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Are Your Teams Asking the Right Questions on Sales Calls?

3 min read

Of all the skills and tools that comprise a good salesperson’s arsenal, there is none as important as questioning. But there is an art and science to proper questioning, from the speaker’s tone to the context in which questions are posed. In this post, our focus will be on the content side of questioning.

We tend to be more comfortable asking fact-finding, information-seeking transactional questions.

They get us the facts, data, and information we need in order to scope out an opportunity. Though they may not be the most creative or innovative questions we ask, they are absolutely necessary. We have to ask them, as do our competitors. Our clients expect these types of questions.

Generally speaking, we usually have no problem asking needs clarification questions.

These are open-ended questions that get the client talking about their needs and problems, objectives and challenges, concerns and aspirations. As we ask these questions, we dig beneath the surface. We can be creative and innovative. We can begin to differentiate ourselves.

But most of us don’t ask many strategic questions.

That is unfortunate, because these types of questions are the best differentiators of all and can have the most impact. What makes these types of questions so critical?

Strategic questions

  1. get clients thinking long term—they stretch their imaginations and help them visualize where their business is going
  2. uncover unconscious needs
  3. elevate an otherwise predictable conversation
  4. help move your organization up the Value Pyramid
  5. enable your salespeople to learn more about the direction of the client’s company
  6. can result in the client sharing their fears about the business, which will enhance the relationship
  7. make your team member look more like a consultant than a salesperson.

Here are a few examples of strategic questions that your teams might ask a client:

  • Where would you like the business to be 4 or 5 years from now?
  • What might prevent you from reaching your long-term goals?
  • What changes do you anticipate in the long-term demands of your clients?
  • How will you leverage the success of the last five years to continue that extraordinary growth long term?
  • What threats do you think may present themselves in the future that you haven’t dealt with in the past?
  • What do you see as your most significant long-term opportunity?

With such a lengthy list of benefits, it’s a wonder why salespeople don’t ask strategic questions as often as they should. One reason is that they don’t always have the time to devote to planning them out. Strategic questions don’t just roll off the tongue—your team will have to invest some time in getting them together and figuring out the perfect combination of content and delivery. But it is time well spent.

Another reason salespeople don’t ask strategic questions is that they don’t want to make their clients uncomfortable. After all, if the client is stumped by your sales team’s questions, how does that leave them feeling? Your people can cut this risk simply by starting with a pre-question statement—this prepares the client for the question to come, and gives them a chance to consider a response. Even if they still don’t have a great answer, they will remember your salesperson as the one who made them think. That will work to your advantage every time.

Your teams don’t have to ask a ton of strategic questions in one meeting. Ask two, maybe three over the course of a sales call. But they need to ask them. They will learn more about the client, demonstrate their value, and clearly differentiate your organization.

What’s your favorite (or most commonly used) strategic question? Share it with us in the comments below.


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