Contact SalesStart Free Trial
Learn more about:

How to Ask Probing Questions When Making a Sale

How to Ask Probing Questions When Making a Sale
Casey O'Connor
Casey O'Connor

Casey O'Connor

10 min read0 reads
Sales Prospecting 

Contents

  1. What Is a Probing Question?
  2. 6 Types of Probing Questions + Examples
  3. How to Avoid “Leading” Questions
  4. Tips for Great Probing Questions

High sales performance relies on effective questioning from sales reps. Every stage of the sales process, from prospecting to negotiation, requires a salesperson to ask questions.

The most successful sales professionals understand not only when to ask questions, but how. Surface-level questions will only drive a meeting so far forward; reps need to ask probing questions to get to the heart of what a prospect needs.

Mastering the act of asking skillfully-phrased probing questions can:

  • Grow your pipeline
  • Shorten your sales cycle
  • Improve customer success rates

In this article, we’ll go over everything you need to know about thought-provoking probing questions, including the six standard types, real-world examples, and how to avoid making your client feel pressured when you ask them.

Here’s what we’ll cover:

What Is a Probing Question?

A probing question is one that’s designed to provoke deep thought from a prospect on a particular topic. Probing questions are presented with the intention of encouraging the prospect to get to the heart of what they really need from your product.

Probing questions can be leveraged throughout every stage of the sales pipeline.

probing questions: sales pipeline

When delivered correctly, great probing sales questions can help a prospect build trust with the seller and prompt them to offer candid information about their pain points.

The right series of questions can enable sellers to collect the kind of information that ultimately helps the sales rep close valuable, mutually-beneficial deals.

Becoming effective at different probing techniques can take some practice. The first aspect to understand is that probing questions are always open-ended questions.

probing questions: open-ended questions

To be clear, though, probing questions are more than just “open-ended.” In fact, they’re usually quite a bit deeper and more thought-provoking than most discovery questions.

Think of it this way: Discovery questions help sales reps discover the issue. Probing questions help them develop a strategy for positioning your product as the solution.

Effective Probing Questioning Techniques Will:

Grow Your Pipeline

Sales reps and SDRs can learn how to leverage probing questions to quickly qualify leads. They can then offer the marketing team feedback about the characteristics of best-fit clients, enabling them to optimize their efforts for attracting more highly-qualified leads. 

Shorten the Sales Cycle

Probing questions can be highly effective at every stage of the sales process. Reps can save valuable time in everything from prospecting to overcoming objections when they learn to ask the right questions at the right time.

Improve Customer Success

The better a sales rep becomes at asking deep questions, the more likely they are to deliver the exact value each prospect genuinely needs. Probing questions throughout the sales process can help account executives and customer success teams support the customer base in ways uniquely meaningful to them.

Ultimately, probing questions are so powerful because they bring meaningful personalization to the sales process. Don’t underestimate the impact of this — 44% of clients report they’re likely to take their business elsewhere in case of subpar personalization efforts.

user-groupKnow what's workingUncover what's resonating with prospects with robust reporting capabilities

6 Types of Probing Questions + Examples

There are six primary types of effective probing questions, each with their own nuances, specific points, and optimal timing. 

1. Rapport-Building

Some probing questions are designed to build rapport and trust with prospects. Skilled salespeople can use a buyer’s personality type to help them decide which kinds of questions will be most effective. 

probing questions: rapport-building

These probing questions aren’t meant to be idle small talk; use this time wisely, even if you’re not talking about deal terms yet. Building rapport with good questions creates a critical foundation for a successful sale — over 80% of buyers report that trust is a deal-maker or deal-breaker in their buying decision.

Examples of rapport-building probing questions include:

  • I see you live in ___________. Have you ever been to {local landmark}? I came across it in an article and it stuck with me for some reason.
  • Did you read that {relevant article in prospect’s industry}? What did you think of that?
  • Have you traveled recently for work or leisure?

2. Problem-Solving

Some of the most popular probing questions are the ones designed to uncover the exact nature of the prospect’s problem. Sales reps ask these when they want to know the core of the prospect’s deepest pains and motivations.

Sales reps can feel comfortable asking problem-solving questions relatively early in the sales process, usually right after some rapport is built. 

Examples of problem-solving probing questions include:

  • How much is this problem costing the company? In time? In dollars?
  • How would you describe the problem you’re trying to solve? Why haven’t you solved it yet?
  • What worries you most about the current problem?

3. Solution Questions

Solution-oriented probing questions should help steer the prospect into vocalizing their ideal outcome to the problem. 

If prospects can express what exactly they yearn for in a solution, sellers can use that feedback to position their own product as the one best-suited to their specific needs.

This line of questioning should be reserved until after the prospect and seller have a mutual understanding of the prospect’s problem.

Examples of solution-oriented probing questions include:

  • What does the ideal solution look like to you?
  • Beyond product features, what are the brand qualities you need from a provider?
  • What are your must-haves and nice-to-haves in a solution?

4. Buying Process

Probing questions about the buying process help sales reps understand how to navigate the sales process in the way that delivers the most value to that particular prospect. 

These are best received after the problem and solution have both been discussed. 

Examples of probing questions about the buying process include:

  • Can you tell me more about your decision-making process? Who is involved? Is there a timeline?
  • What additional information do you need to feel ready to make a purchase?
  • Have you ruled out other providers for this solution? Why?

5. Budget Questions

Like it or not, all sales conversations must include details about the prospect’s budget. Probing questions around this topic can help sales professionals understand where the prospect places the highest value, and position themself as the best way to deliver it. 

Probing questions around the budget can also help sales reps work with prospects to find additional sources of funding. 

Questions about the budget can be asked at around the same time you ask about the buying process. 

Examples of budgetary probing questions include:

  • Do you have a budget range in mind?
  • What will happen if your available budget doesn’t cover the cost of your must-haves?
  • Are there opportunities for additional funding?

6. Deep Probing

Deep probing questions are classified as any other open question that requires critical thinking.

These “miscellaneous” types can technically be asked any time after rapport is established, but take that rule with a grain of thought. Some probing questions are more sensitive than others, so use your judgment about appropriate delivery timing.

Examples of deep probing questions include:

  • Can you tell me more about that?
  • How do you feel about that?
  • Can you be more specific?

Remember that the intention of asking these types of questions is to get the prospect to “open up” and share some of their deepest frustrations. Although there are six “types” of probing questions, don’t treat them as cookie-cutter content.

Any hint of a script, or attempt to make your question seem like a certain “type” will likely make the buyer put their guard up.

chart-barReach more prospectsAutomated campaigns with email, calls, and social touches

How to Avoid “Leading” Questions

Be careful not to confuse “probing questions” with “leading” ones. While probing questions aim to get to the heart of what a prospect truly thinks or feels, a leading question attempts to sway a prospect’s answer through the way it’s present.

Leading questions are biased and are designed to “lead” the responder toward answering in line with a particular viewpoint, usually that of the questioner.

Probing questions, on the other hand, attempt to guide the prospect toward reporting authentically on their own viewpoints.

Tips for Great Probing Questions

Remember that becoming skilled at asking probing questions takes time and practice. Keep the following tips in mind as you master this skill.

Active Listening

Your body language and verbal cues can go a long way in helping your prospect feel more comfortable in opening up to your questions. Try using active listening skills to help your prospects feel more trusting toward you.

probing questions: active listening

It’s particularly important for sales reps to be attuned to and reflect any feelings that a prospect displays.

Practice Your Timing

Sometimes, the timing of the question is as important as the content itself. Try to classify your most common probing questions by type according to the outline above, and ask them within their recommended timeframe for best results.

Get Rid of Your Bias 

Remember — stay away from leading questions. It’s natural for you to think that your solution is the best on the market, but avoid pushing your prospect into prematurely adopting the same point of view. Make sure the questions generate the prospect’s own opinion, not ask them to reiterate your own.

Have you practiced using probing questions? What was the outcome? They can feel challenging and even uncomfortable at first, but with time and practice, they can become second nature.

Get expert sales tips straight to your inbox to win more deals

Yesware is an all-in-one toolkit for sales professionals and sales teams. Try our Outlook or Gmail add-on for free!

Hit your number every month

Get Yesware for free

Works on Outlook or Gmail (+ many more integrations)

Related Articles

How to Ask Probing Questions When Making a Sale
Casey O'Connor

Casey O'Connor

How to Build a Sales Lead Funnel
Casey O'Connor

Casey O'Connor

How to Create a Sales Persona Template
Casey O'Connor

Casey O'Connor

Sales, deal management, and communication tips for your inbox