9 Clarifying Questions To Ask Your Prospects

9 Clarifying Questions To Ask Your Prospects

Most of being an effective sales rep comes down to effective listening and asking good questions.

Questions get us to the heart of a prospect’s problem so that we can formulate the perfect solution for them.

But not all questions are the same.

Some are designed to gather info, others frame out hypotheticals or paint a vision of the future state, or uncover objections. Asking the right ones is an important skill, and reps need to be coached to do it well.

Today we’re digging into one key piece: clarifying questions – questions that reiterate what you’re heard and give you the opportunity to dig deeper – along with 9 examples and when to use them.

What is a clarifying question?

A clarifying question is a question you use to confirm what the prospect just told you, and get a better understanding of the problem. Clarifying questions help ensure you’re coming to the right conclusion after the prospect has given you a lot of input or said something unexpected.

Clarifying questions are generally closed-ended since you are confirming past answers, not looking for new ones.

But be careful: a clarifying question shouldn’t express an opinion or bias. It should be a simple request for more information, and it should stick close to the topic at hand.

Here’s an example. Suppose a prospect tells you their billing process takes three days.

  • A good clarifying question: Why does it take three days?
  • A bad clarifying question that expresses an opinion: Don’t you suppose that’s too long?

Clarifying questions help us enhance our understanding, frame problems, and generate solutions.

Now let’s run through a few clarifying questions that should be a part of your arsenal. I’ll also mention when to use them and why they work.

1. What resources were used for the project?

Ask this when you want to understand all the factors involved in a particular issue.

Why it works

It works because it gives you a better understanding of the total landscape of your deal, and helps you understand who and what is going to be involved.

2. What criteria did you use to evaluate [prospect problem]…?

Ask this when you want to know what parameters the prospect used to analyse a problem.

Why it works

This question uncovers how the prospect arrived at a particular conclusion they made. It will help you trace their footsteps, and it can potentially reveal a misunderstanding of the problem by the prospect, or give you an opening where your solutions fits.

3. What’s another way you might approach [the problem]…?

Ask this when you want to know if there are one or more approaches to a particular issue other than the one the prospect narrated to you.

Why it works

This is useful to understand all the paths a prospect might take to address a particular problem or to uncover a new path that they haven’t thought about. Oftentimes, you can use this to clarify a potential solution that your product solves for.

man asking client questions

4. [summary of conversation]: Did I paraphrase what you said correctly?

Ask this when you summarize what the prospect has said back to them.

Why it works

Summarizing what a prospect has said helps you make sure you’ve understood them correctly. The prospect will usually narrate their issues in a free-flowing manner without necessarily putting the information in any order. This is not intentional, it’s just a natural way of talking. As the salesperson, it’s your job to distill the important points and neatly arrange them for both you and the prospect to consider. This question gives the prospect a chance to confirm if what you’ve distilled is correct and indeed covers all of the important points. This also lays the positioning groundwork for your solution.

5. Did I hear you say…?

Ask this if you pick up on a term or pain point that your product directly addresses.

Why it works

In the course of questioning the prospect, as they reveal more information they may hit on a term or pain point that is a unique selling proposition of your product / service. This question not only lets you confirm the pain, but is also a nice segue into the conversation you want to have.

6. When you said …  can you tell me the specifics?

Ask this when you want to understand the details of something the prospect said.

Why it works

The prospect may or may not be an expert in the domain in which your product / service is in. For example, suppose you’re selling cybersecurity to a coffee shop owner who wants to provide free Wi-Fi for their patrons. 

They don’t know about Wi-Fi, they know about coffee. They won’t know all the terms and technicalities of cybersecurity – but they will know that their customers are complaining about viruses.

In other words, they may explain the problem in layman terms that don’t really get you closer to the root cause, so you need to dig for specifics and make sure there’s a shared understanding of the problem.

asking questions on video call

7. Can you say more about that?

Ask this when you pick up on something and you want the conversation to go more in that direction so that they reveal more about that topic.

Why it works

This question gets the prospect to go into more detail about a particular point they touched on. It can also be used to invite them to elaborate on something they had previously brushed over, and get them thinking more about their issue.

8. Can you give me an example of ... so I can be sure I understand?

Ask this when you want a specific example / instance of something the prospect is talking about.

Why it works

This question moves the conversation from a high-level, abstract problem to a very real one for the prospect, and gives you insight into the opportunity cost of them not purchasing your solution. 

For example, say you sell payroll software. A prospect might take a call with you because “payroll sucks”. But if you can clarify around that, you might learn that they’re often paying their employees late, leading to a lot of employee frustration. In fact, two people have quit so far this year because they were so upset about payroll being missed. 

Now, you have a much better sense of the problem, and can frame your solution around solving it – fix your payroll, and reduce employee turnover.

9. Is this your biggest problem? Why?

Ask this when you want to understand if what they are talking about is their main pain point.

Why it works

The prospect might narrate a lot of issues, and you want to know the biggest one. Sometimes it’s best to just come right out and ask. It’s also worth digging into why – is it a personal annoyance, or expensive for the business, or part of their job success / compensation? Is it important to the CEO? Learning why will help you clarify how to position yourself.

woman asking client questions


We use clarifying questions all the time in daily exchanges. “I beg your pardon?” “Is that so?” “Can I help you?” It’s nothing new to us.

When it comes to sales, however, the only trick is to ask the right question at the right time. That’s one of the main reasons that sales coaching involves practicing asking questions a lot.

When discovering more about the prospect, you are on a mission to get to the root of their problem. Questions should therefore always be explorative, and never suggestive.

I leave you with a few quick guidelines on using clarifying questions.

  • Don’t shy away from admitting if you are unsure about what the speaker means.
  • Ask for repetition when you need it.
  • Relay your understanding of what the buyer has said, and check if that’s really what they said.
  • Ask for specific examples.
  • Use open, non-directive questions.
  • Always be prepared to be corrected.

Happy selling!