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.

Examples of business problems include making a fully functional product slightly prettier, slightly decreasing a product’s price, or small work-life balance issues. These are slight annoyances — but aren’t keeping the company from functioning. Business pain points, on the other hand, do.

Pain is the first thing top salespeople look for in their prospects. These are some of the most common business pain points your prospects might face.

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. Process Pain Points

Sometimes there are issues with a business’ systems and processes. Additional pain points, like productivity issues, often stem from process challenges.

Your prospects want to improve internal processes, such as assigning leads to sales reps or nurturing lower-priority leads

3. Financial Pain Points

Many companies overpay for the products and services they use, which results in financial strain. Your offerings might be able to help businesses who want to reduce their spending.

Now that you know which pain points to look for, here are eight questions to help you improve qualifying for business pain.

8 Questions That Can Identify a Customer’s Pain Points

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 on any of these questions, 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 her 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 toilet paper in the bathrooms. 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 toilet paper might lead you to bigger pain points such as, “We don’t have enough toilet paper 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 toilet paper 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.

Not all questions need to be addressed to your prospects. It’s important to take the pulse of the rest of your sales team’s pipelines and challenges and understand what your prospect questions are not uncovering. Here are two questions to ask your fellow salespeople to uncover prospect and customer business pain points.

7. Why are we losing deals?

Pain point question for: Your internal sales team

If you offer more features at a higher cost than Competitor X but are still losing deals to them, you’ve uncovered a business pain point: budget. It’s important to discern whether you need to get better at selling your product, qualifying your leads, or trimming unnecessary features/services from certain plans.

8. Why are customers churning?

Pain point question for: Your internal sales team

Just because you close a deal, doesn’t mean your customer’s pain points go away. Dissect why customers are dropping your business and address those pain points just as you would in the sales process.

If you’re losing business because your customer service wait time is too long — that’s a business pain point for both parties. For your customer, it’s an impediment to them using your product/service to solve for their business. And your company can’t continue to grow in this manner either.

3 Tips for Addressing Business Pain

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. To learn more, check out these sales questions to quickly identify your customers’ needs next.


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