50 sales-probing questions to better understand your prospects

Striking up a conversation with a stranger can feel daunting. If you’ve ever stumbled over your words asking for directions or dared to invite someone you like for a coffee, you know the feeling.

For sales reps, especially those new to the game, finding the right questions to ask is half the battle. Enter the probing question—a sales tactic that will help your team seal more deals.

In this article, we’ll explain exactly what a probing question is and share probing question examples that will get even the most tight-lipped prospects to open up.

What is a probing question?

A probing question is an open-ended question that nudges prospects toward revealing more information about their situation. Learning about a prospect’s needs, wants, budgets, and goals keys sales reps to the best tactics to guide their prospects toward buying.

What is the purpose of asking probing questions?

The purpose of a probing question is to learn more about your prospect’s needs so you can better meet them. Probing questions for sales illuminate the best pathway toward a purchase.

Remarkably, 70 percent of purchasing decisions are made to solve a specific problem. Once you learn what challenges your prospects face, you can adjust your sales pitch to best fit their needs. How can you learn? By asking questions, of course!

Probing questions work across all channels. You can deliver probing questions via emailphone call (whether cold calling or following up), or in person.

Types of sales probing questions

Types of sales probing questions, fingers pointed up

Most sales companies use four types of probing questions to start great conversations: open-ended, loaded, close-ended, and recall and process.

Open-ended questions


An open-ended question is a broad question that doesn’t have any specific or short answer. These enable prospects to tell stories about their own situation in detail. Craft open-ended questions that stick to a specific topic, however. You want prospects to talk about their experiences, but only their relevant experiences.

A good example would be, “What are your company goals?”

The individual should focus on sharing their hopes for the business. With a bit of direction, they’re far less likely to wax poetic about the company’s mission or how many different products they sold last quarter.

Closed-ended questions


Closed-ended questions are the opposite of open-ended questions—they usually have specific answers, leaving no room for the prospect to ramble. Often, answers will be short—even just a “yes” or “no.” Use these questions in moderation to collect factual data.

For example, “Is this issue a top priority for your organization?”

Don’t be surprised by a simple “yes.” That’s still useful information. If your product addresses this issue, you know this prospect will want to hear more. If the prospect answers “no,” move on to a less closed question to gain more information about their needs.

Loaded questions


A loaded question is designed to lead the prospect to provide answers about a specific topic, phrased in a way that gives you an advantage. You’re swinging in with a slightly biased question and looking to lead the prospect to a realization that points directly to your solution.

A good example of a loaded question might be, “So how did your previous solution fail to meet your expectations?”

This leads a prospect to expound on the disappointment of a previous solution—positioning your product or service in a better light and reinforcing their need to switch. Loaded questions can be effective, but should be used sparingly as they can come across as manipulative.

Recall and process questions


Recall questions require the prospect to remember important facts about their business. Process questions push a prospect toward deeper critical thinking about systems in place at their organization. Both questions aim to draw more detailed insights out of a prospective client.

Here’s an example of a recall question: “Has your company ever tried CRM software before?”

If you’re selling CRM software, you’re getting the prospect to recall if they’ve tried a similar product before. If they have, share what makes yours superior. Does your product cost less or have a unique value proposition or feature? Know what makes your product the best and share that insight with your prospects when the moment presents itself.

A strong process question is, “How do you hope this product will improve your business?”

Now your prospect is geared to the results they’re hoping for and the positive impact this product will have on their existing systems.


Sales probing questions examples

Sales probing questions examples, person holding book

1. What do you do?

This classic question feels friendly and welcoming when you’re starting to get to know a potential client. It’s also open-ended, inviting the individual to talk about their work situation. This can yield a lot of information about the prospect’s business and their own place within it.

In B2B sales, asking this question can help you establish if this individual has final purchasing power or if that’s someone higher up the chain.

2. What’s your current situation?

While this question may seem vague, asking about a current situation can spark a fantastic sales conversation. Let the prospect open with what’s foremost on their mind. They may take you right to their primary issue, providing the opening you need to share your perfect solution. If this approach doesn’t work, you can always shift to more specific questions.

3. What issues are you looking to address?

Here’s a more specific probing question in which you’re guiding the conversation. Get the prospect to talk about the problems they need help with. Once you have a clear picture, position your product as part of their solution.

4. What are your goals?

Sure, you need to know what frustrates your prospect. But it’s just as important to understand a potential client’s hopes for the future and what they want their company to achieve. Certain prospects are attracted to a product’s positive impact and the opportunities it opens up, rather than just the problems it solves.

5. What brings you here today?

This is another masterful opener. Its flexibility allows the prospect to speak to whatever’s most pressing on their minds, but it also highlights their timing. Why today? Did they try a different solution that failed? Are they heading toward an important business milestone and looking for a boost? You may just end up with a terrific angle for your pitch.

6. Are you considering any other options?

By bringing up the competition, you can suss out what other options are on the table. You need to know who you’re up against so you can speak to what makes your product or service superior.

7. What led you to consider our product?

Get a prospect talking about what initially drew them to your product specifically. Of course this helps your potential client sort through their thought process, but you may also discover what could attract future customers. If one person finds a product attribute appealing, chances are others will, too.

8. Are you familiar with our product?

Discover whether your prospect has done any product research. There’s no need to repeat information that the prospect already knows. Conversely, if they have no idea about your product, begin with a broader sales pitch to introduce them to it.

9. Where is your business located?

If you’re at all familiar with the area in question, take advantage of this opportunity to establish a personal connection. You’ll also likely learn more about the size or type of their local industry.

10. What are your priorities right now?

Is solving this issue the prospect’s priority? How urgent is their need? This question can provide information that can help you work on their timeline and prioritize what feels most pressing for them. Not only will you better meet their needs, but this question can help prospects feel heard.

11. Should we add someone else to this conversation?

Just because the individual you’re talking to doesn’t have personal purchasing power, doesn’t mean the sale is lost. A question like this one opens the door to further conversation with someone who can make the purchase. Plus, if you’ve already gotten your initial contact on board, it’s easier to convince a higher-up.

12. Can we schedule a time to talk again?

Don’t take indecision as a “no.” Your contact may be genuinely on the fence. If they’re not yet ready to buy, set up a time to talk again. Just because now’s not the moment doesn’t mean things won’t change in the future.

13. How did you hear about us?

Take advantage of an opportunity to gain insight into how well your marketing strategies are working. See what channels successfully draw in new leads. It will also illuminate what caught this particular prospect’s attention.

14. What can we do to make you feel comfortable buying?

Sometimes you need to pose a direct question. If you feel like you can’t close the deal and you’re not sure why, it’s not out of line to just ask. People appreciate transparency. They may just tell you how you can support them.

15. Is there anything else I should know?

When a prospect is getting ready to leave, it’s wise to ask this final check-in question. Maybe they forgot to mention a detail that will prove helpful next time you talk.

35 additional probing sales questions

35 additional probing sales questions, notepad

Sales reps can and should ask more specific probing questions. Try out some of these insightful inquiries:

Product-probing questions


  • What’s your ideal outcome for using this solution?
  • What’s the first thing you’ll do with our product?
  • What makes this purchase important to you?
  • What happens if you don’t buy our product as a solution?
  • What features are you most interested in?
  • If this solution works, how will you spend the time you’d save?
  • What makes you excited about a product like this?
  • What concerns do you have about this product?

Financial-probing questions


  • What’s your ideal budget for this purchase?
  • Do you have any wiggle room in the budget?
  • How will you use potential savings?
  • Who has the final say on purchasing in your company?
  • Would you like to hear our rates as compared to similar products?
  • What’s a ballpark amount you’re looking to spend today?
  • How much money has this issue cost you already?


Clarification questions


  • Can you elaborate on that?
  • Can you explain what you mean by that?
  • Have I missed anything?
  • Why is that the case?
  • What’s your next step?
  • Can you be more specific?
  • What’s important to you?
  • Has anything changed since we last talked?

Client-probing questions


  • What’s the timeline for solving this issue?
  • How does decision-making work at your business?
  • Can you tell me about your team?
  • What do you value most?
  • How long have you worked at this company?
  • Can you tell me about your job?
  • Can you tell me about your company’s current strategies?

Action-oriented questions


  • What concerns can we address immediately?
  • Are you interested in seeing how this works?
  • Can we schedule a follow-up conversation?
  • Would you connect me with a higher-up at your company?
  • How would you like to move forward?


Strategies for asking probing questions

Strategies for asking probing questions, two people talking

How you deliver a probing question is just as important as the question itself. Here are some strategies to effectively ask thoughtful questions:


    • Practice active listening. Make the prospect feel heard and use what you learn to cater your sales pitch to their needs. Better-angled sales pitches improve your sales funnel.


    • Search for the root of each prospect’s issue. They may not see their needs in the same way you do. Assure them your product is not just a workable solution, but the best one for their needs.


  • Be clear and approachable. Don’t confuse potential clients or put them on the defensive. If you sense a miscommunication bubbling up, redirect or simplify your sales approach.

Leave a Reply