50 Probing Questions For Sales Conversations


Open ended sales questions are the pinnacle of healthy sales conversations. Questions and probing techniques help buyers make purchasing decisions, without you needing to pitch or sell to them. The fact that the discovery stage is often pointed to as THE most crucial stage of the sales process, highlights the importance of sales people being able to ask effective questions.

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Thinking of the right questions to ask at the right time can be challenging however. That’s why we’ve put together a list of some our favourite probing questions and open ended questions that can be used in your sales conversations today:

  1. Why are we talking today? (assuming they asked for the meeting)
  2. Can you tell me more about your role at ABC company?
  3. How many people in your team?
  4. What are the people you manage responsible for and what targets do they have?
  5. How many of them meet that target versus miss it?
  6. For those that miss it, what does that look like in terms of time/money?
  7. What metrics and goals are you responsible for day-to-day?
  8. What are your top objectives for the upcoming quarter?
  9. Why are those priority objectives for this quarter?
  10. Can you walk me through the process as it looks today?
  11. What do you feel is the most crucial/problematic stage in that process?
  12. What problem are you trying to solve?
  13. What do you think is causing that problem?
  14. Why are you looking at solving this problem now?
  15. Why haven’t you done anything about that problem before now?
  16. What are the knock on effects if you don’t solve this problem?
  17. How do these knock on effects impact you personally?
  18. What would it mean for you personally if you managed to solve these problems?
  19. Can you tell me more about that?
  20. In an ideal world, what would you want to be doing?
  21. What other solutions or products have you looked at?
  22. What did you like about those other solutions?
  23. What did you feel those other solutions were missing?
  24. What would you say is a ‘must-have’ in a solution?
  25. How do you feel your team would respond to this solution?
  26. What does success look like in the first 6 months/year?
  27. If I could demonstrate how we could help you address this challenge, how much of a favourable position would that put us in?
  28. If you don’t go ahead with implementing a solution like ours, is ‘doing nothing’ a feasible solution?
  29. Can you help me understand what you mean by that?
  30. Sorry, I didn’t quite get what you mean by that. Can you just go over that again?
  31. Can you give me an example of that?
  32. On a priority list, where would this currently sit?
  33. What does the decision making process look like when procuring solutions like ours?
  34. Who else is this important to?
  35. Who would be the person who signs the order form?
  36. What concerns do you feel the person who signs the order form would have about this?
  37. Would it make sense to involve the person who signs the order form in our conversations?
  38. How will this be funded?
  39. Is there a budget for this?
  40. Do you have the final say on spending that budget?
  41. What will be the main factors in making a decision?
  42. You mentioned you weren’t having a good experience with your current provider. What do you hope we will do differently should we work together?
  43. If you didn’t feel we were the right solution for you, are you happy to be transparent and tell me?
  44. When would you want to make a decision by?
  45. What do you foresee as the potential blockades and hurdles we will face along the way in partnering with you?
  46. How can I help you avoid hitting these?
  47. Is this decision a local one or more widespread?
  48. Why would this only be relevant to your team?
  49. Would you agree that moving to this next stage in the process makes sense?
  50. Can we schedule in a time right now to talk again?

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