How to ask powerful sales questions

by Steli Efti

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.

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

Don't just interpret your prospect's answers. The less you base your understanding on assumptions, and the more detailed responses you elicit, the better in sync the prospect will be with you.

Here's an example.

Prospect: "Ease of use is really important for us."

Bad sales rep: (assumes: oh, they want a slick user interface and easy onboarding) "Oh great, our software is really easy to use!"

Great sales rep: "Ok, what precisely do you mean when you say ease of use? What about the experience needs to be easy? The initial setup and deployment in your organization? Or the usability for the end-user who'll work with it daily? Do you have an example of an application you're working with now that is easy to use? This would help me to precisely understand what you're looking for when you're thinking about ease of use."

So when a prospect gives you an answer, ask follow-up questions that go deep, that explore things in more detail. This will a) help you gain a better understanding of the prospect's wants and needs and b) show the prospect that you care and are truly listening to him.

Just by doing that, you'll stand out from 90% of all the other sales reps from competing vendors. If a prospect feels truly understood by you, they'll trust you and feel better about you and your product

Great follow up questions to ask

These questions aren't rocket science, they're pretty straight-forward.

  • What does that mean?
  • Do you have an example of that for me?
  • Can you tell me more about this?

Let's say a prospect tells you that five people will be using your software. Rather than just taking note of it and moving to the next question, you can ask further questions:

  • Ok, tell me about these people. Have they been with your organization for a long time, or have they just joined? 
  • Will these people keep using it for a long time, or is this typically a high-turnover position? 
  • What's their workflow like? 
  • Are they all working from the same location? 
  • Will this team grow over the next 12 months? If so, how? 
  • How do they communicate with each other?

The exact questions you ask, of course, depend on the specifics of your product and their organization.

Record yourself

Just use what you learned here about asking questions in sales to improve your next sales calls. Record them and listen to how you're asking questions.

Our sales CRM makes it easy to record your calls automatically and play them back as MP3 anytime you want. Studying your own sales questioning approach this way can help you to quickly take your sales game to the next level.