Years ago, the manager of a large conglomerate asked me to help a struggling new salesperson. Everyone called him Buzzcut Bruce. Bruce was new to sales. As it turns out, he had excelled as a private investigator in Louisiana, but after moving to Colorado he thought he’d take a whack at a career in sales.

Whenever I coach a new salesperson I focus on the discovery questions they ask their clients. Bruce asked the right questions, all right, but his questioning quickly deteriorated into interrogations. Not a good idea. Here’s an example:

“So, Melinda, you just mentioned you’ve been using Thimble Fish as your technology platform.”

“Yes,” the prospect would reply. “When we founded the company, that’s all we really needed.”

“And when did you open your doors for business?” he’d ask.

“Late August 2012.”

Painful pause …

“Hmm … but you said earlier that you’ve used Thimble Fish for nine consecutive years. Assuming you licensed it 2012, that would mean you’ve used it for five years. Which is it, ma’am?”


I couldn’t tell if he was trying to get a signature on a contract or extract a confession.

Now, this is an extreme example of what not to do. Not all novice salespeople are going to grill their prospects as hard as a former private eye. But my point is this:

Unless salespeople are truly curious, the discovery process may feel like an interrogation to customers.

You may understand the power of thoughtful discovery questions. You may have memorized what questions to ask and even know precisely when to ask them — only to completely annoy your customers. Why? Let me be blunt. Many salespeople, in their misguided attempts to uncover valuable information, display a lack of genuine curiosity.

It’s never enough to ask questions; you actually have to listen for and care about the answers!

You may ask the perfect question … and then, BAM, as soon as the customer gives you an opening, you start spewing out all kinds of product information. You just can’t help yourself. I call this the “shotgun approach.” We fire off feature after feature, hoping that one of them will hit its target.

Research suggests if you give someone too many options, eventually that person will just stop paying attention. Our brains are configured to make a certain number of decisions per day and once we reach that limit — our saturation point — we can’t make any more, regardless of how important they are. Former President Obama has been quoted as saying that he makes his most important decisions in the morning while he’s still fresh. Salespeople must keep their presentations simple and on point to keep customers engaged.

My recommendation?

  1. Ask questions that help you better understand your customers — not simply those that allow you to elbow in your point of view.
  2. Do your homework before you meet a prospect. Who is this person? How long has he or she been with the company (what you don’t want to do is pre-judge).
  3. Dig deep to find out what really matters to your customers at the heart level.
  4. Get to know your customers’ inner worlds and discover how it affects their outer worlds.
  5. Instead of reacting negatively, seek to understand why a prospect might be putting off a decision.

Asking thoughtful questions isn’t simply a matter of methodology; it’s a matter of mentality.

It’s about adopting a mentality of investigating over dictating, learning over teaching and understanding over closing.

Adopting a curious mind-set may not help you convict a suspect, but it will certainly help you sell a prospect.

Unless salespeople are truly curious, the discovery process may feel like an interrogation to customers.”

Shari Levitin | Trainer, Speaker and Author of Heart and Sell
Learn from the best. Sell like the best.