144 Probing Questions to Help You Close More Deals

Your ability to close deals and lead customers through the sales cycle depends on the quality of the probing questions you ask.

Probing questions could also be called discovery questions and is a skill that, unfortunately, many sales professionals lack in their sales process.

The ability to ask good probing questions relies on active listening and really having the desire to understand the customer’s core need.

Probing Questions: The Basics

When asking sales probing questions, we are trying to add depth to the conversation. We want to find more about the answer the prospect has just given by asking questions such as “Can you give me an example?” or “What would your ideal outcome be?” or “Could you tell me what you mean by {x}?”.

For perhaps a more relatable example, consider the following scenario:

When you ask your best friend how their day has been, and they respond with “good” – that is only a surface-level response. By asking probing questions such as:

• Why was your day good?
• What was it about the thing that made your day good?
• How did the thing that made your day good make you feel?

You are adding depth to the conversation. You are probing for more information.

In sales, we should be doing the same.

Read more below to find a list of over 100 sales probing questions. These probing questions are designed to get your customer to think more deeply about the problem and what needs to be addressed.

Remember to listen intently when asking theses probing questions so you know exactly what to ask next. You want to build the pain, so the customer will be inspired to act sooner.

Rapport Building Sales Questions

Building rapport is essential for any successful salesperson. These are the general chit-chat questions to break the ice and provide some familiarity at the day’s start. Ask questions about the customer’s day, life and interests to get them talking more.

1. “How was your weekend?”
2. “What kind of hobbies do you have?”
3. “What did you do before this job?”
4. “What inspired you to get into {industry} in the first place?”
5. “Do you have any plans for {season}?”
6. “What do you like most about your job/role?”
7. “How has the year been so far in terms of business?”
8. “What is something you’re proud of that your organization has done recently?”

Sales Probing Questions

Once you have built some rapport, it’s time to dig into the customer’s pain points and motivations. Here you are looking to find out key information about your prospect. You want to ask probing questions to clarify the customer’s challenges. Asking a challenging probing question can go a long way to help the customer understand their own pains.

1. “How can we help?”
2. “Do you have a need to be addressed?”
3. “Could you please give me some background to this?”
4. “Can you tell me more about the present situation/problem?”
5. “Tell me more about it.”
6. “How much is the issue impacting your business?”
7. “How long have you been thinking about this?”
8. “Why do you think it is happening?”
9. “What goals and objectives do you have for this?”
10. “What is your biggest challenge with this?”
11. “What are your key objectives with this?”
12. “What do you like about your current supplier?”
13. “What are you using/doing now?”
14. “Do you have any preference with regards to the solution?”
15. “What three key outcomes do you want from this?”
16. “Can you please tell me about that?”
17. “Can you give me an example?”
18. “Can you be more specific?”
19. “How does this look/sound/feel to you?”
20. “Why are you seeking to do this work/project/engagement?”
21. “What outcomes do you need to achieve?”
22. “What would be your ideal outcome?”

Probing Questions for Identifying and Dig Deeper into Problems

These probing questions are designed to help you break through the barriers your prospect might face. Here you want to know how severe is the problem to get them to the next stage of the sales process.

The following probing questions will help you identify the priorities in the business and it affect.

1. “How can we help?”
2. “Could you please give me some background to this?”
3. “Can you tell me more about the present situation/problem?”
4. “Tell me more about it.”
5. “How long have you been thinking about this?”
6. “Why do you think it is happening?”
7. “What goals and objectives do you have for this?”
8. “What is your biggest challenge with this?”
9. “What are your key objectives with this?”
10. “What do you like about your current supplier?”
11. “What are you using/doing now?”
12. “Do you have any preference with regards to the solution?”
13. “What three key outcomes do you want from this?”
14. “Can you please tell me about that?”
15. “Can you give me an example?”
16. “Can you be more specific?”
17. “How does this look/sound/feel to you?”
18. “Why are you seeking to do this work/project/engagement?”

Questions For Identifying Symptoms For Big-Picture Problems

The following sales questions are designed to help you identify the barriers your prospect is facing. Understanding what, how, and how long these issues have been present will help you get to the root of the problem.

The root of these barriers is more than likely showing up in other areas in their business or personal development. These questions will help you to identify which issues need to be addressed first.

1. “Why isn’t this particular service/product/situation/issue working for you right now?”
2. Could you give me an example?
3. “How long has it been an issue/problem?”
4. “Why do you think the issue/problem has been going on for so long?”
5. “How much longer can you afford to have the problem go unresolved?”
6. “How is it impacting your organization/customers/staff?”
7. “How severe is the problem?”
8. “When do you need the issue/problem fixed by?”
9. “Why have you been dealing with this for so long?”
10. “What bothers you the most about this situation/issue/problem?”
11. “What has prevented you from fixing this in the past?”
12. “What kind of timeframe are you working in to fix this?”
13. “How long have you been thinking about it?”
14. “Is this problem causing other problems?”
15. “Does your competition have these problems?”
16. “What is the biggest problem that you are facing with this?”
17. “What other problems are you experiencing?”
18. “What alternatives have you considered?”
19. “What are the intangible effects of the problem?”
20. “Does the issue cause problems with employee morale?”
21. “Does the issue cause problems that negatively affect the motivation of your staff?”
22. “Can this problem affect productivity?”
23. “Is this problem unique to your organization?”
24. “Is this an industry-wide problem?”
25. “Is it regional or geographical?”
26. “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?”
27. “How did these problems/issues first come about? What were the original causes?”
28. “What have you done in the past to address the problem?”
29. “Does this affect other parts of the business?”
30. “What kind of pressure is this causing you and the business?”
31. “What options have you tried?”
32. “What are the long-term effects of the problem?”
33. “How does the problem ultimately affect your current customers?”
34. “How does the problem ultimately affect your prospective customers?”
35. “How does the problem ultimately affect your sales teams?”
36. “How does the problem ultimately affect your other employees?”
37. “How does the problem ultimately affect your sales process?”
38. “How does the problem ultimately affect your reputation/goodwill/brand?”
39. “Do you feel this problem/issue has given your competition a competitive advantage? If so, how?”
40. “Who did you work with last time and why?”
41. “How often do you think the problem has come up when you weren’t aware of it?”
42. “What are the long-term effects of the problem? How would you take advantage of this if you were in your competitors’ shoes?”
43. “Do you know what your competition is thinking/planning about this?”
44. “Do they suffer from the same problem?”
45. “Does this affect other parts of the business?”

Examples of Probing Questions for Prospect Actions

Once you have asked the best probing question to understand the barriers the customer might be facing, the next step is to understand what actions your prospect should take.

These examples of probing questions will help the customer see the specific details on the road to improving their business with your particular product.

Here you want to begin the process of outlining details and actions that will benefit them.

1. “What number would you put on this issue in terms of prioritization?”
2. “How much more productive could your people be if the problem did not exist?”
3. “If you were your competition, what would you do right now?”
4. “If you could design the perfect solution, what would it look like, how much would you spend, and how long would it go for?”
5. “What sense of urgency do you have here?”
6. “What three key outcomes do you want from solving the problem?”
7. “What are your top three requirements that this solution just has to have?”
8. “If you could have things the way you wanted, what would it look like?”
9. “What are you using/doing now?”
10. “How important is this need (on a scale of 1-10)?”
11. “What options are you currently looking at?”
12. “In a perfect world, what would you like to see happen with this?”
13. “What is your strategy to fix this problem?”
14. “What are you currently doing to address the problem?”

Probing Questions on Budget and Resources

These probing questions focus on budget and resources, allowing you to understand better where the prospect is financially positioned. Budget is a hurdle that must be overcome at some stage in the sales process so the question examples at that point when discussing with the prospect.

1. “We’ve got several options available; what were you looking to pay so I can match the right solution at the right price for you, just a ball park…” (Say “Just a ball park” very casually as though it’s no big deal)
2. “Have you got a ball-park figure in mind? Just a ball park…” (Say “Just a ball park” very casually as though it’s no big deal)
3. “What are you working with at the moment? Just a ball park…” (Say “Just a ball park” very casually as though it’s no big deal)
4. “Have you got budget approval for this already?”
5. “How do you handle budget considerations?”
6. “How will this product/project get funded?”
7. “What sort of budget do you have in mind?”
8. “What are you looking to pay for this?”
9. “We’ve got some options available; what were you looking to pay so I can match the right solution at the right price for you?”
10. “Is there a budget allocated for this project?”

Probing Questions to Understand Possible Roadblocks

When working with customers, it’s a good idea to ask probing sales questions to understand possible roadblocks that might prevent prospects from going ahead with your solution.

By asking the right questions around potential barriers, you won’t be affected by anything unexpected, as you’ll have covered everything with these effective probing questions.

1. “What obstacles do you see that would prevent this project from going forward?”
2. “Is there anything we haven’t discussed which could get in the way?”
3. “In the past, what has occurred to derail potential projects like this?”
4. “What do you estimate the probability is of this going ahead?”
5. “Have I covered everything you need to know? What, if anything, do you additionally need to hear from me?”
6. “Is there anything happening in the company at the moment that might jeopardise this?”
7. “What are your thoughts so far?”
8. “Do you have any concerns at this stage?”
9. “What are the restrictions on this project, from your side?”
10. “Does what I’ve said sound like what you have in mind?”

Gaining Clarity of Responsibility Probing Questions

When selling, it’s a good idea to get a deeper understanding of the customers’ decision-making process and who else might be involved in that.

These sales probing questions are useful at the end of the customer meeting to understand if there is anything else to cover off before getting the proposal together and presenting solutions.

1. “Who is ultimately responsible for this?”
2. “Why are you seeking to do this work/project/engagement?”
3. “Who else is aware of it?”
4. “What has made you want to look into this now?”
5. “What kind of timeframe are you working within?”
6. “Is there anything I have overlooked?”
7. “Have I covered all issues?”
8. “What alternatives have you considered?”
9. “Do you have any questions you’d like to ask me?”
10. “What other factors have we not discussed that are important to you?”
11. “Are there any other important areas I haven’t asked you about?”
12. “What else should I know?”
13. “Have I asked you about every important detail to you?”
14. “How soon would you like to move with this?”
15. “Does this affect other parts of the organization?”
16. “What’s your role in this situation/issue/problem?”
17. “Who supports this action?”

The Probing Question is Essential for an Effective Sales Strategy

Sales is all about asking questions. I’d go so far as to say the probing question is selling. You want open-ended questions to ask to really begin to understand and gain insight into your prospect’s problems.

So, use probing questions to start selling better, and ask open ended questions to get your prospects thinking about ways that you can help fix their problem.

This skill alone will go a long way to helping you boost your revenue numbers and get the answers you need.

Take the first step and learn these probing questions today!