5 Most Powerful Sales Questions To Ask Without Sounding Salesy

A successful sales rep is a curious sales rep. And when you ask potential buyers the right questions during discovery, you’ll get some powerful takeaways to better qualify leads, drive enthusiasm, and boost your chances of closing.

In today’s post, I’m breaking down five of the most powerful sales questions to ask potential buyers. And best of all, these questions let you avoid sounding salesy while demonstrating yourself as the sales expert you really are.

Best Sales Questions

These days, successful sales isn’t just about being chatty. Sure, the gift of gab helps. But when it comes down to it, charm alone isn’t enough to seal the deal.

Instead, you need to be able to explore issues, dive into problems, and offer exceptional solutions for your buyers. You need to offer value, not just a pitch. And asking questions is the best way to investigate whether your buyer’s problem is one that you can solve.

But there’s a catch here—asking the wrong questions can set you up for failure. I’m talking about close-ended and manipulative inquiries like “Tell me, would you be interested in doubling your revenue this quarter?” or “What will it take to earn your business?”

These types of questions are downright shit at getting real, valuable info you can use. And beyond that, they make you sound like a slimy sales rep that no one would trust.

So rather than falling back on those sales cliches, start asking these five powerful sales questions instead. Doing so will let you qualify leads and give you the info you need to skyrocket your sales success.

So, question one…

1: “Does It Make Sense to…?”

This is one of my personal favorites because it virtually eliminates the need to “close” on deals. You know, when you’ve spent days or even weeks on a potential buyer and then nerve-wrackingly have to ask them for their business.

Closing that way sucks. And it puts a lot on the line, too. If they walk away, you’re out tons of lost time.

But when you ask this clever sales question along the way—I mean when…

“Does it make sense to set up a call?”

Setting up discovery calls…

“Does it make sense to schedule a time so you can see it in action?”

Moving on to demos…

“Does it make sense to bring in our product team to dive deeper into the specs?”

Discussing product specs, all of it…

When you do that, you’re getting continuous buy-in from the prospect.

Plus, buyers will have the opportunity to tell you exactly what’s holding them back from taking the next step, giving you the chance to address any of their nagging objections.

Best of all, you get to avoid all that nail-biting of the “will they, won’t they” right before you ask for your business.

2: “Why Can’t You Solve This Problem Yourself?”

Why can’t you solve this problem yourself?

This one in particular is great for qualifying leads.

On the one hand, this question helps you uncover more about the problem and the obstacles you might face as you try to solve it. And maybe a prospect that seemed like a good fit turns out not to be a match as a result.

But beyond that, this question also lets you evaluate their need. Do they even need you? In most industries, the clients you want to work with won’t be able to do the same job your product or service is doing. Otherwise, you’ll likely run into plenty of issues down the line, like questioning your judgment or asking for the job to be redone entirely.

If they can solve the problem themselves, they’re not going to value what you do as much as they should. And it’s better just to move on.

3: “When Do You Need This Solved By?

This powerful sales question gets to the heart of one of the most important issues—timeline.

Are they hoping to solve the problem in a few weeks, but your product requires a two-month implementation? Are they planning ahead for a few years from now, and only wasting your time today?

Answering these and more timeline questions is an important step for qualifying your leads. And it’s a solid filter that weeds out those that aren’t a fit.

4: “How Would Things Be Different If We Solved This For You?”

Think of this question as an investment in the future satisfaction of your product. Let me explain what I mean here.

For most of you out there, your product or service is going to take some effort on the part of the buyer. Maybe they’ll have to fight for budget. Or spend time on training. Or maybe even hire a new team entirely to use your product to its full potential.

It’s vital that this effort is well worth the benefit your product provides. If it isn’t, your buyer will feel resentful, won’t provide referrals or great reviews, and likely won’t be coming back for return business.

Asking this question puts this required effort into perspective for the buyer. If it doesn’t match up and they leave, you’ve just saved yourself loads of hassle later. And if it does, you’re building enthusiasm in a prospect that’s a picture-perfect match.

Easy peasy.

Okay, and the final powerful sales question I have for you today is…

5: “How Are Projects Like This Usually Funded?” 

How are projects like this usually funded?

Yep, here it is—the money question. People get weird about money, don’t they? Jaws tense up, prospects close off, and the air gets sucked out of the room in an instant.

But when you approach budgetary issues with this question, you’re easing into it. Prospects may talk about whether they have the funds allocated already, if this is a single department’s expense, and may even hint at their desired timeline too.

Plus, it’s phrased in such a way that prospects won’t feel like they’re being blindsided, keeping them open, friendly, and engaged.

This final question is a simple solution to a touchy subject. And it can quickly shift the tides of any discovery call in your favor.


Success in sales is all about bringing real, tangible value to the table. And delivering that value means you have to be adept at uncovering your buyer’s problems, assessing their needs, and determining if you’re a good fit for each other.

To do all that and more, just ask these five powerful sales questions…

  • “Does It Make Sense to…?”
  • “Why Can’t You Solve This Problem Yourself?”
  • “When Do You Need This Solved By?
  • “How Would Things Be Different If We Solved This For You?”
  • “How Are Projects Like This Usually Funded?”

With these questions, you’ll be able to qualify leads faster, tap into real buyer needs, and speed up the sales process—all while never sounding salesy and showing off your sales expertise at the same time.

So next time you’re on a discovery call or delivering a pitch, make a mental note to ask these five questions along the way to make your job ten times easier.

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