Question-Based Selling: Why Most "Closers" Fail
Sales Guides
min read

Question-Based Selling: Why Most "Closers" Fail

When used effectively, question-based selling is a strategy you can depend on to consistently close deals. Learn what it entails, how to use it successfully, and the challenges you might face along the way.

Kayvon Kay
Kayvon Kay

February 25, 2022

And What You Can Do to Fix It

If someone were to tell you the key to closing high-ticket sales was about asking the right questions, you wouldn’t be surprised, right?

After all, you already know that question-based selling is the best way to sell.

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However, what you might not realize is that you could be doing it all wrong. You might be asking the wrong questions, which is negatively impacting your closing rate. Most people have the same problem, but the good news is that you can fix it. 

There are usually multiple levels to a prospect's pain.

In this article, you’ll learn about what effective question-based selling entails, how to use it successfully, and the challenges you might face along the way.

The Problem with Question-Based Selling

Done right, question-based selling can become your superpower. It will help you close more deals than you ever have before. 

Done wrong, however, it can develop into your biggest weakness. This is the risk and reward of question-based selling, but the “experts” only tell you about the latter. They focus only on how powerful question-based selling is, but they fail to provide what it takes to actually do it correctly.

It’s not enough to sit there and ask questions. If you have a list of them in front of you, and you read from a script, you’ll fail.

  • Instead of building trust, you create skepticism.
  • Instead of closing the deal, you invite objections and resistance.
  • Instead of solving their problems, you highlight more of them.
  • Instead of learning about what your prospect needs and how you can truly serve them, you force them into having what you want them to have.

This is not the point—and this is not how a high-ticket closer approaches a sales call.

Identifying the Cause

Most of these problems come down to you entering the sales call with an agenda. If you do this, you’ve failed before you’ve even begun.

This isn’t to say you shouldn’t turn up prepared or have an end goal in mind. You need these things to succeed.

On the other hand, having an agenda doesn’t serve you. The reason is simple:

It backs you into a corner. The moment the call steers off course, you panic. You become desperate. Instead of listening to your prospect, you try to force them into what you want.

This is not a good mindset to have. This is not how a high-ticket closer operates. It’s what a desperate salesman does.

How to Fix It

If your goal is to become a gifted, elite high-ticket closer who provides massive value to those you serve, you’re in the right place.

In the following sections, you’ll get to learn the secrets to question-based selling, including what you need to consider to do it correctly as well as some examples to help you visualize your success.


One of the most common questions that sales professionals ask is, “How do I know when the time is right to start asking questions?”

The simple answer is that it’s always the right time to do so. The moment your sales call begins is the moment you enter question-based selling mode.

It isn’t about when to ask questions; it’s about knowing how to. You need to know which ones to ask and why those are the most important. This is why entering a sales call with an agenda is never a good idea. It prevents you from adapting to the situation.

This is the mindset you need to get into. It’s about knowing which question is the right one to ask at any given moment. 

To do this, you need to listen.


As a sales professional, your job is to listen. Pay attention to your prospect. Don’t read off a script or work through a list of pre-written questions.

You need to listen to your prospect to understand what they need. Show that you truly care about them by just listening to what they’re telling you.

That’s it. Listening is one of the most powerful tools you have. When you listen properly, the sales often close themselves. When you listen, you understand. And when you understand, it becomes clear what the right question you need to ask is.

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Beyond listening to them, your job is also to help your prospect understand their pain.

The best closers are less like salespeople and more like therapists. They listen. They care. Then, they ask questions. These questions are designed to help highlight the prospect’s pain and illuminate the solution they need.

This is how you can provide real service and be of help.

However, not all pain is the same. There are three levels that you’ll have to work through in stages. These are:

  1. Ego pain
  2. Intellectual pain
  3. Emotional pain

As you listen to your prospect, they’ll tell you first about their ego pain. To them, this is all that matters.

However, you should know better than this. The only thing that does matter is getting to the emotional pain—but this only ever happens when you ask the right questions.

Asking the Right Questions by Understanding the 3 Levels of Pain

The aim here is to show you how question-based selling works alongside these pain points—and how you can use questions to guide your prospect to what they need.

It takes a good listener to successfully help a prospect.

Ego Pain

This is what your prospect will focus on. As you begin to talk to them about their business, they’ll start to tell you what they think their biggest pain and problem is.

The thing is, what they initially say tends to be nothing but ego pain—surface-level issues that are not the real problems they are facing.

Take this situation as an example:

Prospect: “My Facebook Ads aren’t working. It’s causing me a lot of problems, and I need to fix them as soon as possible.”

This is a problem, but it isn’t their main one. It’s only the first level, and it’s your job to help them see this to get them to the next stage: their intellectual pain.

You: “Okay, I hear you. From the sound of things, your Facebook Ads are broken. I imagine that’s creating some strain on your business. Is it costing you money? What effect is it having on your lead generation?”

Acknowledge what they say so that you’re able to show that you hear them. Then, push them to go deeper.

Intellectual Pain

Whatever their problem is, there’s almost always a level of intellectual pain. Deep down, your prospect knows this. They’re intellectually aware of this pain, but they mask it with their ego.

Why? It’s easier. This sort of pain hits hard and requires them to take real action. As such, they resist it.

However, as important as intellectual pain is, it’s rarely the most important form. It doesn’t get you to the root cause, yet the root cause is where you need to get to.

For this, you need to uncover their emotional pain.

This is where you need to get to—but again, your prospect won’t take you there. It’s your role to listen, reflect, and then continue to ask the right questions.

Prospect: “Yeah, it’s costing me $1,000 per month at the moment. It feels like a complete waste of money. It’s also affecting our revenue because I was expecting it to have at least a 100-200 percent ROI. So as well as it costing me money, it’s having an effect on the money coming in.”

As they tell you about their intellectual pain, listen. Listen so you can understand them and their business.

You: “So as well as this costing you $1,000 per month, it’s costing you $2,000 to $3,000 per month in potential sales. Is that right? I imagine that’s a big strain on you. How does that make you feel? Is it having an effect on you at home? Is this worry stopping you from doing certain things or making other investments?

Dive deeper into what their true pain is. Once you do, the real power of question-based selling kicks in.

Emotional Pain

Welcome to the promised land. Once you get here, you learn about what’s really holding them back.

Prospect: “It’s hard. I feel like I’m doing everything myself, but nothing is working as I want it to. I’m always hustling to make ends meet, and I go home and feel terrible. I’m always under pressure that I can never switch off.”

They begin to let you in, and all you have to do is continue to listen and take it on board.

You: “That must be painful. How long have you felt like this?”

Before long, they start to share certain mindset blocks and limiting beliefs. You begin to understand their true personality. You’ll likely learn things about them that they haven’t told anyone else.

Often, they won’t be aware they feel this way because they’ve never faced it—always pushed it to one side and kept busy with their work.

However, by actively listening and understanding your prospect’s pain, you’re able to uncover what it is they really need and what you can do to help them.

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Wrapping Up

Finding success with question-based selling isn’t just about asking questions. It isn’t about having a script or a list of topics to work from. It isn’t about having an agenda and trying to get your prospect to go down a path you want them to.

Asking questions, after all, is easy. Anyone can do it. The secret is knowing which ones to ask and when.

Remember the points above and take the time to listen so that you can truly help your prospects. Get to the root of their pain by asking the right questions. Otherwise, you’ll only offer a temporary bandage or, worse, you’ll sound like everyone else and lose all their trust.

Be different. Be better. Be the closer who cares.

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Kayvon Kay

Kayvon Kay

Kayvon has over two decades of experience working with high-level closers and perfecting his sales methodologies. He has earned the title of Canada’s #1 pharmaceutical sales representative and continues to share his expertise as a keynote speaker and through his multi-million-dollar coaching program.

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