Sales / Sales Process

4 ways to improve delivery of probing sales questions

Sujan Patel

Updated: Dec 19, 2023 · 7 min read

Toolkit for download in this article

probing sales questions

If you’re in any kind of sales role, you’ve probably heard that you’re supposed to be using probing questions in your sales conversations. But what if—like many new or relatively inexperienced sales people—you’ve tried using them, but haven’t seen good results?

Often, it isn’t the questions that are the problem. If they aren’t delivered appropriately, probing questions can feel intrusive or even disrespectful. That doesn’t mean you should abandon probing questions. It means you need to improve the way you deliver them.

Here are four strategies for doing so:

1. Treat prospects like people

Imagine sitting down with a new prospect—someone you’ve never met—and asking them to share their deepest, darkest secrets or their most embarrassing memories. They’d probably look at you like you’ve got two heads—and rightfully so.

Most of us understand that we have to build rapport in friendships and other relationships before getting into such sensitive subjects. But for some reason, that same sensitivity often flies out the window when it comes to sales conversations. Rather than recognize and respect the need for relationship building, we drop in with highly personal questions and expect our prospects to spill out their deepest needs.

Preventing this from happening requires that you take a step back and ensure you’re treating your prospects like people. That sounds overly simplistic, but when you’re in the middle of a major cold outreach push, it can be easy to forget the humanity of each new prospect on your spreadsheet or in your lead list.

A few tips for ensuring you keep the appropriate balance include:

  • Invest in building rapport. Ask the easy questions first. Engage in the small talk we all love to hate. Even if all you’re trying to do is qualify a prospect for further conversations, demonstrating interest in who they are and how they’re doing will go a long way toward helping them respond positively to your questions.

  • Practice active listening. Not only will being a more active listener help you get the information you need from the sales conversation, it’ll help you pick up on more subtle signs of discomfort that suggest you’re pushing too hard.

  • Be personable in your approach. Nothing makes people feel more like a number than a set of rote questions delivered with a completely flat affect. Instead, be energetic and enthusiastic. Treat your outreach as a back-and-forth conversation, rather than a dry Q&A session.

2. Discover root of problems

Knowing how prospects will benefit from your solution is the key to delivering a personalized, highly effective pitch. But most prospects aren’t going to connect the dots for you—even if you take the time to forge a relationship. In fact, they may not even know exactly what their pain points are or what kind of difference your product or service will make if you don’t help them isolate and understand their underlying feelings.

Asking probing questions can help you get to the root of your prospects’ problems, but by asking them, you also capture valuable information that can help improve your delivery of further questions.

For example, imagine you’ve asked your prospect, “How important is it for you to solve this problem soon?” If the prospect reveals that they’re dealing with a high-priority issue, that should affect the probing sales questions you follow up with and the way you deliver them. Conversely, if you discover that the problem you identified isn’t having much impact on them, that’s a signal that you need to move forward with a different line of questions.

To be able to respond quickly in the moment, it’s a good idea to brainstorm a list of different probing questions you could ask and to add to it whenever you use a new question in a sales discovery call. As your inventory of questions grows, you’ll be much better prepared to deliver the right question at the right moment.

3. Avoid misunderstandings

Having a strong list of probing sales questions doesn’t guarantee a flawless delivery. Has this ever happened to you? You ask a prospect one of the probing sales questions on your list, and they immediately get defensive or give you a completely different answer than you were anticipating.

The Ladder of Influence model can be helpful in understanding why these disconnects occur.


The Ladder of Influence model comes from the book, Overcoming Organizational Defenses: Facilitating Organizational Learning, and it underscores the idea that what actually happens and what we take away from a situation can be very different.

At the bottom of the ladder are reality and facts. But on top of them, you and your prospects are layering on your own interpretations of reality, assumptions, and beliefs—all of which contribute to the actions taken as a result of an exchange.

Dealing with sensitive conversations around pain points and needs further increases the potential for wires to be crossed or for important insight to be lost in translation. Probing sales questions give us the opportunity to seek clarification—especially when the consequences of misunderstanding someone can be so significant.

Use the Ladder of Influence model in your sales conversations whenever you suspect that a miscommunication has occurred or if you get the sense that either you or your prospect has jumped to conclusions. Work with your prospect to peel back the unconscious impact beliefs, assumptions, and misinterpretations they may be having by trying to get back to facts upon which you can both agree. Once you’ve reestablished this baseline understanding, you can return to your probing sales questions.

4. Practice your delivery

Finally, practice doesn’t make perfect—especially if you practice poorly. Instead, practice makes permanent. The way you practice your delivery is the way you’ll execute it in a live sales setting, so make sure you’re practicing the exact experience you want to create for your prospects.

As you practice, try to imagine what your prospect is thinking or feeling? What are they worried about? What priorities are on the top of their to-do list? The more you can envision yourself as your prospect, the better position you’ll be in to understand and empathize with their decision-making process.

Final thoughts

Probing questions aren’t miracle workers. They’re just one tool in your toolbox. And just as there are right and wrong ways to use hammers, screwdrivers, pliers, and other physical tools, there are good and bad ways to deliver probing sales questions.

So if you haven’t seen good results with them up to this point, don’t give up just yet. Instead, give the four strategies noted above a try. When applied thoughtfully and consistently, they should have a major impact on the results you get from using probing questions in your sales conversations.

About the author

Sujan Patel is a partner at Ramp Ventures and co-founder of Mailshake. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.

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