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Sales - 9 min READ

The psychology behind asking effective probing questions

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Copper Staff

Contributors from members of the Copper team

If you think therapists, journalists and detectives are the only ones who can benefit from asking probing questions, think again.

As a sales rep, you too can approach your prospects with a curious mind, using the power of intelligent questioning to uncover their most pressing pains and frustrations by asking a probing sales question.

In fact, the very first step in the popular sales framework, CHAMP, is to understand the prospect’s challenges. This approach allows you to identify opportunities as well as demonstrate exactly how your product or service will help them solve their unique challenges, which can include sales probing questions that a sales rep can ask.

Unfortunately, many salespeople aren’t asking the right questions—or, rather, they’re asking the right questions but in the wrong way (like asking yes-no questions versus probing questions).

Understanding the principles behind effective questioning and why it works can help bridge the gap between each salesperson and prospect. This can be learned if salespeople study probing questions examples in sales.

This piece will touch on different approaches to asking probing questions, and important tips to keep in mind. However, before we dig into that, let’s take a trip down memory lane to uncover the origin of probing questions.

Do as the Greeks do

The method of asking effective probing questions can be traced back to Greek philosopher Socrates.

Socrates believed that disciplined questioning encouraged his students to dissect complex ideas, uncover the truth, and challenge assumptions, among other things. He called this approach—aptly—Socratic questioning.

“Only by understanding the root of the prospect’s pain can you provide them with a solution.” (Nah, he didn’t say that, but he definitely would have about sales probing questions.)

Socratic questioning differs from standard questioning in that it is “systematic, disciplined, deep and usually focuses on fundamental concepts, principles, theories, issues or problems.” In other words, Socratic questioning was developed to effectively and efficiently get to the very core of a problem.

In sales, this is essential for a salesperson to learn. Not only because (as mentioned) it uncovers sales opportunities, but also because it does so in a timely way. And every minute you spend with an existing prospect is one more minute you aren’t spending with a new prospect.

4 tips for asking effective probing questions

There’s more to effective probing questions than just the questions themselves. In fact, how you ask them, how well you listen to their answers, and how you respond to them will all contribute to the overall effectiveness.

The following tips will help you get more from your questions, maximizing the precious time you have with your prospects.

1. Check your bias

In order to get to the truth of your client’s struggle, you need to make sure you’re not projecting any of your own biases or assumptions onto them. Sure, you may have worked with a similar client just a few months prior, but that doesn’t mean they’re experiencing the same challenges.

Each and every client is unique, so it’s important to avoid making assumptions, since that will position you at a disadvantage. You’ll either alienate the client early on, making them feel like you’re not listening, or you’ll present them with solutions that don’t quite fit, making it harder to land the sale.

(That said, there is a place for leveraging bias—cognitive bias specifically—when it comes to sales and marketing. But that’s a different post for a different day.)

2. Practice active listening

In the consultative selling model, asking probing questions and practicing active listening are two of the five main principles. And in fact, you can’t truly benefit from one without the other.

If you’re taking time out of your prospect’s day (and your day for that matter) to dig into their pain points and challenges, practicing active listening will do two key things:

  1. Show your client you’re invested and committed to helping them
  2. Ensure you fully understand their perspective, free of any ambiguity or uncertainty

To ensure you’re practicing active listening, repeat your prospect’s answers back to them in your own words. (Of course, you don’t want to do this every time—that would get awkward. Instead, use other cues to indicate you’re listening—such as nodding—and repeat back answers that are particularly complex to ensure you’re both on the same page.)

And make sure you take detailed notes—this helps you better retain their answers, and gives you (and your team) something to refer back to when questions arise or another teammate needs to step in and assist. Active listening in also incredibly value later in the customer lifecycle when gathering customer feedback.

3. Avoid asking “Why”...unless it’s a clarifying question

When initiating sales conversations, think of yourself as a journalist asking a probing question — consider these 'discovery questions' — as opposed to a police officer. This approach will ensure you're adopting an investigative attitude, rather than an interrogative one.

One trick to keep in mind is to avoid using “why” in your questioning. In an Inc. piece, a former FBI negotiator reported that “why” questions make people feel defensive, because they’re often interpreted as accusations.

That said, there are some instances where “why” questions are appropriate—like when you’re following up with a clarifying question.

For example, say your prospect tells you they never use a certain feature of their current solution. It would be appropriate for you to ask them why at this point. (“How come?” would work too.) Perhaps it doesn’t integrate with another tool they use, or they simply don’t understand the benefit it provides. This is key information that could help differentiate your product or service from your competitors’.

4. Use yes-no questions to your advantage

Probing questions are generally open-ended questions; however, sometimes you need to ask yes-no questions to get down to business.

Here’s a thought, though: instead of asking questions that push for a positive response, consider asking questions that encourage the prospect to say, “No.”

According to the same former FBI agent, we’re “yes battered,” meaning we’re constantly being pressured to say yes to some offer or another. As such, people want to exercise their right to say no, so why not give them the opportunity?

Rather than asking a prospect “Do you have a few minutes to chat?” consider rewording the question to “Is now a bad time to talk?” He says the same logic can be applied to email, so give it a try and see if your prospects’ responses change.

Of course, this is anecdotal, but any way to reduce friction along the buyer’s journey, through the use of a sales question, is worth a try.

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Try these probing questions to dig deep

Asking probing questions means going beyond surface level and getting to the heart of a problem.

In order to do this, you might need to branch out from your usual approach and try something new when bringing up a sales question. Here are a few examples of qualifying questions:

Establish their origin story

Discovering why your prospect has decided to look for a solution now will tell you a lot about their motivations.

Perhaps they’re new in their role, and they’re eager to make big shifts in the department they now manage.

Maybe the contract with their current solution is expiring soon, and they can no longer justify the cost and are looking for a more affordable solution.

Or maybe they’ve been talking to an industry peer and have heard great things about your service and solution.

Whatever the case, you’re sure to learn a ton by identifying the straw (or straws) that broke the proverbial camel’s back and pushed them to start actively looking for an alternative solution.

Some probing questions that will help you establish your client’s origin story include:

  • Tell me about your role. I took a peek at your Linkedin profile, but I want to hear from you what you’re responsible for.
  • What are you trying to accomplish as a team this year?
  • How did you hear about us?
  • What made you get in touch?
  • What made you say yes to this meeting?
  • What led you to start looking for a solution now?
  • Tell me about your current solution and what’s not working for you.
  • What other companies are you evaluating?

Discover the root of their pain point

When you first start talking to a prospect, they might already have a running list of problems they need solving. This is a great; however, digging deeper with qualifying questions might uncover a single problem that’s creating a domino effect in their lives.

For example, let’s say your prospect owns a bakery. They’ve come to you because they’re unhappy with their current point of sale system and yours was the first one that came up when they did a Google search.

They complain that their current system is too complicated and their staff can never find what they need. They say it takes too long to cash out at the end of the day, and that their end-of-month reports always seem off.

If you were to take your prospect’s complaints at face value, you might believe their problems are related to their current tool’s lack of intuitiveness. However, upon further investigation, you might discover that they never received proper setup and implementation training. The system itself is not all that complicated; however, they were never provided with the support necessary to actually understand its value and power.

This is a huge opportunity for you, because your company does offer superb customer support and training. In fact, you even have a case study on hand which details how another bakery was up and running with your product in less than 60 days.

So remember: if you’re just identifying your client’s pain, you’re only doing half your job. Instead, go further to try and identify the original source of their pain. Some questions you might ask to do this include:

  • Tell me about your current process.
  • What’s frustrating about your current process?
  • What does this process look like, and how does it flow in an ideal world?
  • What would provide you with the most relief or value right now?
  • What projects are you currently working on now?
  • What is preventing you from executing on these projects with ease?
  • What would have made your experience with your current solution better?
  • How might your current providers better helped you succeed?
  • Who will use the product/service?

Anticipate potential roadblocks

You can learn a lot about a company’s organizational structure and processes early on if you ask the right probing questions.

These types of questions might not be as important to you in the early stages of the buyer’s journey; however, they’ll help you anticipate possible future roadblocks and enable you to build a plan of action ahead of time, reducing friction down the road.

Some probing questions you might want to ask include:

  • Who typically makes purchase decisions similar to this one?
  • Who else needs to be involved in order to make this a reality?
  • Are there any constraints that might block us from moving forward?
  • What does your budget look like for fixing this problem?
  • Can you tell me about your company’s priorities this quarter/year?
  • Tell me about the other major initiatives folks are working towards in your company.
  • What steps do we need to take to make this happen?

Consistency is key

As a savvy sales professional, you’re probably already asking effective probing questions and not even realizing it.

However, leveraging the power of probing questions with consistency and intention will not only improve your sales conversion rate, but also make you feel like you know your prospects and customers better than ever.

With a few simple tweaks and following the probing questions examples in sales, you can refine your current sales process to collect more complete and in-depth information from your prospects earlier on. Plus, learn how to do it at scale with our on-demand webinar, 5 ways for sales to prospect more effectively.

After all, once you see the positive results you get from implementing effective probing questions with one lead, you’re gonna want to repeat it.

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