Everybody who wants to be great at sales needs to master one skill: the art of listening. The better you become at listening, the more you sell. And the better you get at asking sales questions, the better you get at listening.

But don’t be the passive listener whom the prospect uses like a psychotherapist, babbling on about whatever he wants to get off his chest. Great salespeople actively direct the course of a conversation by asking astute questions.

This sounds great in theory—but try putting it into practice, and you’ll see how hard it is. Prospects quickly become uncooperative, antagonistic or flat out tell you that they don’t want to answer your questions.

Why do these prospects have to make your job so difficult? Why do they put up their defenses just because you ask them a couple of qualifying questions? I’ve got good news for you: It’s not your prospects that suck … it’s your questioning technique.

Fortunately, you can hone this skill.

How NOT to ask questions in sales

These are the most common mistakes I see sales reps commit when asking qualifying questions:

  • Robotically going through a list of questions. If the prospect feels like you’re just pushing them down a sales assembly line, mindlessly going through the motions and just following protocol without really caring about their responses … don’t be surprised if they quickly become uncooperative. Don’t be a “survey salesman”.
  • The fake “Great!” response to every answer. Nothing says ingenious sleazy sales man like euphorically coming back at every answer you get from a prospect by saying “Awesome!”. It’s disingenuous, and prospects have very sensitive antennas when dealing with sales reps.
  • Interrogating your prospects. How do you feel when someone pushes you around or treats you like a subordinate? Some salespeople try to compensate for their lack of skill by being overly authoritarian, and while this approach tends to work with a certain percentage of prospects, it will mostly result in resistance and push-back.
  • Anxiously asking. On the other end of the spectrum, you have the nervous salesperson who’s carefully whispering questions, as to not risk disgruntling the prospect with a question he doesn’t like. When you’re dealing with a prospect, you always want to operate with benevolent power.

There are many ways to improve your questioning techniques, but to become really great at asking questions, you need to shift into a different mental gear.

Care and curiosity

When you bring a genuine sense of curiosity, a real interest to the table, and truly care about providing value to them, it will affect the way you’re leading the conversation with your questions.

It’ll change the way you ask questions, and the prospect will be more cooperative and provide you with the answers you need to move the sale forward.

Less interpretation, more elicitation

From his success on the sales floor of an automotive dealership  to becoming a veteran trainer and then the adoption of technology for Internet-based marketing, his career has evolved to deliver the skills and tools needed to help consumers. Richie Bello combined his automotive expertise with his robust desire to “take care of the customer first” to become an automotive influencer, published author, and renowned trainer.  Bello absorbed the wants and needs of consumers as he worked up the ladder of the automotive industry.

Over the thirty-five years of his career, he developed strong Internet marketing skills, leading him to developing software solutions that create ease for consumers, and helps dealers improve relationships with customers. Innovation drives success. And, for Bello, it’s in his DNA. took years to come to consumers and arrived in a timely manner, during the 2020 Pandemic. With over 6 million vehicles on the site, features that help consumers deliver, finance and warranty, Bello has met the retail digital age head on.

Bello also is founder of Richie Bello Institute of Leadership and Management, a 501C3 not for profit, dedicated to the recruitment, education and employment of veterans into the automotive industry. Visit


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