Insight Selling Questions to Boost Your Success Rate

BY Rachel Cagle
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Do you know what insight selling is? According to Mike Schutlz, writing for RAIN Group, it’s, “the process of creating and winning sales opportunities, and driving change, with ideas that matter.” Sales reps do this by, “Providing value in the form of creating insights through buyer and seller conversation,” and “Selling a particular idea or strategy a buyer should pursue but might not know about.” Before you can provide value or sell ideas, you need to ask the prospect the right questions. Schultz says that these questions are:

  1. Why?”
  2. What have you tried?”
  3. Have you considered…?”
  4. How do you know that?”

Questions for Successful Insight Selling


You know when you tell kids to do something, but they don’t understand the justification behind it? They’ll ask you, “Why?” over and over again until they get a satisfactory answer. While you should never just repeatedly ask “Why?” when working with a prospect, why-​based questions will get to the bottom of the their motivations.

For example, say you’re discussing the prospect’s current strategy, and it either doesn’t make sense to you or you feel that they’re better off doing something else. If you ask, “Why is that your strategy?” they can give you a good reason behind their choices and you can then discuss the related pros and cons. Or they’ll fail to be able to justify their decision-​making. Either way, their response will give both of you insight into their way of thinking. And that’s the basis of insight selling.

What have you tried?”

Obviously, if the prospect is meeting with you, something has gone wrong in their current operations. When you ask the insight selling question, “What have you tried that hasn’t worked?” you’ll be able to make mental notes about how to compare your product or service to what the prospect has previously experimented with. “This question will help you understand their thinking and help you see the gaps between what they know won’t work and what you know will,” says Schultz.

Have you considered…?”

Remember, one of the keys to insight selling is presenting your prospects with opportunities they have not considered before. You can explain the ins and outs of how your idea could benefit them. Or you can discuss their previous experience with your suggestion and how you can work together to make a second go at it successful this time around.

How do you know that?”

Your prospects may reject your proposal and leave you wondering why they did so. When you ask, “Why?” they may give you a reason based on their perception of the facts. You, the industry expert, however, may know that their reasoning is either flat out false or outdated. If this is the case, politely give them evidence against their stance. Continue the conversation in a way that will allow the prospect to come to a new conclusion on their own, based on facts instead of telling them that they’re wrong.