The philosophy behind strategic questioning is to encourage a dialogue which creates or discovers information rather than just communicating information that is already known. By asking thoughtful questions and considering the answers before moving forward, the thinking is that the conversation can evolve beyond the usual and predictable outcomes.

Great Sales Interactions

I’ve observed my fair share of sales of interactions – in-person, over-the-phone, in group settings, via webinar – you name it. Although there are varying skillsets and various nuances to each type of interaction, one element of effective sales conversations tends to remain consistent and that’s strategic questioning.

Strategic questioning can be viewed as a small piece of the bigger need-based, or consultative selling puzzle. Let me explain what strategic questioning entails, and tell you how to best prepare to execute the practice, and we’ll finish with the undeniable benefits.

First, a little background…

At their core, strategic questions are open questions that inspire movement, reflection, and lend themselves to situations where fresh thinking is needed. I believe that strategic questions enable people, organizations, and networks to move forward and explore new possibilities. It can even be said that they facilitate movement from the world of “you should” into the world of “how could?”

Strategic questions are only part of strategic questioning.

Let’s expand upon those thoughts by recognizing that strategic questioning is actually a two-pronged process – it involves well-planned questions and careful, active listening. Without implementing one or the other the practice becomes far less effective.

The philosophy behind strategic questioning is to encourage a dialogue which creates or discovers information rather than just communicating information that is already known. By asking thoughtful questions and considering the answers before moving forward, the thinking is that the conversation can evolve beyond the usual and predictable outcomes.

What’s the best way to prepare yourself?

Strategic questions require preparation and practice. You understand qualifying questions and the differences between closed-ended and open-ended questions. Strategic questions, however, have to dig deeper – and more so now than ever before. Today’s buyer has access to virtually unlimited amounts of information. It’s important to keep this in mind not only as you prepare your questions, but also during the course of the conversation. If the buyer reveals a deep level of knowledge surrounding your product or service, it’s important to tailor your questions accordingly so that you don’t bore them or lose their interest. By the same token, if you get the vibe that the client has not done their homework, you’ll need to take a more holistic approach to the conversation until you can figure out what solutions you offer that will make the most sense for that particular client.

You will be listening for information that will help identify your client’s needs, position your solution effectively, and show the value of your offering in terms that are relevant and meaningful. In your preparation for sales meetings, you can construct several kinds of strategic questions that:

• Identify information about the current situation or what already exists:

“What aspects of your _____ concern you right now?”
“How has your competitor’s new roll-out affected your sales?”
“Describe a typical day for your technicians in the field.”

• Reveal opinions and attitudes:

“What do you think about…?”
“What are the reasons for…?”

• Uncover values, expectations, and ideals:

“What changes would you like to see in…?”
“If you had the chance to redo _____, what would you do differently?”
“What steps would you like to take to accomplish your goal of ____?”
“What’s most important to you?”

• Consider other perspectives or outcomes:

“What effect do you think ____ is likely to have on _____?”
“How do you think _____ will affect _____?”
“What would happen if…?”

• Define actions:

“What else would you need to consider before implementing this?”
“What additional resources will you need?”

When you construct your questions, be aware of how you phrase the question. Consider the difference between these two questions:

“Why don’t you expand your employee benefits package?”


“What keeps you from expanding your employee benefits package?”

The second phrasing is less negative and will draw a response with more information.

The most important part of asking these questions is listening to the response. You should be listening for key words that clients use. Listen for their expectations. Listen for potential obstacles. Listen for their assumptions. Use what you discover, to ask additional questions that reveal your understanding and move the dialogue toward a sale.

“If you were the client, what questions would you want to be asked?

“If you were the client, what would you need to be convinced of to purchase this product/service?”

Are you “discovering” the idea?”

Imagine the benefits of applying this type of questioning to sales:

How would your sales interactions change if your client were to feel as if he or she were discovering ideas rather than being sold ideas?

How are your client’s perceptions of you as a salesperson likely to change if you ask more questions about their business and deliver less canned presentation?

Are you “discovering” the ideas?

Practicing strategic questioning allows you to position yourself as more of a consultant than a salesperson. You and your client are now on the same side as creators of strategies to improve the client’s business. Moreover, decision makers are more likely to believe in and commit to ideas that they discover themselves as opposed to ideas that come from someone else.

Unfortunately our experiences with education taught us the paradigm that teachers spew out knowledge that students must catch. We transfer that same paradigm to sales interactions where decision-makers tend to expect the salesperson to spew out a sales presentation while they must sit and listen for how it might benefit them.

But by asking strategic questions and actively listening to your client’s response, you and your client create a dialogue where new ideas are synthesized from your client’s existing experience, knowledge, and ideals. You are no longer disseminating information or pushing your vision—instead, your client is discovering their vision with your product/service effectively positioned as a solution.

Don’t get caught up in the Close

What it really comes down to is a renewed sense of curiosity. Don’t be afraid to slow down and ask “why?” Don’t be fearful of taking the conversation somewhere you normally wouldn’t – because your clients will, with or without you. And take time to truly listen to the answer – ask to actually understand. Spend a few minutes getting to know someone. Sales professionals tend to get so caught up in the close, they forget they are dealing with real people on the other end of the phone, inside the computer, or across the desk. Think about how well you know your spouse or your close friends – they would be an easy sell because you already know their background and their situation. The more strategic questioning you practice, the more you’ll uncover and the more effective salesperson you’ll become.

About the author

Nick Kane

Nick Kane is a Managing Partner at Janek Performance Group. He has trained more…

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