INSIDE Inside Sales – Ep 127: How to Ask the Right Questions

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Asking leading sales questions is a great way to get to know your prospects, but do you know how to build the right framework around those questions?

In this episode of INSIDE Inside Sales, Darryl and Scott Kaplan, the rockstar sales coach with Quick Hit Sales Tips discuss the power that effective questions can wield and teach you how to dig deeper during discovery. They will also share valuable advice on how to craft the questions you need to be asking, show why pitching must come later in the process, and share Scott’s unique “F-A-C-T” discovery process for getting the quality information from your prospects. Subscribe now and learn how to close more deals by asking the right questions.





sales questions that convert

How To Ask Sales Questions That Convert


  • To build sales relationships with more potential, drop the canned pitch and focus on asking quality questions. Get to the why and you’ll find gold! 
  • Scott Kaplan of Quick Hit Sales Tips explains where most sellers do well in getting to know their prospects and where they could use a bit of guided curiosity.
  • Scott shares his easy framework for coming up with the right sales questions. He tells us how to apply it to both the qualification and discovery stages.
  • Gear your questions toward outcomes to help your prospect envision themselves using your product or service.

If you have kids — or even if you’ve only met one! — you know how often they ask the famous question: “Why?”

That can get annoying fast. But it’s not the question that’s the problem. 

In fact, why is something we should be wondering and asking a lot more as adults. That’s especially true when you’re in sales.

Scott Kaplan of Quick Hit Sales Tips is the question guy; he’s trained thousands of sales reps and managers to ask effective questions. I got to pick his brain about asking good ones on an episode of INSIDE Inside Sales.

If you’ve ever gone through your list of standard sales questions and wondered why you’re still not closing the deal, you need to hear Scott’s expert advice!

Find your innate curiosity

First, you have to lay the foundation for delivering the right questions to your prospect. It all starts with being curious about who that person is and what they want to achieve — in business and in life.

Genuine curiosity can be a huge asset when you’re getting ready to interact with brand-new prospects. There’s a good chance you had a case of the “whys” when you were young, and Scott encourages you to tap into that again.

In this case, you should do the opposite of what most people would tell you: Don’t grow up! At least when it comes to being curious, give yourself permission to channel your inner toddler. 

Boost sales questions with the F-A-C-T framework

Real interest only makes a difference if you have the awareness to apply it.

Luckily, Scott has an easy-to-remember framework for coming up with the best sales questions: F-A-C-T. 

  • Fundamentals: These are the things Scott says you’re probably already doing well — the basics you collect to score a lead long before meeting with them. Those include their history, role, environment, etc.
  • Ability to Move Forward: Next, you need to determine the prospect’s stage in the journey. Will there be approvals necessary before they can commit? Are they truly poised to purchase?
  • Commitment: In this stage, we want to find out how much a prospect wants change. Are they willing to take your solution and run with it?
  • Timing and Prioritization: What if they’re eager, but not prepared to practically implement or install what you’re offering? Find out!

Understand qualification versus discovery

The F-A-C-T approach applies to all roles on a sales team because there are layers to each letter in the framework. Yet, before you can walk through the F-A-C-Ts, you’ll want to be sure you’re dealing with a qualified lead and not confusing qualification with discovery.

Qualification means figuring out if you want to pursue the lead in the first place, says Scott.

He adds that SDRs and BDRs should aim to collect three major categories of information in the qualification process:

  • Account: Find out if the business is aligned with what you offer.
  • Contact: Don’t underestimate the power of knowing “small” details like how to pronounce someone’s name, their role and title, and what they look like. It can mean the difference between having a fantastic in-person encounter and royally messing it up.
  • Need: Here’s where you want to apply that curiosity. It’s where you close out the Fundamentals and move the lead forward to the next step.

Discovery means diving deep into the prospect’s pain points if and only if they’ve already been qualified.

Tap into a bit of sizzle

Once you’re well into the discovery stage, Scott recommends asking questions that allow the prospect to picture a fresh scenario for their business. But, sometimes, you need a bit of backup to make that happen.

A teaser — i.e. a software demo — is a great example of backup. It’s concrete and gets the prospect thinking of their business’s future, rather than just the back-and-forth conversation you’ve been having. 

After seeing your real and applicable solution, which Scott calls “the sizzle,” it becomes easier for them to imagine themselves implementing what you’re offering. That’s when your questions take on more meaning.

Align your team with a focus on impact

Your SDRs, BDRs, AEs — every one of your salespeople — should be trained on the value of sizzle and how to pair it with what Scott calls impact-style questions. These questions are valuable because they represent an outcome, not just an idea.

There are both negative and positive impact-based sales questions, and it works best when you combine the two.

Scott shares some examples of questions that get at how the prospect is being hindered:

  • What’s currently limiting your ability to reach your quarterly goal?
  • What negative impact are you seeing from the absence of a [insert your industry] solution?
  • What would you say will be your biggest roadblock in the coming year?

And some that are focused on what the prospect can gain:

  • What could your business achieve with [x number] of new clients?
  • How could you use [insert the name of your solution] to strengthen your team?
  • In what way might you benefit from implementing a new system? 

When your entire sales chain understands how to stir your prospects’ interest in their potential outcomes, you start to see tangible internal outcomes too.

Ask great questions — then wait!

Now, you know how to prepare a list of awesome questions. But do you know how to leverage those to figure out what matters?

Questions might spark a conversation, but the learning happens after you’ve stopped asking. In true kid fashion, you have a chance to absorb details like a sponge every time you get an answer to one of your whys. It’s a matter of whether or not you choose to pay close attention.

“We forget to take that step back and really make sure we understand what we’re trying to solve and help the customer understand what they need to solve,” says Scott. 

Scott points out that this is often the piece his sales trainees miss.

That’s because it involves patience, and this is where you have to combine your adult maturity with that childlike curiosity. The impact of your questions will be lost if you push too hard — or have what Scott calls “happy ears.” 

When you’re jumping in to solve problems instead of listening, you could ironically miss out on the gem that’s gonna make the deal happen.

Go get those F-A-C-Ts right, but then it’s time to listen and let the answers guide you.