100 Sales Probing Questions to Truly Understand Your Prospects’ Pain [Infographic] | Sales

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A successful career in is dependent on your ability to ask good discovery questions. And to develop that skill fully, you must know when it’s time to dig deeper with probing questions. You know the kind: the type of questions necessary to uncover your prospect’s core needs — fast.

In these cases, simply asking, “Tell me about your biggest challenges with your current solution,” and moving on isn’t enough. You must probe with follow-up questions that will give your prospect the confidence to share their real hurdles they’re facing.


Here’s a comprehensive list of 100 probing sales qualifying questions you can ask buyers to get intimately familiar with their situation and formulate potential solutions. If you’d like my complete list of 450 sales questions for every situation, download this ebook.

And, don’t forget: probing questions are as much about listening as they are about speaking. Make sure you’re really listening to your prospect’s responses, so you know just which question to ask next.

More of a visual person? Click here to skip to the below.

Sales Probing Questions

  1. How can we help?
  2. Could you please give me some background to this?
  3. Why are you seeking to do this work/project/engagement?
  4. Why isn’t this particular service/product/situation/issue working for you right now?
  5. Can you tell me more about the present situation/problem?
  6. How long has it been an issue/problem?
  7. How long have your been thinking about this?
  8. How is it impacting your organization/customers/staff?
  9. How much is the issue/problem costing you in time/money/resources/staff/energy?
  10. How much longer can you afford to have the problem go unresolved?
  11. When you went to your existing supplier and shared your frustrations about this problem, what reassurances did they give you that it wouldn’t be repeated?
  12. How did these problems/issues first come about? What were the original causes?
  13. How severe is the problem?
  14. Why do you think the issue/problem has been going on for so long?
  15. When do you need the issue/problem fixed by?
  16. What kind of return or payoff will you be looking for if you get a successful resolution of the problem?
  17. How often do you think the problem has come up where you weren’t even aware of it?
  18. Who is ultimately responsible for this?
  19. Tell me more about it.
  20. Can you make an educated guess as to how much it costs you?
  21. Why have you been dealing with this for so long?
  22. Why do you think it is happening?
  23. What’s your role in this situation/issue/problem?
  24. What bothers you the most about this situation/issue/problem?
  25. What are you currently doing to address the problem?
  26. What have you done in the past to address the problem?
  27. Have you used this type of product/service in the past?
  28. Does this affect other parts of the business?
  29. What has prevented you from fixing this in the past?
  30. What kind of timeframe are you working in to fix this?
  31. How long have you been thinking about it?
  32. Who else is aware of it?
  33. What is it costing you?
  34. What is your strategy to fix this problem?
  35. Who supports this action?
  36. Is this problem causing other problems?
  37. What practical options do you have to address this?
  38. What kind of pressure is this causing you and the business?
  39. Does your competition have these problems?
  40. What goals and objectives do you have for this?
  41. What is your biggest challenge with this?
  42. What has made you want to look into this now?
  43. In a perfect world, what would you like to see happen with this?
  44. What are your key objectives with this?
  45. What options are you currently looking at?
  46. What options have you tried?
  47. What do you like about your current supplier?
  48. What kind of timeframe are you working within?
  49. How important is this need (on a scale of 1-10)?
  50. What is the biggest problem that you are facing with this?
  51. What other problems are you experiencing?
  52. What are you using/doing now?
  53. If you could have things the way you wanted, what would it look like?
  54. Do you have any preference with regards to the solution?
  55. Is there anything I have overlooked?
  56. Have I covered everything?
  57. What alternatives have you considered?
  58. Have you got any questions you’d like to ask me?
  59. What is important to you in finding a solution to this?
  60. What are your top three requirements that this solution just has to have?
  61. How soon would you like to move with this?
  62. What three key outcomes do you want from this?
  63. How does this look/sound/feel to you?
  64. Can you please tell me about that?
  65. Can you give me an example?
  66. Can you be more specific?
  67. What other factors have we not discussed that are important to you?
  68. Are there any other areas I haven’t asked you about that are important?
  69. What sense of urgency do you have here?
  70. What else should I know?
  71. If you could design the perfect solution, what would it look like, how much would you spend, and how long would it go for?
  72. What are the long-term effects of the problem?
  73. What are the intangible effects of the problem?
  74. Do you know in what other areas the problem is costing you money?
  75. Can you put an amount on the problem in terms of cost: Weekly, monthly, annually?
  76. Can you see how much money you/your organization loses every day by not solving this issue?
  77. Does the issue cause problems with employee morale?
  78. Does the issue cause problems that negatively affect the motivation of your staff?
  79. Can this problem affect productivity?
  80. How does the problem ultimately affect your current customers?
  81. How does the problem ultimately affect your prospective customers?
  82. How does the problem ultimately affect your sales teams?
  83. How does the problem ultimately affect your other employees?
  84. How does the problem ultimately affect your sales process?
  85. How does the problem ultimately affect your pricing/selling costs?
  86. How does the problem ultimately affect your reputation/goodwill/brand?
  87. Can you see how this problem/issue can give your competition a competitive advantage?
  88. If you were in your competitors’ shoes, how would you take advantage of this?
  89. If you were your competition, what would you do right now?
  90. Do you know what your competition is thinking/planning about this?
  91. Do they suffer the same problem?
  92. Is this problem unique to your organization?
  93. Is this an industry-wide problem?
  94. Is it regional/geographical/demographical?
  95. How much does this problem cost you in man hours/time?
  96. How much more productive could your people be if problem did not exist?
  97. So what type of a number would you put on this issue in terms of prioritization?
  98. Looking at this from a point of lost sales, how much is just one sale worth to the company?
  99. Who did you work with last time and why?
  100. Have I asked you about every detail that’s important to you?

100 Sales Questions to Understand Your Prospects’ Pain (1).jpg

This is an excerpt taken from the ebook “450 Sales Questions: What to Ask in Any Situation.” It is published here with permission.

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