30 Best Probing Questions For Sales to Use In Your Next Call

In my first article of this series, I spoke about how to structure your discovery meetings. In part two, we took a nosedive into what a successful meeting opening looks like with ILPA (Introduction, Last Time We Spoke, Purpose, Agenda. It’s now time to talk about probing questions in sales.

In this article, we’ll cover the following:


What is a Probing Question?

A probing question is a phrase used in sales that refers to a series of questions that sales representatives ask prospects to encourage deep thought about a matter before. These probing questions are designed to help gather more information on a particular topic.

By asking your prospects sales probing questions, you get to the heart of their problem and get a better understanding of how your solution will help better their situation.

What Are the Four Types of Questions?

There are four major types of questions commonly used in interviews and official business situations, these are:

  1. Open-ended questions.
  2. Specific questions.
  3. Motivation questions.
  4. Unconventional questions.

Open-ended questions

These are questions that do not require a specific answer. Answers vary because the probing questions often require a detailed explanation or a quick summary. They present an opportunity for the prospect to tell their story in detail and articulately.

When using open-ended questions in sales, ensure that the probing questions are specific to avoid the prospect from drifting from the topic. Examples of open-ended sales probing questions that sales reps may use include:

Tell me about your business. Why did you decide to get into this particular industry?

This question gives the prospect the chance to talk about their occupational history, what kind of jobs they had before, their motivating factor and what keeps them driven.

Loaded questions

These types of probing questions are designed to lead a prospect down a particular topic. They require the client to provide concrete and accurate details about the discussion at hand.

Specific questions are used during probing to get more detail into the prospect’s ambitions and expectations:

What options have you tried?

Here, the prospect is expected to clear details about any projects they may have attempted without yield or any techniques they may have tried out that didn’t work.

Closed-ended questions

These probing questions call for short definitive answers, usually as yes, no, or short phrases. Sales personnel use the questions during prospecting and lead qualification to gather factual data.

Examples of closed-ended questions include:

  • Do you have a budget?
  • Is this problem complicating other areas of your business?

NB: Avoid asking too many closed-ended questions quickly to avoid the prospect feeling like they are under interrogation.

Recall and process questions

A recall question requires the other person to remember a specific fact, while a process question triggers deep thought or analysis of said fact.

Below are some recall and process questions:

  • What CRM tools are you using now?
  • What three outcomes do you want from this?

What Are The Best Probing Questions?

Below are 30 of the tried-and-tested probing questions for sales we’ve proven that works.

1. How did you hear about our company?

This is a type of recall and process sales probing question used by sales reps during the lead qualification process. The data provides metrics that help in sales analysis, specifically to evaluate how well the company’s branding and advertising section is working.

2. How can we help?

This is an open-ended question and is used to get specific details about what challenges the prospect may be facing and how the sales rep can provide a solution using their service/product.

3. Could you please elaborate?

Here, sales reps use this probing question to get clarification on details that may not be clear. The information provided will help sales personnel analyze and find the root of the prospect’s pain point.

4. When did the situation begin?

Sales reps use this question to establish a timeline on how long the customer has been suffering and which techniques to use to mitigate the situation.

5. Has something like this ever happened before?

This is a relatively common probing question for sales reps because it helps them establish the problem’s severity and resolve it within the shortest time.

6. What methods have you tried to fix the situation?

The prospect’s answers will help guide the salesperson in the appropriate techniques and strategies to use.

7. Could you give me a few examples of what you mean?

By giving examples, sales reps can get a clear perspective of the customer’s problem and develop appropriate solutions.

8. What would be your ideal outcome from this situation?

This probing question encourages prospects to think critically about their expectations and what problems they need to be addressed.

9. Do you have a specific time-frame you would like us to work with?

Sales reps use this during probing to establish and manage the client’s expectations and formulate a strategy to use during the set time.

10. How long have you been thinking about this?

How long have you been looking for a solution since the problem started? Can you remember when the problem started and when you decided that you needed to take action?

11. How much is the issue costing you in terms of finances, time, and resources?

How much is the client losing every day while they attempt to solve the problem? How does it affect their workforce? How much time is spent trying to find solutions to no avail?

12. How did this problem begin?

When did you first notice that things weren’t going as planned? When did the first signs start appearing, and when did you realize that this problem could no longer go unsolved?

13. Why isn’t your current product/service not working for you?

What areas is the product/service you are using not addressing? What issues still haven’t been resolved?

14. How severe is the problem?

How is it affecting your workforce? Does it affect your company budget and other areas? How long have you been looking for an effective solution?

15. Why do you think you have been dealing with it for this long?

This is an excellent probing question for sales because it encourages the customer to reflect on the situation and discuss the issue.

16. What is your role in this issue/situation?

What part has the client played in the whole situation? Have they been trying to find solutions? Are they part of the problem?

17. What is your strategy to fix this issue?

Here sales reps use this probing question to get insight into what solutions or ideas the client may be thinking about.  They then can join forces in coming up with an adequate remedy.

18. Do your competitors face the same challenge?

Is the problem only within the client’s establishment? Is it a persistent issue even with other companies?

19. If you were your competitors, how would you solve this problem? What strategies would you use?


20. What are your expectations?


21. Why is it essential for you to come up with a solution?


22. What other problems are you facing besides this one?


23. How does the problem affect your company’s brand and image?


24. How does the problem affect your potential customers?

Does it affect your sales cycle? Do you have a more challenging time finding potential customers and qualifying them into prospects?

25. Have I missed anything?

Sales reps use this sales probing question to check for critical details they may have overlooked; the more thorough you are, the faster it is to develop a solution.

26. Do you have any questions or areas you may need to be addressed?


27. Is there anything else I should know?


28. Are there any areas that we should focus on?


29. Have I covered everything?


30. How soon would you like us to begin?

4 Tips On Asking Sales Probing Questions

As we remember from ILPA, we have already set the expectation that you will have questions for the prospect. This is to make sure what you share about your product/services will be applicable for them. You have also gained permission and agreement from your prospect that they are open to answering your questions because it will benefit them.

Sales probing questions help nurture cooperation between sales teams and prospects. By working together, both parties make the process of finding a practical solution easier and much faster.

Besides creating and nurturing cooperation between the sales reps and prospects, probing sales questions are excellent at improving the efficacy and effectiveness of sales strategies and techniques.

It always amazes me how sales reps know to “ask” questions but they typically have no direction or pre determined/thought out plan on how to ask these questions.

On a first call, regardless of what you’re selling, the questioning should always start the same. I like to start broad and then narrow down. I often see reps making the huge mistake of only asking leading questions that are not open-ended.

Knowing what sales probing questions are is half the journey. The other half is knowing how to use them effectively in sales. There are a few guidelines that salespeople should keep in mind when using probing questions on prospects and potential customers.

1) Steer clear of the word “or”

We want people to describe their goals and pains—not just answer yes/no or provide one-word answers. To do that, we need to understand the curse of the word “or.”

Which question will you get a better and more informative answer from?

What are some of the biggest challenges your department has getting projects out the door?


Is the biggest challenge for your department getting projects out the door the ease of collaboration or project management?

The first question is likely to give you a descriptive answer with lots of powerful data points. The second question will probably only give you a one-word answer with not much else. The language you use is incredibly powerful for uncovering important information.

Furthermore, this is the opportunity to build a good rapport with your prospects and show them how you might be able to “help” them (again not sell them).

2) Always (ALWAYS) Start with Your Prospect’s Role

By having a thoughtful and deliberate line of questioning, you have the guidance and outline to ask probing questions or dig in without losing your way.

Your line of questioning should always start with the following:

1) Tell me about your role. I have your title and I peeked at your LinkedIn profile. That’s not always indicative of everything you are responsible for!

2) Tell me a little about your team. How it is structured and where do you sit in the organization?

3) I purposefully ask this question broadly—what are you trying to accomplish as a team this year? What are the major initiatives that folks are working towards?

4) How is your team measured?

5) Are you going to hit those goals?

6) What happens if you do/don’t?

7) What top challenges do you face?

Asking someone to describe his or her role is hugely important in a sales process. It can give you insight into what they personally care about (the #1 reason why someone buys). It can also give you insight into additional responsibilities that you did not realize they had.

All of that data can be used to craft a compelling sales pitch that pulls on their personal heart strings.

3) Go Beyond LinkedIn to Research About Your Prospect/Their Team

Same goes for getting a better sense of their team and how it is structured. Every business is different and has quirks that cannot always be deciphered by just doing research using public information like LinkedIn.

Getting a sense of who is who in the zoo will give you a better idea of the biggest beneficiaries of your solution and who the ultimate decision maker or committee might be.

Besides LinkedIn, there are other channels of getting more insight into a prospect and their team. These include:

  • Their company website
  • The company’s mission statement
  • The company’s social media profile
  • Current customers
  • Blogs: try to read some of the blogs and articles your prospect reads or writes
  • Competitors: by looking up your prospect’s competitors you learn areas that they excel at and which ones need help.

4) Understand Your Prospect’s End Goal

Asking what the team is trying to accomplish is your first step to tying your solution to the overarching business goals. Sales probing questions are excellent at digging up this kind of information. By learning your prospect’s main objective, you get one step closer to coming up with an effective solution.

People buy products and services for personal reasons, but they always have to back up the purchase decision with how this will ultimately impact the business. If you can get initial insight into what those big goals are, you can use those as ammunition on why your solution is so critical. This is essential to overcoming potential objections.

We have all heard prospects use the excuse “We don’t have the budget” or “Not good timing.” When you have taken the time to understand their business goals, you have ammunition to challenge and push back.

Try something like this:

“Mr. Prospect, if you are open to be challenged a bit here. You mentioned that you are trying to grow your top funnel leads by 50% this year. But, your current resources are spending 25% of their time just trying to report on goals. I have showed you how our software can enable your team to re-allocate that 25% back to executing projects so that you can ensure you hit your 50% lead gen goal. I would think this is perfect timing given that there are only 6 months left in the year and you’re only at 10% growth.”

Use This Data to Challenge Your Customer

Your line of questioning and starting broad provide massive advantages to connecting your products and services to business and personal needs. There are nuances to the additional questions that you ask based on what you’re selling.

Ensuring you always start with the above fundamental questions will give you ample information to make your sales pitch compelling and galvanize your prospect to take action NOW.

Emily Meyer is a tenured sales rep that has been selling in the high-tech industry for 10 years. Her secret sauce to success has always been a genuine curiosity and desire to truly help her customers solve complex business problem which in turn will make them look good internally. Emily is dedicated to sales process and believes strongly that sales is 70% learned and 30% innate ability. She strives to continue to hone her craft and also pay it forward to the younger generations of sales reps through teaching and mentorship.

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