50 Questions to Uncover Real Pain Points

The quality of your user research depends entirely on the quality of your questions. Bad questions get polite lies. Good questions get actionable truths.

Here are 50 battle-tested questions organized by category, all designed to pass The Mom Test and uncover real pain points.

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Understanding the Problem

These questions help you understand if a problem is real and painful enough to solve.

1. "What's the hardest part about [doing X]?"

2. "Can you tell me about the last time that happened?"

3. "Why was that hard?"

4. "How often does this problem come up?"

5. "What does this problem cost you?" (time, money, stress, reputation)

6. "What happens if you don't solve this?"

7. "Who else is affected when this problem occurs?"

8. "On a scale of 1-10, how painful is this? Why that number?"

9. "If you could wave a magic wand and fix one thing about [X], what would it be?"

10. "What would your life look like if this problem didn't exist?"

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Current Behavior & Solutions

These questions reveal what people actually do (vs. what they say they'd do).

11. "How are you solving this today?"

12. "Walk me through your current process step by step."

13. "What tools do you currently use for this?"

14. "How much time do you spend on this per week?"

15. "What do you like about your current solution?"

16. "What don't you like about it?"

17. "Have you tried anything else? What happened?"

18. "Why did you choose your current approach over alternatives?"

19. "If your current tool disappeared tomorrow, what would you do?"

20. "When was the last time you looked for a better solution?"

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Motivations & Goals

These questions uncover the deeper "why" behind behavior.

21. "What are you ultimately trying to achieve?"

22. "Why is that important to you?"

23. "What would success look like?"

24. "How does your boss/team measure success on this?"

25. "What's stopping you from reaching that goal right now?"

26. "What would change in your work if you solved this?"

27. "How does this problem affect your team/company?"

28. "What's at stake if you don't figure this out?"

29. "Is this something you're actively trying to solve, or just living with?"

30. "What made you start looking for a solution?"

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Decision Making & Buying

These questions help you understand how decisions get made.

31. "If you found a perfect solution today, what would happen next?"

32. "Who else would need to be involved in this decision?"

33. "What would make this a no-brainer decision for you?"

34. "What concerns would you have about trying something new?"

35. "How do you typically evaluate new tools?"

36. "What's your budget for solving this problem?"

37. "Have you paid for something similar before? What was it?"

38. "What would make you switch from your current solution?"

39. "What would be a deal-breaker for you?"

40. "How quickly would you need to see results?"

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Digging Deeper

These follow-up questions help you get past surface-level answers.

41. "Can you give me a specific example?"

42. "What do you mean by [term they used]?"

43. "Why do you think that is?"

44. "How did that make you feel?"

45. "What happened next?"

46. "Is there anything else I should know about this?"

47. "What question should I have asked but didn't?"

48. "Who else should I talk to about this?"

49. "What surprised you most about dealing with this problem?"

50. "If you were building a solution, where would you start?"

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How to Use These Questions

Don't Use Them as a Script

These questions are starting points, not a checklist. Listen to answers and follow the conversation naturally.

Pick 5-7 Core Questions

For each research project, select the questions most relevant to what you're trying to learn.

Always Follow Up

The magic happens in follow-up questions. When someone says something interesting, dig deeper: "Tell me more about that."

Adapt to the Conversation

If the person mentions something unexpected, explore it. The best insights often come from unplanned directions.

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Questions by Research Stage

| Stage | Goal | Best Questions | | --- | --- | --- | | Problem Discovery | Find if problem exists | #1-10 | | Solution Validation | Understand current solutions | #11-20 | | Persona Research | Understand motivations | #21-30 | | Go-to-Market | Understand buying process | #31-40 | | Any Stage | Get deeper insights | #41-50 |

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Questions to Avoid

These questions invite polite lies. Stick to questions about past behavior and current reality.

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Key Takeaways

1. Ask about the past, not the future — "When did you last..." beats "Would you ever..."
2. Focus on behavior, not opinions — What people do matters more than what they say
3. Dig into specifics — "Tell me about the last time" forces real stories
4. Follow the energy — When someone gets animated, explore that topic
5. End with expansion — "Who else should I talk to?" grows your research

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