, plus a simple way to run the interview without turning it into a sales call.

What customer discovery is really for

Customer discovery is not about collecting opinions like “That’s cool” or “I would use this.” Those answers are cheap. They cost the person nothing to say.

You want specifics. Stories. Recent examples. The last time they faced the problem. How they solved it. What broke. What it cost them in time, money, or stress.

When you get that level of detail, you start seeing patterns. Patterns become positioning. Positioning becomes a product that makes sense to real humans.

How to run the interview without making it weird

Start the interview with context, not a pitch. A simple opener works: “I’m talking to a few people to understand how you handle X today. I’m not selling anything. I just want to learn from how you do it.”

Then ask for a walkthrough of a real, recent situation. “Tell me about the last time…” is one of the highest ROI sentences in startup history.

When they answer, slow down. If something sounds painful, ask what happened next. If they mention a workaround, ask why they built it. If they say “it depends,” ask what it depends on. Your best insights usually live inside those follow-ups.

How to use the questions below

Do not try to ask all 60 in one call. Pick 10 to 15 that fit your goal, then go deep. Depth beats breadth almost every time.

The questions are grouped by theme so you can quickly choose what you need. If you are validating a problem, focus on workflow and pain. If you are exploring pricing, focus on impact and buying behavior. If you are trying to find urgency, focus on triggers and priorities.

60 customer discovery questions

A) Background and context

These questions help you understand who they are, what they own, and what “success” looks like in their world.

1. Can you tell me about your role and what success looks like for you?

2. What are you responsible for day to day?

3. What goals are you focused on this month or quarter?

4. What does a good week look like in your work?

5. What does a bad week look like in your work?

6. Who do you work with most closely?

7. What tools or systems do you rely on the most?

8. What constraints do you deal with (time, budget, approvals, policy, skills)?

B) Current workflow

This section is the backbone. If you understand the workflow, you understand what “better” means.

9. Walk me through the last time you did this task from start to finish.

10. What usually triggers you to start this process?

11. What is the first step you take?

12. What are the steps that take the most time?

13. Where do things usually get stuck?

14. What information do you need, and where does it come from?

15. Who else needs to be involved, and when?

16. What do you track, measure, or report during this process?

17. What happens when something changes mid-way?

18. What does “done” look like for this workflow?

C) Pain points and impact

Here you are not collecting complaints for fun. You are mapping real cost and real consequences.

19. What is the hardest part of this process?

20. What feels most annoying or repetitive?

21. What mistakes happen most often?

22. What causes delays?

23. What parts require the most back and forth with others?

24. What is the cost of this problem (time, money, missed opportunities, stress)?

25. What happens if you do nothing and just keep the current approach?

26. Who is most affected when this goes wrong?

27. How often does this problem happen?

28. When was the last time it happened? What happened?

29. What is the worst case scenario when this fails?

30. What would improve your day the most if it suddenly worked better?

D) Workarounds and alternatives

Workarounds are proof of demand. People do not create hacks for problems they do not care about.

31. How are you solving this today?

32. What workarounds have you created?

33. What spreadsheets, docs, or templates do you use?

34. What tools have you tried for this in the past?

35. What did you like about those tools?

36. What did you dislike or what was missing?

37. If you could wave a magic wand and change one thing, what would it be?

38. What do you wish you had visibility into, but cannot see today?

39. What do you do when you need this done quickly?

40. Who do you ask for help, and what do they do for you?

E) Priority and urgency

A problem can be real and still not matter right now. This section tells you where it sits in their mental stack.

41. Where does this sit on your priority list compared to other problems?

42. What makes this problem feel urgent?

43. What makes it not urgent?

44. What event would force you to fix this now?

45. What would you need to believe to switch to a new solution?

46. What would block you from switching?

47. What risks do you worry about with new tools or new processes?

48. If a solution saved you time, where would that time go?

49. What would you stop doing if this were solved?

50. How would you know the solution is working in the first month?

F) Buying and decision-making

Even in tiny startups, purchases have gravity: budget, trust, approvals, and perceived risk.

51. Have you paid for something similar before? What was it, and why did you buy it?

52. Who is involved in approving a new tool or budget?

53. What does the approval process look like step by step?

54. What matters most when choosing a solution (price, security, support, integrations, ease)?

55. What is a must have requirement for you?

56. What is a deal breaker requirement for you?

G) Gentle solution exploration

You can explore solutions without pitching. Keep it hypothetical and focused on expectations.

57. If you had a better option, what would you expect it to do, in your words?

58. What would make you trust that it actually works?

59. How would you compare two options and decide which one wins?

60. If you could start from scratch, how would you design the ideal workflow?

Follow-up prompts that unlock real answers

Most people start with broad statements. Your job is to pull the thread until you get a concrete example.

These follow-ups work in almost every interview: “Can you tell me about the last time this happened?” “What happened right after that?” “Why was that difficult?” “What did you try first?” “How did you decide that was good enough?” “Who else was involved?” “What did it cost you in time or stress?”

When you get a story with timestamps, tools, steps, and tradeoffs, you are in the good stuff.

Common mistakes that make discovery interviews useless

A classic trap is asking future-tense questions like “Would you use this?” People are optimistic in theory and busy in real life. Another trap is pitching mid-interview. The moment you pitch, the person switches into “be nice” mode, and you stop learning.

It also hurts to mix personas in one conversation. A user, a manager, and a buyer can describe the same problem in three different languages. Keep each interview focused on one viewpoint, then compare patterns across interviews later.

Finally, do not treat one strong opinion as truth. Discovery is about frequency, not volume. You want to know what keeps showing up.

Turning interviews into decisions

After about 8 to 12 interviews, you should be able to write a one-page summary that feels clear and slightly uncomfortable, because it forces choices.

Capture the top pains in the exact words you heard. Note the workarounds people built. Identify what triggers urgency. Write down the must-haves and deal breakers. Map how buying decisions happen and who is involved.

If you can write that page, you can write a landing page that does not rely on hype. You can also build a roadmap that is driven by reality, not vibes.

Final thought

Customer discovery is not glamorous, but it is wildly powerful. It replaces guesswork with evidence and turns “I think” into “I know because I heard it 9 times.”

If your team is doing lots of interviews, it can help to automate the heavy admin stuff like sending invites, scheduling, reminders, transcripts, and summaries. That is exactly the kind of workflow we build at Askiva, so founders and researchers can spend more time learning and less time chasing calendars.

The universe is complicated. Your customers are too. Go talk to them anyway.