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8 Questions to Ask a Potential Customer About Their Business Pain Points

By November 19, 2020November 21st, 2020No Comments

Guest Post By  Dan Tyre

Ever spent time with a prospect who didn’t buy? Of course you have.

Is it fun?

No, it is not.

Selling to people who can’t or won’t buy is a huge drain on your sales productivity, budget, and team. Top two-percenters need to spend time only with prospects who need your help, want your help, and are willing to work with you to solve their problems.

Your prospects need to have authority and money, but having business pain trumps both. If your prospects don’t have business pain, they have no need. And without need, there’s no hope for a sale. It’s up to salespeople to ask effective sales questions and uncover business pain as quickly as possible.

Business pain points keep the company from functioning and, therefore, should be addressed as a priority.

Business Pain Point Examples

If your prospects say they’re experiencing employee dissatisfaction and retention issues that are impacting their productivity and hiring, customer churn that impacts their revenue, or a severe lack of leads that makes it impossible to hit their revenue goals, you’ve hit on business pain points.

Pain is the first thing top salespeople look for in their prospects because pain is what starts them on a buying journey in the first place and is the driving urgency to find a solution. These are some of the most common types of business pain points your prospects might face and examples of each:

1. Positioning Pain Points

What company doesn’t need to acquire more or better business? However, this end goal is easier to set than to achieve. Many businesses may understand — or think they understand — what’s holding their marketing and positioning efforts back. Here are some examples of what you might hear from prospects who have positioning pains:

  • “No one knows who our company is.”
  • “Our competitors are outspending us.”
  • “The market is changing, leaving us behind.”
  • “Until now, we haven’t considered digital marketing, so we’re behind.”

Because acquisition is so closely aligned with revenue, successfully identifying a positioning pain and your solution for it is a great way to prove value.

1. Productivity Pain Points

Is there something that’s prohibiting a company and its employees from working efficiently and effectively? Your product or service might be able to help them solve these issues.

2. Financial Pain Points

Money is a big topic in business, and many business pains are caused by lack of it and solved by more of it. Every company benefits from improving their financial standing. Here are some examples of critical financial pain points that require serious solutions:

  • “We’re not selling enough to keep the lights on.”
  • “Revenue is up, but profitability is low.”
  • “We don’t have enough visibility to know if we’re making good financial decisions.”
  • “We may be overpaying for equipment and tools, but we don’t know what to cut.”

Your offerings might help businesses who want to reduce spending or better manage cash flow.

3. People Pain Points

People are at the heart of every business, often constituting both the greatest expense and largest asset. If there are people problems such as the following, it can cause problems in other areas of the business:

  • “Employee morale is low.”
  • “We lose our best employees to higher paying positions elsewhere.”
  • “Our lack of diversity leads to lack of innovation.”
  • “We can’t trust our middle managers to train and motivate.”

If your product or service helps organizations manage, incentivize, or delight employees, you’ll take the pressure off those at the top and look like a hero to anyone else involved too.

4. Process Pain Points

With people problems come operational problems (or maybe the other way around). Your prospects know that the best way to achieve repeatable success is by implementing repeatable processes. The question, then, is “how?” They may be facing hurdles such as:

  • “Our hiring process is unwieldy, and we struggle with finding highly qualified candidates.”
  • “Customer churn is high because our service department is inundated and can’t keep up.”
  • “We have no system in place to qualify leads.”
  • “There’s inconsistencies in each employee’s workflow, which leads to disorganization and varying performance.”

If you unearth process pain points, ask your prospect to envision what a smoothly running company, department, or system would feel like and what kind of difference it would make.

5. Productivity Pain Points

It’s the job of managers to remove roadblocks for the team so that things get done, productivity is high, and profit benefits. That said, it’s easy to get stuck in the weeds of the business and fall victim to inefficiencies that waste major time. Here are some examples of productivity pain points in business:

  • “We keep missing client deadlines.”
  • “We spend way too much time in meetings.”
  • “Our administrative work is out of hand.”
  • “Quality issues with our product has led to costly recalls and/or customer churn.”

If there’s something prohibiting a company and its employees from working efficiently and effectively, you can position your solution as a time, money, and headache saver.

8 Questions That Can Identify a Customer’s Pain Points

As you’re performing sales qualification with a prospect, here are eight questions to help you unearth some of the business pains that can create great dialogue:

1. What’s your biggest inhibitor to company (or division) growth?

Pain point question for: All prospects

This is a classic soundbite that cuts straight to the heart of the matter. Every company is in the business of growth, so the biggest obstacle to growth is generally a serious pain.

Many prospects haven’t thought about this at all, so this question builds your personal credibility as well. Helping prospects talk through their current business situation can increase your understanding of the company while demonstrating your expertise in a non-showy way.

Usually, the business pains fall around revenue, customers, employees, product, or investment capital. Get to the meat of the conversation quickly with these follow-up questions:

  • What’s your plan to tackle X pain?
  • When is your deadline to solve this problem?
  • Do you think it’ll be easy or hard to solve it?
  • Who in your company is working to fix this right now?

These questions will blow your conversation wide open. By drilling down their responses to any of these, you’ll learn a lot about your prospect’s pain and spot opportunities to help.

You will also learn how they are approaching their pain. You should hear a certain amount of stress in their voice. This is healthy. It means they are likely to spend money to help address a business issue.

2. What is your biggest hairball?

Pain point question for: All prospects

This is a more whimsical version of question one. I like using it because it has personality, is funny, and creates a vision of chaos.

Most importantly, it’ll stir up your prospect’s emotion and gets to their core needs.

Whether they’re facing a major cross-departmental operational issue, an internal team problem, or a clear obstacle to growth, getting your prospect talking about what they’re most frustrated by is a great way to get them excited about a potential solution.

It is also more personal. You’re asking your prospect how the pain affects them. Based on their answer, you’ll be able to determine if they have a potential personal win that can give you some extra support to get the deal through.

3. What does your boss obsess about?

Pain point question for: Individual contributors

You won’t always be talking to the head honcho — sometimes, you’ll be speaking to someone two or three levels below them.

It’s in your best interest to get them involved in the conversation as early as possible. There are three reasons for this.

  1. They usually control the budget for B2B buying decisions. Their pain won’t necessarily be the same as an individual contributor’s pain, but they’re the one that needs to pull the trigger on a purchase, so start with the decision maker’s pain.
  2. A manager’s pain usually filters down to her direct reports. While an individual contributor and manager won’t view the problem the same way, a win for the manager will usually improve her direct reports’ lives as well. A lot of your prospects will have crappy bosses, and getting them off your prospects’ backs is a big motivator in the sales process.
  3. It signals inexperience. If your contact doesn’t know (or think about) their boss’s business pain, then it might be a sign that they’re too junior or inexperienced to help move a deal forward.


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

Pain point question for: Individual contributors and managers

This is another angle to approach business pain that focuses on your point of contact.

Salespeople hear over and over again that buyers care more about value than features, and this question reveals the concrete value your product could have to your prospects on a personal level.

Ask your prospect about how solving a business pain would impact their team. Would it save them two hours of work a day? Cut their time spent in meetings in half? If you can find something concrete your prospect’s itching for, dig deeper and see exactly how you can help.

5. What’s been repeatedly discussed at standups or all-company meetings by senior management?

Pain point question for: Senior managers and leadership

As mentioned above, business pain isn’t two employees complaining there isn’t enough coffee in the break room. It’s not something that can be fixed quickly or easily.

Pain is what keeps the CEO up at night. It has to be addressed for the company to continue operating at full speed.

What do senior managers put on their quarterly planning agendas? What do they talk about incessantly? What do they send all-company emails about? This is the business pain you’re looking for.

6. What are your gripes?

Pain point question for: All prospects

This might seem petty, but the responses you’ll earn with this question can be extremely telling.

What begins as a complaint about not enough coffee might lead you to bigger pain points such as, “We don’t have enough coffee because our company-wide budgets have been slashed this quarter. We’re really focusing all available resources on advertising in the coming weeks and months.

A lack of coffee is a seemingly laughable and lighthearted gripe — but when the experienced salesperson asks follow-up questions and digs in here, it can illuminate a larger issue you have the resources to solve for.

7. Why are you losing deals?

Pain point question for: Individual contributors and managers

Asking this question might uncover positioning pains, process pains, or productivity pains in one of a company’s most important departments: the sales department.

If you can position your product or service as something that enables sales or marketing teams to acquire more business, you can win over those bottom-line-focused decision makers.

8. Why are customers churning?

Pain point question for: Individual contributors and managers

Losing customers is a big pain, and it can be caused by any number of issues that you may have a solution for.

This is another question that can give you really good insight into how their business operates, what challenges they may be facing, and what kinks in the chain may be prohibiting growth. Information about any one of these can open up a conversation about how you can help.

3 Tips for Addressing Business Pain

Once you identify pain, you can determine how to solve it for your prospect. This is an incredible tool to leverage as a salesperson since you can become a solution-provider rather than a product-seller. Here are three tips to start positioning in this way:

1. Use your prospect’s language when talking about pain.

This is a psychological technique that can go a long way in building trust with your prospect. Instead of trying to appear impressive by relying on jargon only your colleagues would understand, show your prospect you take them seriously by using their language and terminology.

2. Find out who’s empowered to solve the pain.

Find the economic buyer as quickly as possible. Ask your prospect whose budget a purchase would come out of and what teams would need to be involved in a buying decision. There’s little point spending hours with a person who can’t ink a deal.

3. Identify additional key stakeholders as early as possible.

If you’re selling to multiple teams and one team has completely different priorities than another, you need to know early. If you’ll have to go through a two-month legal review process before you can close a deal, you need to know early.

Prospects are sometimes worried they’ll appear less authoritative if they tell you they’re not the sole decision maker, so I like to use the following questions to avoid that impression:

  • Who besides yourself needs to be involved in this decision?
  • Who else would want to know that we had this conversation?

Affirm your prospect’s involvement while asking for information, and it’ll be easier to make sure your pitch meets everybody’s requirements.

Inbound sales is all about empathy. To close more deals and become as helpful as possible, start asking the right questions to the right prospects.

Guest Post By  Dan Tyre

Dan Tyre is sales director at HubSpot. Dan is a senior level software executive, advisory & governance board member with extensive experience in hyper-growth environments from start-up to $1B+ sales. Skilled at inbound marketing, inbound sales, inbound service & building a culture of personal responsibility and achievement. My goal for the next 30 years is to do the most good in the universe.

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