Top 95 Probing Questions to Improve Your Sales

Conversely, probing questions also help you determine if your products and services aren’t a good fit. You can then move on to other leads in search of leads with more sales potential. Check out our tips for developing your qualifying skills and our comprehensive list of probing questions to help you get started.


Every sales professional need to know how to qualify a lead. It’s a fundamental part of the sales process that should never be ignored or overlooked. Not every lead you draw from your various marketing channels is going to convert to a sale. Some leads have problems in need of solutions that your product or service does not provide. Attempting to sell a poor-quality lead is beating the proverbial dead horse. 

How does a smart salesperson qualify their leads? It’s simple: learn to ask the right questions. Finding generic probing questions only requires a quick Google search, but developing your own questions is an acquired skill. Planning and practice while monitoring results are essential to creating your own custom probing questions. 

Why does developing your own probing questions matter? What you create for yourself will always have significantly more impact than scripted questions. Leads/potential customers need to hear belief and integrity from you, and that’s not easy to do reading from a page. 

The pay-off for your hard work is simple: the better you are able to develop promising leads, the more sales you will close. That’s something every sales representative would agree is mission-critical.

Here is a brief overview of what makes an effective probing question, as well as why they matter. Additionally, we’ve compiled a comprehensive list of questions to get you started on crafting your own.

Characteristics & Purpose Of Effective Probing Questions

The primary objective of an effective probing question is to gain useful qualifying information about leads. How you go about uncovering that information is what determines success or failure. The solution here is to ensure every question you ask to gain information is an effective probing question. Most sales teams brainstorm these questions together, though sometimes they are developed in tandem with marketing. Regardless of the process, any probing questions you integrate should all have the following characteristics:

  • Buyers should be able to understand questions and connect them to their own individual experiences.
  • Buyers should not feel as though they are being interrogated.
  • Responses to your questions should meaningfully contribute to presentation content that will speak to the buyer’s needs
  • Buyers should feel comfortable answering questions, not intimidated or uneasy
  • Effective probing questions should always lead to mutually beneficial results for sellers and buyers. Win-win is your endgame.

The purpose of probing questions can serve many different purposes, but the following items should be key objectives:

  • Confirm/change assumptions.
  • Gain new information.
  • Direct the conversation.
  • Get buy-in from your prospect and focus them on your products/services.
  • Tie-in with your sales story background.
  • Assist your potential buyers with seeing possibilities.
  • Clarify concerns, identify buying signals and gain commitment.
  • Demonstrate to the buyer that you have thoroughly researched their business, sector and industry.
  • Convey interest in the success of the buyer’s business.
  • Move the buyer through the sales process.

It is important to keep two things in mind as you compose these questions. Every question will need to be tailored to both your specific products/services and your ideal customer profile. With the right characteristics and purpose in mind, you should have your list of effective probing questions composed quickly.

Why Effective Probing Questions MatterWhy Effective Probing Questions Matter

Questions asked during qualifying fall into two categories: open and closed. Asking open-ended questions invites potential customers to share more about their business, their goals, and their needs. Closed questions cut you off from further inquiries and stymie your efforts to evaluate your leads. 

Effective probing questions should always be open-ended to establish and build rapport with potential buyers. The effectiveness of your probing questions is critical to closing deals and driving up sales revenue. Without them, your sales team spends needless amounts of time trying to sell to the wrong customers. 

Asking ineffective probing questions is like trying to sell someone the wrong size shoes: it hurts your long-term business (they bring them back), and it only creates more problems for the customer. Sales managers, marketing and sales representatives working inside and outside sales need to understand this clearly. Product and service knowledge is only useful if you know how to qualify potential customers effectively. Find the right fit the first time, and you will have a customer for life.

95 Probing Questions To Improve Your Sales95 Probing Questions To Improve Your Sales

We curated the following list to help you develop your own probing questions best suited to your products/services. Peruse them closely, and make notes regarding which ones are likely to be a good fit for your business.

  1. How can we help?
  2. Could you please give me some background to this?
  3. How much longer can you afford to have the problem go unresolved?
  4. Why are you seeking to do this work/project/engagement?
  5. Why isn’t this particular service/product/situation/issue working for you right now?
  6. How long has it been an issue/problem?
  7. How long have you been thinking about this?
  8. Can you tell me more about the present situation/problem?
  9. How is it impacting your organization/customers/staff?
  10. How much is the issue/problem costing you in time/money/resources/staff/energy?
  11. When you went to your existing supplier and shared your frustrations about this problem, what reassurances did they give you so 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 type 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. Have you used this type of product/service in the past?
  26. What are you currently doing to address the problem?
  27. What have you done in the past to address the problem?
  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. Who else is aware of it?
  32. What is it costing you?
  33. What is your strategy to fix this problem?
  34. Who supports this action?
  35. Is this problem causing other problems?
  36. What practical options do you have to address this?
  37. What kind of pressure is this causing you and the business?
  38. Does your competition have these problems?
  39. What goals and objectives do you have for this?
  40. What is your biggest challenge with this?
  41. How long have you been thinking about it?
  42. What has made you want to look into this now?
  43. What are your key objectives with this?
  44. In a perfect world, what would you like to see happen with this?
  45. What options are you currently looking at?
  46. What options have you tried?
  47. Do you have any preference with regard to the solution?
  48. What do you like about your current supplier?
  49. What kind of timeframe are you working within?
  50. How important is this need (on a scale of 1-10)?
  51. What is the biggest problem that you are facing with this?
  52. What other problems are you experiencing?
  53. Is there anything I have overlooked?
  54. What are you using/doing now?
  55. If you could have things the way you wanted, what would it look like?
  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. Do you know in what other areas the problem is costing you money?
  66. Can you give me an example?
  67. Can you be more specific?
  68. What other factors have we not discussed that are important to you?
  69. Are there any other areas I haven’t asked you about that are important?
  70. What sense of urgency do you have here?
  71. What else should I know?
  72. If you could design the perfect solution, what would it look like, how much would you spend, and how long would it go for?
  73. What are the long-term effects of the problem?
  74. What are the intangible effects of the problem?
  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. How does the problem ultimately affect your current customers?
  80. How does the problem ultimately affect your prospective customers?
  81. Can this problem affect productivity?
  82. How does the problem ultimately affect your sales teams?
  83. How does the problem ultimately affect your other employees?
  84. Can you see how this problem/issue can give your competition a competitive advantage?
  85. How does the problem ultimately affect your sales process?
  86. How does the problem ultimately affect your pricing/selling costs?
  87. Do you know what your competition is thinking/planning about this?
  88. How does the problem ultimately affect your reputation/goodwill/brand?
  89. If you were in your competitors’ shoes, how would you take advantage of this?
  90. If you were your competition, what would you do right now?
  91. Is this problem unique to your organization?
  92. Do they suffer the same problem?
  93. Is this an industry-wide problem?
  94. Is it a regional/geographic/demographic problem?
  95. How much does this problem cost you in man-hours/time?

Reference Link

Final thoughts

Final Thoughts

Develop effective probing questions for your qualifying process, and you will see increased sales. There is no dark secret or magic trick here. Every question you ask and every need or problem you discuss with your potential customers moves them closer to a buying decision. Take your time composing each question, and consult with marketing and your product knowledge specialists frequently. Soon enough, your research, hard work, and effort will be rewarded with better sales results and more satisfied customers.