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Gap Sell Keenan 64: Asking the Right Sales Questions

A Sales Growth Company
October 21, 2023

If you’ve watched enough Gap Sell Keenans, you know, one of the top 3 problems salespeople have is not asking the right sales questions. They don’t fully understand where they are trying to carry the conversation or they get lost along the way. Asking the right questions in a sales discovery call is an art and you want them to lead you to a problem as quickly as possible. We don’t want to waste our time as sellers or the prospects time inching our way to a problem.


Sales Myth: Ask Lots of Questions

I keep hearing “ask lots of questions” being pawned off as sales advice. The idea that asking a lot of questions is the cornerstone of a good salesperson is doing more harm than good and it’s time we change that.


Sales Questions with Purpose

Asking a lot of questions won’t magically transform you into a top-level sales pro. In most cases, you’re more likely to annoy your buyers, which causes a ripple effect. You annoy your buyer, they start to see all discovery as a waste of time, and eventually they’re increasingly unwilling to take a call.

Asking endless questions is not the trick to successful selling. Having the wisdom to understand which questions to ask and understanding the purpose behind those questions is the real “secret.”


Separating Crucial from Trivial

“Ask lots of questions and listen” sounds great in a LinkedIn post, but in practice, it’s misguided. Very few, if any, salespeople, or organizations grasp what information they need from a buyer. And even fewer understand which information can tip the scale in their favor.

Understanding who the champion is or deciphering the buying process is important, but they are absolutely not essential.


Discovery Call Assessment

Take a moment to reflect on your recent discovery calls:

  • What are the fives pieces of information you’re seeking from the buyer?
  • Why do those five pieces of information matter?
  • How does this information make a difference to me winning or losing this deal?
  • How critical is this information to winning or losing the deal?
  • How did I come up with this list?
  • What evidence do I have that this is the right information?


Is it in the CRM?

Once you’ve done that, go look at your existing opportunities. Did you get all that information for every deal AND did you get it all in the CRM?

If you’re honest with yourself, you might find that your answers are along the lines of “I don’t know, I don’t know, I don’t know, etc.” When it comes to storing this information in the CRM, it’s a resounding “no.”


How Aimless Questions Affect Your Buyers

We have no idea what we’re truly trying to uncover in these sales conversations. We can’t differentiate between vital and less important information. Which, unfortunately, forces the buyer to perceive the discovery as a formality, a checklist item, that serves little to no purpose.

This all boils down to the fact that we’re asking a plethora of questions without any clear direction or objective in mind.


Quality Over Quantity

As a collective, the sales community is infatuated with catchy phrases that confirm our expertise and competence. But we rarely delve into the depth and execution of these ideas. Winning a deal isn’t predicated on the volume of discovery questions, it’s about the volume of the RIGHT questions.

Real selling lies in asking the right questions with a purpose. Take the time to identify what information, for both you and your buyer, is crucial in determining if and why they should make a purchase. In this week’s episode, Matt does a pretty good job of that. He knows the problem he can solve and he asks questions directly to get to answer “does Keenan have a problem I can solve?”


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