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Sales Enablement  |   Sales Process  |   Sales training

The Secret To More Sales: Asking Better Questions

Chris Duprey

By Chris Duprey

Oct 2, 2023

In any sales call, the quality of the outcome is only as good as the conversation you have. And your conversation will only be as good as the questions you ask.

Questions are the tool you use to really get to the heart of the matter because the right questions can prompt real reflection.

Every day, salespeople squander their chances to ask great questions, instead reverting to the default, useless questions we’re all used to.

It’s time to replace placeholder, run-of-the-mill questions with incisive, stop-on-a-dime questions that really do what they’re designed to do.


I’m not saying you should turn your sales calls into interrogations or therapy sessions. Rather, this is about serving your customers by asking a great question — and then shutting up so we can actually listen. 

Refuse to settle for useless questions

The professional world is filled with useless placeholder questions that we use out of habit. You know the kind. Honestly, you hear them so often it feels like a tired little bit of theatre you’re performing:

Salesperson in a store: Can I help you?

You: No, just looking 

Server in a restaurant: How is everything?

You: Fine, thanks.

Checkout person: Are you interested in hearing about our rewards program?

You: Not today.

Questions like these are expected, routine, and pointless. 

We need to retrain ourselves (and the people we manage) to recognize opportunities to insert better questions into our interactions so the conversation becomes richer and more meaningful. 


Now keep in mind, better questions don’t have to be more complicated. 

In fact, they’re usually simple — but they’re specific and intentional, and well-timed. And, in turn, they’re better tools for the outcome you’re after. 

Let’s look at some ways we can use better questions as salespeople.

Asking better questions in sales meetings

Sales meetings are the bellwether of your company’s future. The way your sales conversations go is the way your company will go. In most cases, the salesperson is the first face your buyer sees — so they have the responsibility for making a great first impression for your brand. 

And we all know what they say about first impressions.

the-secret-to-more-sales-asking-better-questions-03 (1)

Therefore, it is crucial that salespeople come off as curious, genuine, and, most importantly, invested in the buyer’s success. You can’t do this unless you get to know your buyer. You can’t get to know your buyer without asking questions.

But not all questions are created equal. Below, let’s look at some sub-par questions that we use in sales — and then some better ones we can replace them with. 

Generic, boring, obvious questions

Too often, we cloud meetings with the same useless questions that sound more like an online form than honest conversation starters

I’m talking about checklist-type scoping questions that sound like a questionnaire come to life.

  • What do you do? 
  • What does your company do?
  • What’s your budget?
  • What’s your timeline?
  • What are you looking for?

It’s not that these are bad questions. But they’re insufficient if they’re the only ones you’re asking. Just like the “Can I help you?” question above, these questions prompt quick answers with no deeper thought. 

These questions are obvious and unhelpful because they don’t spark meaningful conversation. They get answered in half a sentence, and the sales rep has to quickly jump back in and fill in the silence.  

Better questions that actually prompt real answers

Better questions get better answers. 

Instead, ask simple, clear, specific questions that prompt real thought and real dialogue:

  • What’s the single greatest challenge you are having with your __________ right now?
  • Tell me about your last time buying a similar service. What about that experience was disappointing?
  • Why are you looking to make this purchase now? 
  • If you go ahead with this purchase, how does your life look different in six months?

Think about what makes these questions better. Yes, they’re specific and clear. But the biggest thing is this: They don’t prompt an automatic answer. (Remember, when questions can be answered without much thought or reflection, they lose their power.)


When you prompt self-reflection in your potential customers, you help them start to understand their own challenges in a way they might not have before. In doing so, they build a trusting relationship with you. 

But remember, great salespeople balance both types of questions. Think of it like a date. You want to ask good questions to get to know the person, but you’ve also got to warm them up. So, you probably don’t want to start out with “Tell me about your worst memory from childhood.”

Remember ‘The Law of 3’

Marcus Sheridan likes to say that the answer you’re after is at least three questions deep. In other words, a single question might not get to the heart of the matter. People are so used to giving surface-level answers that sometimes sales reps need to ask a question again (or a variation of a question) to get to the good stuff.

This is The Law of 3.


You ask: “Why are you making this purchase now?”

They say: “Well, we’ve been thinking about it for a while.”

So, you ask: “That’s great! But what’s prompted you to reach out to us now?”

And you get: “Well, it’s the end of our fiscal year.”

You follow up with: “Yes, but that means you’ve likely had this budget earmarked for a while. So, why now?”

And you hear: “We’ve got a big product launch in the next six months, and we’re concerned we’re not going to do it justice to stay relevant in the marketplace. This purchase helps us shore up some potential shortcomings so we can control how we go to market.”

Bingo. That’s the gold you were digging for. Now you know what you’re dealing with. And if you stopped early, you wouldn’t have gotten it.

Questions are the key

To be a great salesperson today you need to be a great communicator. It’s not a killer sales pitch. It’s not a perfect slide deck. It’s human connection based on genuine curiosity.

When you ask better questions, you break down barriers, you establish trust, and you get to the real issues facing the person in front of you. 

At IMPACT, we train sales teams to win through candor, curiosity, and teamwork. To learn more, reach out to me, Chris Duprey, to see what’s possible. 

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