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. Its now time to talk about probing questions in sales.

The following are some of the topics covered in this article:

  • What is a Probing Question?
  • There are four types of questions: factual, interpretive, evaluative and practical. Factual questions ask for a piece of information or what someone has done in the past.
  • What are the best probing questions for sales?
  • You should never assume that you know the right questions to ask your salespeople.
  • With this data, we can see that a company’s customer base is most likely to be found in the 18-24 age group. In order for our business to succeed and increase profits, it may behoove us as ownersmanagers of this establishment to focus on recruiting from these demographics.

Need Help Automating Your Sales Prospecting Process?

LeadFuze gives you all the data you need to find ideal leads, including full contact information.

Go through a variety of filters to zero in on the leads you want to reach. This is crazy specific, but you could find all the people that match the following: 

  • A company in the Financial Services or Banking industry
  • Who have more than 10 employees
  • That spend money on Adwords
  • Who use Hubspot
  • Who currently have job openings for marketing help
  • With the role of HR Manager
  • That has only been in this role for less than 1 year
Just to give you an idea. 😀

Probing Questions Definition

What is a probing question? A probing question is a series of questions that sales representatives ask prospects to gather more information on an idea. This way, the salesman can create a better understanding about what they are selling.

Probing questions will get you to the heart of your prospect’s problem and give them a better understanding of how your solution can help.

Four Types of Questions

Interviews and official business situations have four major types of questions, these are:

  • Open-ended questions.
  • Specific questions.
  • Motivation questions.
  • Unconventional questions.

Open-ended questions

This type of question doesn’t require a specific answer. Answers vary because the probing open ended questions often lead to an in-depth explanation or summation. The prospect is given space and time to tell their story, which they may not have been able to do otherwise.

To make sure that your prospect is on the same page, you need to ask them open-ended questions. For example: “What are some of the obstacles preventing you from making a purchase?”

What do you hope to accomplish with your business?

This question gives the prospect a chance to share their work history, why they left their last job and what motivates them.

Loaded questions

These types of questions are designed to make the client go in depth about a particular topic. The goal is for them to provide concrete and accurate details.

The questions used during probing should be specific and ask for more detail about the prospects ambitions.

What options have you tried?

Prospects are asked to provide details about any projects they have attempted without success and the techniques that did not work.

Closed-ended questions

One way to help measure a potential customer’s interest is by asking probing questions. The goal of these inquiries are usually either yes, no or short phrases that will reveal factual data about the person you’re speaking with.

Closed-ended questions are typically yes or no, multiple choice, truefalse and in some cases numerical.

  • Do you have a budget?
  • Have you found that this problem is taking away from other aspects of your business?

When I first began hiring salespeople, my instinct was to test pay and commission structure because it seemed like a high base salary combined with lucrative commissions would be enough motivation. However, people are not just motivated by money.

Recall and process questions

If you’re interviewing someone, be sure to ask them about their past experience and what they learned from it. A recall question asks the other person for a specific fact that happened in the past while process questions trigger deep thought or analysis of said fact.

Here are some questions to ask yourself when recalling an event or process:1. What were you doing? 2. Who was there with you? 3. Where did the incident happen and what happened before it started happening (i,e., “The computer screen went blank”)

  • How do you keep track of your contacts?
  • What are the three things you want to come out of this?

Best Probing Questions List

What is an example of a probing question? These are the 30 probing questions examples that have been proven to work in probing in sales. Examples of open probe sales questions are included.

1. How did you hear about our company?

Sales reps can use this probing questions for sales to see how well their company is doing with marketing and branding.

2. How can we help?

An open-ended question is one that asks the prospect to tell you more about their challenges and how your product or service can help.

3. Could you please elaborate?

A common probing questions to ask that sales reps use is the prospect that question about what they’re looking for. This can help them figure out whether or not their product is something that would be beneficial and ultimately solve any problems.

4. When did the situation begin?

Sales reps use this question to find out what the customer has been experiencing and how long they have had these symptoms.

5. Has something like this ever happened before?

This is a common question for sales reps to ask because it helps them find out how bad the problem really is and what they can do about it.

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

The prospects responses to the salesperson can help guide them in their approach. This is considered as one of the probing questions customer service examples.

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

Sales reps should be able to give examples of the customers problem and figure out what solutions would work best for them.

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

This question opens up the conversation to discuss what is most important for prospects, which encourages them to think critically about their expectations and needs.

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

The skills needed to probe are important because it is an effective way of learning about the clients needs and expectations. It also helps set a strategy for what you want them to do during your time together.

10. How long have you been thinking about this?

Have you been trying to solve this problem for a long time? Can you remember when the problem started and how long ago it was that you decided to take action on it?

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

When you have a tech issue, how much time is wasted on trying to find solutions? How does it affect the company’s productivity and workers’ morale?

12. How did this problem begin?

When did you first notice that things werent going as planned? What were the signs and when did it become clear to you that this problem needed a solution?

13. Why isnt your current product/service not working for you?

What is your greatest concern with the productservice you are using?

14. How severe is the problem?

What are the consequences of your ineffective system? Is it affecting your workforce or company budget in any way? How long have you been looking for a solution to this problem?

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

This is a great question to ask because it allows the customer to reflect on their purchase and talk about any issues they may have.

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

The client has been an important factor in the situation. Have they made any attempts to find solutions? Are they part of the problem?

17. What is your strategy to fix this issue?

When a salesperson asks this question, they are trying to find out what solution the client is interested in. They can then work together on coming up with an adequate remedy.

18. Do your competitors face the same challenge?

When I was interviewing my first salespeople, the issue of pay and commission structure came up. It turned out that this wasnt just a problem with our company; it seemed to be an industry-wide trend.

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 companys brand and image?

24. How does the problem affect your potential customers?

Does your sales cycle take longer? Do you have a more difficult time finding prospects and qualifying them into potential customers?

25. Have I missed anything?

The sales rep will ask the customer to go through their pain points in detail, which allows them to provide a more complete 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 Effective Tips On Asking Sales Probing Questions

As we have learned from ILPA, you need to know that the prospect is open for questions. This will make sure what you are saying about your productservice matches up with their needs and wants.

How to probe in customer service? Asking probing questions, which are designed to build rapport and find a solution together with the prospect can help both parties.

Questions are an excellent way to create cooperation between sales reps and prospects, as well as improve the efficacy of a strategy.

Sales reps always know to ask questions, but they dont seem to have a strategy for how these questions should be asked.

When a salesperson makes their first call, they should always start by asking broad questions. When it comes to closing the sale, you need to make sure that your customer is ablewilling to answer open-ended questions because this will allow them time for self reflection and contemplation.

There are some questions that salespeople should ask their prospects and customers, but they need to know how to do it in a way that will get them the best results. It is important for sales people to keep these guidelines in mind when asking probing questions.

1) Steer clear of the word or

We want people to tell us what they need, not just answer yes or no. To do that we have to understand the power of or.

What is the best way to ask questions in order to get a better answer?

What are some of the most common obstacles that you have encountered in your department when it comes to getting projects completed?


I am not sure if the biggest challenge for your department is getting projects out of the door or keeping them on track.

When you are asking questions, the first question is likely to give a descriptive answer with lots of powerful data points. The second question will probably only have one word and not much else. When it comes to gathering information, language can be incredibly helpful.

Prospects are more willing to listen and share information when they feel that you care about them. This is a good opportunity for building rapport with prospects who will be much more open in sharing their needs.

2) Always (ALWAYS) Start with Your Prospects Role

When you are interviewing, it is important to have a list of questions in order. This will give the interviewer more structure and make them less likely to get off track.

The first thing you should do when interviewing is to ask the candidate about their work history and then probe into what they like or dislike about that position. You can also use these questions as a way of learning more information.

1) What are your main responsibilities? I see that you have the title of ____, but just because it is on LinkedIn does not mean that this is all you do.

I’m sorry, I don’t know what you mean.

3) I ask this question broadlywhat are you trying to accomplish as a team? What major initiatives does the company have planned for the year ahead?

4) How is your team measured?

I am going to need you and your team’s help in hitting these goals.

If you want to know what the consequences are for either paying your employees more or less, then

7) What are some of the biggest challenges you face in your job?

One of the most important questions to ask in a sales process is “What do you like about your job?” It gives insight into what they care about and can also give additional responsibilities that are not apparent.

It is now possible to collect all of this data and use it as a tool for your sales pitch. You can tailor the message so that you appeal on an emotional level.

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

It is important to take the time and get a sense of how their team operates. Every business has its own set of quirks that cannot be gleaned from just looking at public information on LinkedIn.

It is important to know who you are talking with and what their role in the company might be. This will give you a better idea of how much they care about your solution, as well as who may have final say or some type of committee vote.

LinkedIn is not the only way to get information about a prospect. Other channels include:

  • Their company website
  • The company’s mission statement is to provide reliable and convenient service for all of our customers.
  • The company had a lot of success on social media.
  • Current customers
  • Read some of the blogs and articles that your prospect is reading or writing.
  • Researching your competitors helps you to learn what areas they are strong in and which ones need improvement.

4) Understand Your Prospects End Goal

The first step to a successful sales call is figuring out what the prospect wants. The most effective way of doing this is by asking probing questions that relate directly to their needs and goals.

As a business owner, you need to know what your customer’s motivation is for buying. You can use this information as ammunition when discussing why the solution they are proposing will not work because it does not meet their needs.

Prospects often use excuses like We dont have the budget, or “Not good timing.” Once you understand their business goals and challenges, these are just obstacles that can be overcome.

Try something like this:

I have found that a lot of people are just not motivated by the prospect of earning more money. It is important to provide incentives other than pay, like flexible work hours or bonuses for success.

Utilize This Data to Challenge Your Customer

There are nuances to the questions you ask based on what youre selling. For example, if I was trying to sell accounting services for individuals or businesses, my initial questioning would be different.

If you always start with the above fundamental questions, your sales pitch will be more compelling and make it easier for prospects to take action now. 

Need Help Automating Your Sales Prospecting Process?

LeadFuze gives you all the data you need to find ideal leads, including full contact information.

Go through a variety of filters to zero in on the leads you want to reach. This is crazy specific, but you could find all the people that match the following: 

  • A company in the Financial Services or Banking industry
  • Who have more than 10 employees
  • That spend money on Adwords
  • Who use Hubspot
  • Who currently have job openings for marketing help
  • With the role of HR Manager
  • That has only been in this role for less than 1 year
Just to give you an idea. 😀
Editors Note:

Want to help contribute to future articles? Have data-backed and tactical advice to share? I’d love to hear from you!

We have over 60,000 monthly readers that would love to see it! Contact us and let's discuss your ideas!

Justin McGill
About Author: Justin McGill
This post was written by Content at Scale, a solution that uses AI + a team of optimization specialists to publish hundreds of high quality, SEO optimized content straight to your blog. It’s the first and only solution that allows you to truly scale content marketing.