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January 22, 2016 // 6:30 AM

5 Questions to Uncover Business Pain

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Have you 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. 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. So salespeople have to be able to uncover business pain as quickly as possible.

True business pain isn’t a problem whose solution is a nice-to-have. It’s a budgeted, pull-your-hair-out, have-to-get-it-solved, discussed-at-the-board-level kind of problem.

Examples of business problems include making a fully functional product slightly prettier, slightly decreasing a product’s price, or small work-life balance issues. But if your prospects say they have serious 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.

Pain is the first thing top salespeople look for in their prospects. Here are five questions (and three bonus tips!) to help you improve qualifying for business pain.

Five Questions to Qualify for Business Pain

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

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 do you need to solve this problem by?
  • 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.

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2) What is your biggest hairball?

This is a more whimsical version of #1. 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. 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 a more personal version of #1. You’re asking your prospect how the pain affects them personally. 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?

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

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

First, she usually controls the budget for B2B buying decisions. Her pain won’t necessarily be the same as an individual contributor’s pain, but she’s the one that needs to pull the trigger on a purchase, so start with her pain.

Second, 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.

Third, 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?

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?

As mentioned above, business pain isn’t two employees complaining that 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.

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.

How do you qualify for business pain? Let us know in the comments below.

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