Five Must-Ask Questions to Discover Your B2B Prospect’s Pain Points

Article by | May 22, 2020 Positioning and Messaging

The Article in 60 Seconds

If you don’t know what your prospective customers are thinking, feeling, and doing about the issues they are facing, you don’t know your customer.

They are on a self-service journey, making irrational decisions, and trying to navigate the confusion caused by conflicting information from multiple solution providers.

In this blog post, we:

  • Present a video about the cognitive triangle
  • Outline types of pain points your prospects experience
  • Suggest five questions you can ask prospects through the sales process

Think About This

  • B2B customers travel the majority of the way through decision-making process before ever engaging a sales representative. [Multiple Sources including CEB, LinkedIn, and Forbes. Plus a rebuttal.]
  • B2B customers are 70% more likely to say a growth purchase requires significant organizational change compared to a repurchase decision. And even those who are motivated face an uphill battle. [2019 Gartner Account Growth Buyer Survey]
  • The group of decision-makers at a B2B company spends at least 15% of the buying cycle time reconciling and prioritizing conflicting information. [Gartner]
  • Developing a 360-degree written persona can grow revenue. Organizations that do exceed their goals by 2.2 times. [Cintell]
  • Don’t forget those searching in anonymous windows — 71% not allowing you to track them through your funnel. [DemandGen Report]

The Cognitive and Rhetorical Triangles

For a transcript of the video, click here.

We all have pain points in both our personal and professional lives. They are what can drive us insane, and therefore, drive our choices and purchases.

Whose Pain Is It?

Understanding your customer’s pain points can be just as annoying to you as the pain points are to your customers.

The questions your customers wrestle with cause them to feel at risk in their careers. The pain points make them frustrated. They are worried that if they don’t overcome them, they will be held responsible for limiting their companies’ growth. These issues are discussed over and over again.

Types of Pain Points

Pain points typically fall into three categories:

Process/Productivity Pain Points

Particular processes take too long, which inhibits productivity. Current solutions waste too much time with minimal results. For companies seeking a new technology solution, this is the most common pain point. For example, the B2B tech company known as PandaDoc speaks to this particular pain point well, as their product can slash the amount of time it takes to create sales proposals (among a slew of other cool features.)

Panda Doc Marketing

Financial Pain Points

In some cases, your prospective customers might be spending too much money on their current solutions and they are either looking to save money, or get a better bang for their buck. You’ll want to find out early on in the conversation what your prospect is willing to spend, as this will be a key qualifier (or disqualifier) for future conversations. BlueSnap, an all-in-one payments platform sold to B2B and B2C companies, addresses the financial pain point throughout their marketing and sales process.

Bluesnap website

Functionality and Support Pain Points

Your prospective client thought they had found the ideal solution to address their pain points… until it was implemented. When a company purchases the wrong software they hit functionality and support hurdles that lead them to seek out a new provider quickly.

The belle of the ball answering this pain point is Zoom. Pre-COVID, they spoke to this pain point by concentrating on client testimonials and reviews as a direct response to the struggles potential users had with their competition. It’s an understatement to say that it worked.


zoom reviews


Zoom Current

Why do Pain Points Matter?

Pain points help B2B technology companies speak to their prospects like humans. Rather than trying to simply sell a product, when you understand your prospect’s biggest pain points, you can offer a solution just for them.

Understanding your buyers’ pain points can help you:

Determine if a prospect is the right fit

Speak to prospects on a human and emotional level

Close more deals

Rather than rattling off a list of features, address their problems. Ask questions to draw out the situations that are most painful to them. Then guide them to how your product or service alleviates that pain. Your conversation becomes more meaningful and convincing, and prospects can often make decisions more quickly when told something can eliminate their company or department’s biggest pain.

Types of Questions to Ask

In general, your sales (and/or marketing team) should ask two types of questions to uncover a prospect’s pain point.

Open-Ended Questions

Questions should start with who, what, where, when, why, how, help me, and describe.

Probing/Clarifying Questions

Generate a story with your questions.

Tell me about…

When that happened what did you do? How did you feel?

(If you want to learn more about probing questions, HubSpot provides a list of 100 probing questions.)

It is important to note that you should avoid leading questions like, “Do you think your team could benefit from a better project management software?” Leading questions often result in a simple “yes” or “no” answer, when you want your prospect to dish the details.

5 Must-Ask, Open-Ended Questions to Uncover Your Prospect’s Pain Points

There are dozens (or maybe even hundreds) of questions that you can ask a prospective customer to uncover their pain points. But in most cases, a call in your first encounter with a prospect will last less than an hour — and it’s on this call where determining pain points is key.

1. What is the biggest challenge your team/company is currently facing?

Categorize their answer as financial, process-driven, or support-driven.

Good follow-up questions include:

  • Can you provide an example?
  • What have you already done to address this?
  • What happens if this problem goes unresolved?

2. What takes up the most time in your day?

Good follow-up questions include:

  • Can you quantify the cost of your inhibited productivity?
  • How many hours do you think you lose on a daily/weekly/monthly basis?

3. What does your boss care most about?

Good follow-up questions include:

  • How would solving this problem help your boss?
  • Can you be more specific or provide an example?
  • What is the cost to your boss right now by not having this problem solved?

Screen Shot 2020-04-08 at 10.43.04 AM

4. What has prevented you from solving this problem in the past?

In most cases, problems don’t creep up overnight.

Good follow-up questions to ask include:

  • Where did the problem start?
  • Ideally, when would you want the problem fixed by?
  • If you tried solving this problem in the past, how/why/when did it fail?

5. How do you think a new product would solve the problem?

Setting and managing expectations is an important part of the sales process.

Some good follow up questions to ask here include:

  • What is your timeline for getting this problem fixed?
  • Who in your organization needs the problem fixed?

The First Thing to Do After Reading This Article

Think about a recently-closed deal. How well do you know the pain that led them to sign with you? Answer the questions yourself then place a call to your point of contact and have a candid conversation. How far off the mark were you? Let that experience guide how you adapt your content and your sales process.

Video Transcript

Mark Whitlock (00:01): Hi, I’m Mark Whitlock. Thanks for taking a few minutes to watch this video from Golden Spiral where we “Shape Technology Marketing” and help you own your market. We’re a B2B tech marketing company. If you found us on YouTube, will you look in the description of the video and click over to our website? There you’ll find a helpful article on the five questions every B2B tech company needs to be asking their potential customers through the marketing and sales process. and if you’re on our website and watching this video, be sure to read the article into which this video is embedded. On today’s video, we’re going to talk about two different triangles now they are very similar in how we look at them, but we’re going to look at how your company needs to look at your customer and how your customer is looking at your company and a couple of things to be aware of before then.

Mark Whitlock (00:51): It’s a much discussed statistic, but more than half of your customers are getting deep, deep, deep into the funnel before they even talk to a sales representative, before you even know they’re on the radar screen. And recent statistics show that 57% of your shoppers, the folks looking for your solution in a B2B context, are doing so anonymously. They’re using incognito windows and they are not leaving information behind. So you can’t even follow the breadcrumbs to be able to offer them more information. That’s why it’s so important for you to understand your customer at golden spiral. We talk about the Buyer Matrix. This is our proprietary methodology for helping a client understand who their customer is and we’ve seen time and time again how our clients have had these great epiphanies. We’ve watched CEOs and CEOs and CMOs get wide eyed with a greater understanding of their customer than they’ve ever had before.

Mark Whitlock (01:56): And what I’m going to show you is just a small part of the thought process we go through. So let’s look first at how you need to think about your customer. And I call this the cognitive triangle. Now you’ve probably seen this idea in many places. It’s a common psychological tool to use, but we’re going to use it in the context of what we’re trying to accomplish. And again, it’s a triangle. We’ll call the cognitive triangle. You need to understand how your potential customers think, feel, and what they do. Now, why is this important? It’s important because not all of your customers have the same personality type. It’s basic.

Mark Whitlock (02:39): You’re going to have those who were very cerebral, those who think process first, and they’re going to be thinking about things. Here’s something for you to consider. Uh, they’re looking at customer service, say, and these folks may look at the, the numbers and the, and, and the KPIs that are available and go, “Our customers are not being served fast enough. Too many seconds are elapsing off the clock between the time that they call or the time that they open a chat window until the time that their problem is solved.” And so that may be how they’re thinking about the problem they want a tech solution to solve.

Mark Whitlock (03:15): But you’ve got other people in your organization, you know who they are. These are people that feel first, these are the drivers, these are the artists among your team and among your leadership. And they may look at the situation and go, “We’re not serving our customers well. We’re just not doing it.” They’re coming at it from a completely different point of view. Now what you want is you want those who were thinking to inform those who feel and those who feel to inform those who think, but here’s why I’m talking about this right now because those that take that thinking approach are going to research and shop completely differently than those who feel. You’re going to have two completely different experiences in the process.

Mark Whitlock (04:01): So let me give you this idea. Here are the things you need to understand when it comes to the cognitive triangle. You need to understand what is my potential customer thinking, feeling, and doing now in light of their problem? What are their thinking, feeling and doing right now and then here comes your product after your product is installed, after you have onboarded them after they’ve been able to use it and see the benefits of it, what are they thinking, feeling and doing at that point? If you have that well-rounded, of an understanding of where your clients and potential customers are coming from, that’s going to help you a long way into what you’re doing. Now. That’s how you need to be thinking about your customer. Now let’s talk for a second about how your customer is approaching you, and I’m going to call this the Aristotle triangle.

Mark Whitlock (05:03): And again, this isn’t anything new. This has been around since the Greek days and since this Greek, we’re going to use some Greek language. Your customers are looking at you and they’re looking for three things. They’re looking at your logos, they’re looking at your pathos, and they’re looking at your ethos. What does that mean? Well, when you think about logos, we’re talking about words, we’re talking about words, we’re talking about logic, and so as you’re going through this process, you’re wanting to answer the question why they are asking you why? Why does this solution meet our needs? Why do I have this problem? Why does that work in this situation? They’re asking why, and you’re going to fill in that information through your content, through your videos and podcasts and social, your blog articles, through your live events and webinars. If there are live events through your Zoom calls, you’re going to deliver this information through your content.

Mark Whitlock (06:08): Let’s talk about pathos. Pathos is emotion. But what we’re talking about in the context of your customer looking at you is your values. You’re looking at how are, how are you going to be a good partner with those that you’re working with? The question this asks answers is, so what? So what? What? Why should I work with you? What so what? So what? What does it mean? What? What difference is it going to make? You know, you’ve seen the statistics, you’ve read the articles as the number of buyers increases and the age of those buyers decreases. They’re looking for companies that not only provide a solution, but whose values match theirs. They want a partner, not just a goods and services supplier. So you’re answering, so what this comes through your about us page, your pricing page. When they see your company’s personality come through your website. That’s what matters.

Mark Whitlock (07:11): And then lastly, both of these, the content on your website and the other pages on your website are driving them to the most important point, part ethos. This is ethics. This is your credibility that is demonstrated in your endorsements and in your testimonials. That’s why those are so important. And the question you’re answering here is why. And you can enter the name of your company right there. Why you? Why this solution? Are they going to be a good partner? Do their values line up with ours and why them? So, again, there are a lot of similarities between these, but this is how you need to be thinking about your customer. What are they thinking, feeling, and doing now? And once your product’s installed, what are they gonna be thinking, feeling and doing? And then as your customer is researching you, are you answering their why questions with your content? Are you answering their, so what questions with other pages on your website to demonstrate who you are and what you believe and what you stand for and can they trust you? Do your endorsements and testimonials tell the story that you’re to be trusted and that making the massive change in their company, that’s going to have to come about if they install your product, it’s worth it and you’re going to be a valued partner.

Mark Whitlock (08:43): So thanks for watching this video. If you like this content, we encourage you to subscribe to our weekly newsletter called The Angle. So on any page on golden spiral with the bottom of that page, you can click on subscribe to The Angle. And if you love podcasts, Studio CMO is a podcast we’ve designed for marketing executives. We do two things on that podcast. One, we tell the stories of marketing executives and how they got from one place to another. What’s their background, what’s their story, what’s the journey? And the second thing we break down their marketing successes and take a look at them strategically and tactically so that you can implement some of their big wins where you are. So come join us if you would subscribe to the angle or subscribe to the podcast Studio CMO. And again, if you’re seeing this on YouTube, click through to our website to read the article. And if you’re on our page, go ahead and read the article about the five questions. Every B2B tech company needs to be asking their clients and the process of the marketing and sales funnel from Golden Spiral. I’m Mark Whitlock.

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