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How to Identify Customer Pain Points (Examples & Tips)
Shawn Casemore - Accelerate Sales Growth Shawn Casemore - Accelerate Sales Growth
For Immediate Release:
Dateline: Toronto, Ontario
Tuesday, September 19, 2023


Knowing how to identify customer pain points contributes to faster sales conversions.

Nothing, absolutely nothing in sales converts better or faster than uncovering (really even just finding) your buyer’s pain points.

In this post, we’re going to reveal some strategies you can use to uncover those pain points, and I’ll even throw in a bonus that explains what to do when you find them.

When it comes to sales, you need to uncover your buyer’s objectives. That’s pretty straightforward, right?

  • What are your objectives for making this investment?
  • What is it that’s driving you to want to make this decision?

But there are a few things you need to add into your discovery questions or into your discovery process to make sure you pull out your customer’s specific pain points.

Explanation of “Customer Pain Points” Meaning

Now, the reason it’s called customer pain points is because it has to have some sort of a personalized impact on the buyer.
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Let me say that again.

Pain point, although that term is thrown around a lot in sales, really suggests that you need to uncover the specific reasons why the sale is important to your buyer. And if the sale doesn’t happen, what’s the impact on them? That’s what a pain point really is.

So I don’t want you walking around saying, “Hey, so tell me about your pain points”, because they’ll have no idea. Your buyer will have no idea what you’re talking about.

How to Identify Customer Pain Points (4 Tips With Examples)

identify customer pain points

Here’s the first thing I want you to consider when it comes to your discovery process and your discovery questions. Step one, ask impact questions.

1. Ask Impact Questions

Now, here’s what I mean by this:

When it comes to understanding how your product or service will fit or will help or will support your buyer, you need to understand what is the impact it will have on the company. (And obviously on the buyer themselves. We’ll get to that in a minute.)

So when you’re asking discovery questions, make sure you include a question that asks about impact.

Here’s an example:

Let’s say for a moment you’re selling insurance. You might say, after they’ve talked about the coverage necessary and the term and maybe the challenges they’ve had with other insurance carriers in the past, you could say,

  • ”Okay, so it sounds like if we can put together a policy that covers X and Y and meet your budget criteria, this will work for you.
  • But let me ask you a question.
  • If we can make this coverage and put it in play and we can meet your budget criteria and we can make sure we’re 24×7 responsive for your needs, what would the impact be on your company here?
  • Or, what would the impact be for you personally?”

Impact questions help us identify customer pain points –
the reasons and more so the benefits our buyer will receive with our product or with our service.

Let’s build on that idea of impact questions for a minute.

Pain comes down to, as I mentioned, understanding your buyer and what matters to them, what’s causing them frustration. And that’s going to differ depending on

  • the buyer,
  • their role,
  • the position,
  • what you’re selling,
  • all these various factors.

2. Always Understand the Personalization of Customer Pain Points

discover what is causing customer frustration

But we really need to, and this is point number two, personalize the pain points.

What we do with the impact questions is we go from what’s the impact in your company to what’s the impact on you?

But now I want you to think about personalizing the entire discovery session around your buyer.

You always have in the back of your mind, “I really have to understand how this helps my buyer” as you’re asking your questions:

  • What kind of product or service are you using today?
  • Who are you buying this from?
  • Are you happy with what you’re receiving?
  • What would make this better for you?
  • How could we improve your service?

And so on.

Let me give you an example of this and why this is important:

Let’s say you’re selling a piece of furniture to a company and the person you talk to in the company is the dealer. You decide together that they’re going to move ahead and make a buy, so they connect you with procurement (or with supply chain or with purchasing).

Now purchasing calls you and says, “Here’s what I want from you”:

  • I want it cheaper.
  • I want more quantity.
  • I want better quality.

Whatever the case is, you really have to understand that whatever your buyer told you that was important to them now adjusts a bit because now your buy is moving through somebody else.

So you have to uncover, you almost have to revisit discovery when the buyer changes, which is often when procurement steps in. You have to start to personalize and understand how you can support procurement.

personalize pain points for every buyer

Keep in mind that anybody in supply chain or procurement involved in a transaction, such as the example I’m sharing, is really looking for what’s in it for them. And the way you’re going to not only make the sale but build a long-term relationship is to help them.

Oftentimes, sales professionals tend to dig in deep with their buyer. Maybe it’s the dealer themselves, but then they get turned over to procurement. They’re like, “oh my gosh, this is so painful”!

Well, that procurement person or purchasing person, they’re a person too, and you really got to build a rapport relationship with them. (No different than your dealer buyer in this example.)

When you are moving through discovery and when you’re trying to understand not only the impact, but how your product or service will fit, always be thinking about personalization regardless of who you’re talking to.

Anybody that gets brought into the discovery process is somebody that you have to understand what’s important to them and how interacting with you will benefit them. Once you understand how it might benefit them, you can turn that around and use that as part of your sales process.

3. More Questions to Uncover Customer Pain Points in Sales: Go “3 ’Whys’ Deep”

probing questions go 3 'whys' deep

This next strategy I want you to use when identifying customer pain points. The name is a little bit funny, but I think it’ll make sense to you in a minute. I call it the “3 ‘Why’ Deep”.

Here’s what I mean:

When it comes to asking questions and understanding pain points of your buyer, the only way to really understand what’s behind the need, what’s behind that desire to possibly buy from you is to ask ‘why’.

But the problem is a simple ‘why’ will often get us a surface answer, and we need to go a little bit deeper. Think about it like peeling back an onion.

So here’s an example:

I’m selling you an investment of some kind, okay?

  • We’ve discussed the investment.
  • We’ve discussed the returns on the investment,
  • How it’s performed in the marketplace,
  • How it’s going to meet your objectives.
  • It’s not too risky.

All of those things that you discuss when you’re selling financial products.

And then I say to you, let me ask you a question:

  • Why does it make sense for you to be talking to me about investments right now?”

They’re probably going to tell you,

  • “I’m not happy with the performance of my current investments”, or
  • “I’m upset with my current advisor.”
  • “It’s just not working out.”

Okay, so there’s “Why #1”.

So when they respond, here’s “Why #2” might be:

  • “You’re talking to me right now because you haven’t seen the performance you’re looking for. Why is better investment performance something that’s important to you right now?”

I simply take their answer and I turn it into a why question. Why? (Pardon the pun.) It’s because I’m trying to understand; trying to go a little bit deeper.

The old saying goes that people often know what they want, but not necessarily what they need.

So we need to peel back the onion. We need to peel back the layers and ask them why questions to really understand what’s behind that.

In this particular example, “Why #1” was understanding why they’re talking to me now, why is now the right time?

And then when they give me a response, I simply ask them ‘Why’ that’s something that’s important right now. So in our example, they say, well, returns aren’t what I’m looking for. And you say, okay, “Why are stronger returns important for you?”

And then they might say something like “Well, because I’m planning to retire in a couple of years.”

  • “So, interesting. Why wouldn’t you move ahead with this solution based on what you’ve just told me?”

turn a question into a conversion

You see that a little bit of a U-turn there at the end, right? A little tricky.

So the first ‘Why’ that I want you to ask is really just trying to understand:

  • Why are they meeting with you now?
  • Why is this important now?
  • Why did they agree to the meeting?

I’ve just given you three ways to say this.

The second ‘Why’, depending on what they respond with an answer, I want you to turn that around into a why question, because I’m trying to understand, again, their primary objectives here.

When they give you the final answer, I want you to turn that around on them.

So, in our example where the final answer was, well, I’m thinking of retiring in a few years. Then you’re turning this around to take that question and flip it on them. That’s the third (BONUS!) stage in the “3 Whys Deep”:

  • Why wouldn’t you move ahead?

See what I did there? So I’m moving the buyer from the initial, “I have a concern” to I’m almost trying to convert you.

Customer pain points require that we peel back and understand what’s behind them, but we always want to take that opportunity and try and convert the sale whenever possible.

If you’re a high performing sales professional, I found that there’s one tool you use that non-high-performing sales professionals or underperforming sales professionals don’t use, and that is some sort of planner that guides your activities, your goals, your objectives on a daily, weekly, monthly basis.

To try and help you in this regard, I created a simple resource. You’ll see a link here – I call it the 30-Day Sales Action Planner. It’s meant to help you set out your goals and targets and to plan those out for the next 30 days. So I encourage you to click the link and grab your copy. There’s no obligation or cost. It’s my gift to you to try and help you continue to grow as a sales professional.

Let’s go on to the last tip.

4. Consider Your Customer’s Emotional Investment

This last point is pretty straightforward. When it comes to sales and selling, we’ve got to think about emotions as well as logic.

Too many sales professionals, especially if you’re selling technical products, maybe you’re selling software, MSP services, engineering services, accounting services.

We think from a technical standpoint, so when we’re talking to somebody, if they’ve agreed to talk to us, we think they need our technical help, our technical expertise.

They probably do, otherwise they wouldn’t speak to you.

consider your customer's emotional investment

However, there’s always an emotional side to everything.

So if you’re dealing with small businesses, for example, and you’re talking to the owner when they’re speaking to you and considering your product or service, they’re really balancing the money they invest with you versus the money they keep in the bank for the business or the money they take maybe as a dividend to take a vacation this year. It’s very, very personal.

So we’ve always got to think about the emotional side of what we do.

Now, in a bigger corporation, you might say, well, employees aren’t attached to money the same. So if you’re dealing with a VP and a bigger corporation, what’s important to them? It’s probably looking good in front of their peers. Maybe it’s to get the next promotion.

When we consider the emotional side of any interaction that we have, it brings up different kinds of questions. I’ve shared a few with you here today.

I always want you to think it’s not just information and logic that’s going to get people to engage with me. I’ve really got to engage with them on an emotional level:

  • We smile a lot.
  • We ask some personal questions, not at awkward times, by the way, but we get to know them a bit.
  • We build some rapport.
  • If they’re telling us about something that’s stressing them out, we sit and we listen.
  • We acknowledge.
  • We empathize.

Keep in mind that logic is important. Information is important, but emotion is critical if you want to make the sale.

Now, if you are looking for more insights on how to be a top performing sales professional, make sure you watch my video on how to ask good sales questions where I give you some additional skills you can apply when it comes to understanding the pain points of your buyers.

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© Shawn Casemore 2023. All Rights Reserved.

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Name: Shawn Casemore
Title: President
Group: Casemore and Co Incorporated
Dateline: Chatsworth, ON Canada
Direct Phone: (519) 379-7697
Main Phone: (519) 379-7697
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