How To Deliver Insight & Challenge The Status Quo With Questions

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Discovery Template & Guide LI-Phoeonix

In the 2012 Harvard Business Review article titled “The End of Solution Selling,” the Challenger Sale positioned itself as the dominant sales methodology by creating a false dichotomy:

  1. Ask information-rich customers generic questions, or
  2. Challenge them with insight.

But what if salespeople asked better questions than “What keeps you up at night?” Could questions rise from the ashes like a phoenix if salespeople traded generic questions for ones that are insight-directed?  


When customers understand their problems, it’s easy for salespeople to lead them through discovery. In other words, customers don’t need salespeople to shine the light of insight on issues they’re already aware of. A salesperson can simply confirm the value of his/her product by asking generic questions. These customers don’t need to be challenged, because they’re already motivated to change.     


But when customers don’t fully understand their problem, salespeople will not be able to confirm value with generic questions because there is simply no value to confirm. The answers to the generic questions are hidden just out of sight, because the customer can’t determine the cost of his/her unrecognized or misunderstood problems. In these cases, the salesperson’s product will be seen as a “nice-to-have” instead of a “must-have.” It is crucial that salespeople create value by challenging these customers with insight-based directed questions.

With insight-based directed questions, salespeople illuminate the problems and costs of not having their unique capability or product (see create value in the Discovery Questions Template). Unfortunately, most salespeople are not able to create value with directed questions, because they don’t know where to shine the light of insight. Without a helicopter view of the customer’s world, most salespeople only see what’s directly in front of them. Hence, they lack the visibility to ask appropriate second or third follow-up questions that challenge the customer’s status quo.

As a result, salespeople can only help customers become aware of superficial reasons to change, like that their current system is prone to error or lacks timeliness. Awareness of these superficial problems does little to inspire customers to change.

The top 10% of salespeople, however, are able to combine product and customer knowledge, and thereby achieve what I call “sales wisdom.” They know where to shine the light of insight with directed questions, so that the customer is able to discover the problems and resulting costs to their operations if they don’t consider the salesperson’s product.

To inspire change, star performers show customers that the risks of the status quo feel greater than the risks of change. With directed questions, they transport the customer to the risks of the status quo within their own company. This simulated experience is powerful, because customers are not only made aware of the risks intellectually, they feel the risks in their gut.

Most salespeople simply tell customers the risks of the status quo. This approach is weak, because the abstract risks of the status quo don’t feel as real as the concrete risks of change. No wonder the majority of enterprise sales opportunities end with the customer deciding to stick with the status quo and not buy (see my Harvard Business Review article, “When to Sell with Facts and Figures, and When to Appeal to Emotions”).    


How do you get all of your salespeople to develop sales wisdom so that they can challenge the status quo and create value as well as your top performers? Many might suggest that you supply your salespeople with a list of questions, but this is not a good strategy. In the heat of a sales call, you can’t expect them to remember 50 to 100 questions. In addition, the buyer’s responses could bounce from question 6 to 23 and then back to 3. Your salespeople will get lost in a sea of required questions, because the sequential nature of the list is too inflexible to adjust to the fluidity of a real business conversation.

It may sound counter intuitive, but if you want your salespeople to be more effective at creating value with insight-based questions, you must give them the answers.  


I’m aware of the challenges salespeople experience when they deliver questions, because I was a partner at a question-based sales methodology for 5 years. What I discovered was that the people who attended the messaging workshop to create the questions in preparation for the training were successful at solution selling. By knowing the answers, they didn’t need to memorize questions, because they saw the big picture. They knew where the questions were headed. This enabled them to easily pivot with the customer on a sales call, and then walk 3 to 5 questions deep into the customer’s world in order to illuminate unrecognized value.

If you want your salespeople to uncover unrecognized value with insight-based questions, first tell them the story behind the questions. Once they see the answers to the questions as a story, they will be able to use them in the heat of a sales call. People are 12.6 times more likely to remember facts and figures when they are presented in the form of a story (Made to Stick, p. 243).


Before salespeople can build credibility by asking these types of questions, they first need to build trust. This means meeting the customers where they are. If a customer’s buying vision is on target, the salesperson need only confirm value with generic questions. But if it’s off-target, they will have to challenge the status quo by asking directed insight-based questions.


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