Improve your Selling skills and get more sales by implementing the art of probing questions.

Improve your Selling skills and get more sales by implementing the art of probing questions.

Salespeople are inundated with many smart tricks and tips to take on board; the spoilt for choice seems to bewilder them. However, one such scheme needs to be perfected no matter how advanced our sales enforcement becomes—the effective questioning skills. Asking questions is critical to high sales performance. With the right set of questions, salespeople can unearth the buyer's deepest secrets and desires that may help them to ease their decision-making process.

Why ask effective probing questions?

If you think therapists, police officers, or journalists are the only professionals who know how to dig out the truth with their superior questioning power, you are wrong. In sales, the first framework is to understand the crux of the prospect's problem. This addresses the underlying opportunities and demonstrates precisely how your product or services can solve their nerve cracking problem. Also, by understanding the principle behind effective questioning, you may bridge the gap between you and your prospect.

Before proceeding with the set of questions, let us ponder the skills required to prepare oneself to become pro at probing questions.

When Thomas Kuhn said, "the answers you get depend on the questions you ask," he was definitely onto something.

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  • Active listening

    Questioning is not a rapid-fire series to pry information and get nothing out of too much information. Precisely it involves active listening as one of the essential skills. Let the prospect talk and do not interrupt them until there is a necessity. This allows prospects to reveal information about their challenges in their own words. It also helps in building relationships as the prospect feels heard. When salespeople develop a habit of "no listening to respond" it makes all things smooth and straightforward for both the sides.

  • Check Your Bias

    Biases mean clouding your client's belief. To get to the pit of your client's issue, you have to refrain from projecting any biases or prejudices towards them. It is obvious the anxiety arises as the prospect raises a similar problem that you counteracted months back, but the same strategy doesn't work every time. After all, you must have heard there is no place for one size fit for all approaches.

  • Know when to ask questions

    Asking powerful questions can strike you a deal, but the problem is when to ask pertinent questions. Suppose a prospect is complaining about a product. In that case, you cannot ask him, "how much is the problem costing you". Here, pacifying the person is more important. Later on you can put forth a question like " what timeline do you require to develop a solution for you"?. Also, when a prospect is being emotional or sharing their anecdotes, do not become very friendly and jump at the opportunity to ask questions. Instead, a few kind words and humble gratitude can work magic there.

  • Right Attitude

    A salesperson with the wrong attitude will always be frowned upon. Instead, a representative who approaches a sales meeting as a conversation to establish trust and uncover buyers' needs is welcomed with open arms.

The art of asking appropriate questions at the right time and having a positive attitude will result in a more productive outcome.

Chalk Walk emphasizes on few essential steps that ensure your journey of probing questions to your prospective client become an easy one

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Establish their origin story

When you discover your prospective client is eager to learn about your product or service, it gives you a chance to peek at their intentions. Perhaps they are willing to make shifts in their service or product, or they are looking for an affordable solution, or maybe your service or product could be the talk of the town; whatever the case, you're sure to learn a lot by probing them further to identify the needle in the haystack.

Be Curious as a bee.

Business executives often jump at the opportunity to pitch their product, but if they can hold their reins a little longer and curb their curiosity. They can discover where the actual pain point is. Without asking more questions, you may address the wrong issue; it is vital to wait till the last question is asked. It is like a key that will open the doors of your fragile hopes.

Discover the root cause

While probing your client, you may have noticed they have a never-ending list of problems rolling down on the floor. You may think this is a fantastic opportunity, but digging deeper, you may unfurl the main problem creating the domino effect.

Ask smart questions

Now you must be wondering how to identify the root cause? The answer lies in asking smart questions. The ability to ask smart questions will help you to understand their point of view and circumstances and the context of the issues they face. However, these insights are difficult to bring forth unless given a thought to them.

Ask Open-ended questions

Are you bothered about how to ask smart questions? Apply the power of open-ended questions. Rephrase your close-ended questions by giving them a more thoughtful approach. Instead of asking, Do you think you need to improve your account management system? Ask What about your current account management system do you think needs any improvements?. The answer may not be readily available to you, but with a series of questions, you can tailor your pitch to match the information you find from these questions, and it is worth a fortune.

Coach the decision

Gone are the days when sales professionals would coax clients into buying their product or service; nowadays, it's a more pragmatic approach. And it is one of the best methods suggested to coach their decision to make the purchase instead of convincing the other customer to buy your product or services.

Elevate conversation to a business level

Open questioning or insightful information doesn't necessarily make your conversation supercharged. But when you uplift your discussion to a business level is where the actual value-based selling comes. By elevating your conversation, you tie your solution to the business results for the company rather than just a simple problem-solution approach.

Anticipate roadblocks

Whoever said "selling is as easy as pie" would be lying because selling is a mixture of potholes laced with apprehensions and anxiety at every turn; therefore, a plan of action in advance will reduce friction down the road.

Refer buyer’s perspective

Every potential buyer has a specific opinion and perspective about their business. Your job as a salesperson is to probe questions that challenge those views and offer a better perspective.


As an astute 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 improve your conversion rate and further cement the relationship between you and your prospective clients. With a simple approach, you can refine your current sales process to collect more complete and in-depth information from your prospects.

And don’t forget ChalkWalk will render full support to scale it more effectively. After all, once you see the positive result you get by implementing probing questions with one lead, you want to repeat it.

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