25 Discovery Questions That Turn Small Talk Into Sales

If your discovery calls sound more like an interrogation than a conversation, you’re leaving deals (and credibility) on the table. The best salespeople don’t just tick boxes; they uncover problems their prospects didn’t even know they had.

The secret?

Ask questions that make them stop, think, and share. Not “yes/no” traps. Not robotic scripts. Real, open-ended questions that pull the story out of them.

Here are 25 proven questions you can plug straight into your next discovery call. Use them to dig deeper, earn trust, and position yourself as the person who understands their world better than anyone else.

The Discovery Questions

1. “Walk me through how you’re currently handling [X process] from start to finish.”

2. “What’s been working well for you in [X area],

and what’s been more of a struggle?”

3. “If nothing changed in the next 6 months, what would that mean for you and your team?”

4. “How do you measure success in this area right now?”

5. “What led you to start exploring solutions like this?”

6. “Who else is involved in making decisions about [X]?”

7. “When [X problem] happens, what’s the usual impact on your day-to-day?”

8. “Tell me about the last time this issue came up, how did you handle it?”

9. “If you could wave a magic wand and fix [X], what would it look like?”

10. “What’s prompting you to look at this now instead of 6 months ago, or 6 months from now?”

11. “How is this challenge affecting your team’s ability to hit their targets?”

12. “What have you already tried to solve this?”

13. “If this goes well, what does a win look like for you personally?”

14. “Where does this sit in your overall list of priorities?”

15. “What’s the cost of doing nothing about this?”

16. “Who feels this problem the most inside your organisation?”

17. “If budget wasn’t a factor, what would your ideal solution include?”

18. “How have you handled similar challenges in the past?”

19. “What’s the ripple effect if this problem isn’t solved?”

20. “What kind of feedback are you getting from your customers or team about this?”

21. “If we were having this conversation again in 12 months, what would need to have happened for you to feel happy with the outcome?”

22. “How does this issue impact other departments or parts of the business?”

23. “What’s stopping you from fixing this today?”

24. “If you had to choose one area to improve first, what would it be?”

25. “What’s the biggest risk for you in making a change?”

Final Tip: Pick 2–3 of these questions and drill them with a partner or run AI roleplays in Pixaro every day for a week. Muscle memory is what turns “Uh…” into a confident, natural conversation. Start your free trial here!