How to Uncover Pain Points: It’s All About Asking the Right Questions

hen talking to a prospect – it all comes down to asking the right questions. Your prospects most likely started their buying journey in the first place based on a business pain, and now they’re looking for a solution.

The best way to uncover this business pain is by getting the prospect talking. And what’s the best way to do this?

By asking open-ended questions.

Avoid questions with yes or no answers – this will only give you a narrow and limited view of your prospect’s problems.

The key is to ask open-ended qualitative questions that require an in-depth explanation, giving you a broader view of the problem. This allows you to grasp as much information as possible.

Here are some questions you can ask to uncover your prospect’s pain points:

What takes up the most time in your day?

Why isn’t your current solution and/or process working for you?

What is the biggest challenge you’re currently facing?

You mentioned frustration around X. Can you elaborate?

What is preventing you from hitting your goals?

What’s the main thing you would say is holding your business back from growth?

If you had an unlimited budget, what is the first improvement you would make?

What is one thing you would change about the current operations of your business and/or team?

In the questions above, your role is to carefully listen and pinpoint the issues that your solution specifically can solve. And when you present your solution, your response should be tailored around what the prospect said.

This way, it shows you were actively listening as well as addresses the prospect’s pain point head-on.

Always make sure to rephrase what the prospect said to make this clear, for example: “X will help save you hours per day” vs. “You mentioned you waste hours per day logging information, well X will reduce that by Y.”

Tip: In the questions above, incorporate the name of your prospect’s company and specific references based on the research you did before the call – that way your question is more direct and shows you’re not reading off a script, you’re asking the question for them.

Validate Your Solution With Social Proof

Just because you’re saying you can solve your prospects pain points, doesn’t mean you can – they need proof.

This is where customer testimonials or use cases can come into play. For both sales and marketing, this is crucial for targeting customer pain points. You’re giving your prospects a chance to hear from real people.

The key here is to make these use cases as genuine as possible.

Start with a Prepared Question

First, a good salesperson does their homework by researching the prospect before the sales meeting. From that research, you can formulate a well thought out, open-ended question to kick off the sales meeting.

Whether you are prepared with an open-ended question or need to ask a generic opening question, the importance of that introductory question is two-fold. First, it sets the course for the meeting by leading the prospect where you want to go in order to discuss your product or solution. Second, it helps you maintain control of the dialogue throughout the meeting.

Conversely, you should not start with a direct, qualifying question. That is too early in the meeting to begin discussing potential products or solutions. You need to take the time to listen and learn from the prospect’s positioning.

A top performing salesperson will anticipate what type of answers the prospect will provide to your prepared introductory questions. That way, you can remain in control of the dialogue without stumbling around trying to figure out an answer, losing the audience.

This will lead you to the next type of questions you should be asking to unlock the prospect’s pain points.

The Importance of Clarifying Questions

Top sales reps know that the key to a successful discovery call is centering the conversation around the prospect, their pain points, and how your solution will help them – this is done by asking questions.

But are you asking your prospects the right questions?

You want to avoid all questions that can be answered with a “yes” or a “no.” Your goal is to ask open-ended sales questions that involve in-depth explanations so you can grasp as much information as possible to tailor your sales pitch around them.

You Must Get Prospects Talking

Use open-ended sales questions to get prospects talking and bringing the conversation to more of a discussion than a Q&A.

Based on their responses, ask questions accordingly. Don’t be a robot, make the call as conversational as possible. Listen, ask questions about what they’re saying, rephrase what they say, and make it clear that you’re listening.

Remember – getting your prospects to talk is a win-win. It not only helps you better understand your prospect but will increase the likelihood that the prospect looks back on the conversation in a positive light because everyone likes talking about themself.

Let’s face it, you wouldn’t want your doctor to provide treatment without first giving an examination. And you wouldn’t want your mechanic replacing parts before taking a look under the hood. The same goes when it comes to the sales process. If you want your product or service to be the solution, you first must have a thorough understanding for the problem and all of it’s implications. Insight is key. If your goal is to convert a prospect into a revenue-generating customer – make sure you understand their pains.

Ask insightful questions It is important that your sales team is asking questions that get prospects to open up about areas of frustration. Rather than dominating the conversation with product pitches and sales speak, turn the conversation on them by asking insightful questions that give you valuable details. For example, here are some questions that can help dig deeper into a prospect’s pain points.

Now that you have a general overview of the prospect’s positioning, you can start drilling in deeper based on the prospect’s answer. This includes asking clarifying questions.

Clarifying questions shows that you did your research on the prospect before the meeting. Or, if you were not able to do research, it shows that you are capable of thinking on your feet to maintain control of the meeting.

Examples of open-ended qualifying questions that you should complete with relevant and specific details include:

  • Can you tell me more about…?
  • Can you explain why your company does…?
  • Would you elaborate on why…?
  • Who in your organization needs the problem fixed?
  • What does the problem cost your business?
  • Where did the problem start?
  • When does the problem need to be fixed by?
  • Why has it not been addressed yet?
  • How have others tried to fix the problem in the past?

Now you’re getting closer to the prospect’s pain points by gaining a better understanding of what opportunity they are trying to capitalize on or what concern they need to address.

The top 5 concerns ranked by homebuyers are:

  1. Not able to find a home I like within my budget
  2. Not saving enough for a down payment
  3. Difficulty paying the monthly mortgage
  4. Can’t find a house I want to buy
  5. Home prices falling after I buy

Not surprisingly, Millennial and first-time homebuyers are most concerned about not saving enough for a down payment. First-time homebuyers are nearly three times as likely as upgrade homebuyers (27% vs. 10%) to list this as their number-one concern about buying a home. Women are also more likely than men to worry about not having enough for a down payment.

There is a high correlation (+.70) between concerns for a job loss and ability to pay the monthly mortgage. Homebuyers who are most worried about a potential job loss or job move tend to rank difficulty paying their monthly mortgage higher as a concern that keeps them up.

Interestingly, repeat homebuyers, more mature homebuyers and homebuyers with higher household income are more likely to be concerned about prices falling after they buy compared to less experienced and lower-income peers. This might seem counter intuitive at first; one possible explanation is that these repeat and higher income buyers have first-hand experience with the last housing correction and have become more cautious. This is also true among homebuyers who plan to put down a bigger down payment. Concern for falling home prices after buying increases as a homebuyer’s planned down payment percentage increases.

In hot housing regions like California and Washington states, homebuyers’ top worries are their inability to find a home within their budget, and low housing inventory. They are also more likely to be concerned about home prices falling after they buy than about their ability to pay for the monthly mortgage payment.

Based on the research results, affordability continues to be a top concern among most homebuyers. One interesting takeaway is that repeat and upgrades homebuyers are more likely to be concerned about seeing prices fall after they buy. For months now housing industry watchers have been searching for answers to explain homeowners’ reluctance to sell – despite it being a sellers’ market – that had severely limited housing inventory and drove up home prices. In the same Value Insured survey, 83% of homeowners say now is a good time to sell, but 69% say they are concerned about prices correcting after they buy their next home. It is likely that we have found our explanation for more mature and experienced homeowners’ reluctance to sell, which has created a bottleneck. They need a plan for their next move before they sell, and so far, many do not see an affordable or low-risk path ahead.

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