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Ferret out your customers’ pain points by asking these questions

Posted by Grace Townsley

September 16, 2021

A pain point is a recurring issue that seriously disrupts your customer’s life. It’s often complex, hard to solve and is very bothersome. In a business, this pain point is probably the source of countless hours of debate, stress, meetings and failed attempted solutions. 

A few

common examples of pain points


  • Financial pain points:

    These involve situations where customers feel their money is wasted, like when they purchase products that wear out quickly but were promised to last a long time. 
  • Process pain points:

    Issues related to business or personal processes.
  • Productivity pain points:

    Wasted time due to inefficiencies or tasks that could be outsourced. Like a store lacking a fast-shipping option, or the time it takes to grocery shop in-person.
  • Support pain points:

    A lack of clarity or communication in critical times. Could be during the buying process, the install process, or even when a customer is wandering around a store unable to find the item they need. 
If a company can successfully solve their customer’s pain point, they’re practically guaranteed a sale. People strongly value solutions to the problems that keep them awake at night!

Unfortunately, many businesses struggle to understand their customers’ pain points, because they can be complex, misguiding, or disguised as another issue. Some customers don’t even realize they have a pain point until it’s clearly identified in front of them. Similarly, some businesses don’t realize they are creating a pain point for their customers, like an oddly organized store or a complicated website. 

If you’re struggling to understand your customers’ pain points, try asking a few of

these questions


Note: these questions work best in B2B conversations, but they can be easily adapted for B2C businesses too. 

  1. What is the biggest thing holding you back from success?

This question often immediately triggers an emotion. It’s likely that your customer has this roadblock at the top of their mind. They fight it every single day. 

You can follow up to get a bit more information and clarify their pain point with a few questions like:
  • What solutions have you tried already?
  • Who is most impacted by this problem?
  • What would be different, specifically, if this issue was solved?
Don’t stop at the first question and assume your customer’s first answer is their true pain point. Asking follow up questions like these reveal their true pain point. Often, the root cause of the pain takes a bit more conversation to uncover. 

  1. What is your boss’ major concern?

You might be surprised by how often the pain point experienced by one level of the organization is different from the pain point of a level up, or down. 

While you don’t want to undermine the customer you’re speaking with, remember that often their upline holds the wallet and will make the final contract decision. As a best practice, try to have pain point conversations with all stakeholders present. This ensures you get the full picture and are able to create a solution the company can actually deploy. 

  1. What issues usually stop you from closing business deals?

This question has the potential to reveal several pain points because so many factors go into making a successful deal. It can reveal issues with productivity, employee competence, sales processes and documents, accounting, and even the company’s reputation. 

It is a powerful question for two reasons – it helps you develop a solution that even the most bottom-line-focused companies will value. And, if you’re having difficulty recognizing your customer’s pain point with the other questions, this one can help get right to the point. 

Key takeaway

Identifying your customers’ pain points is an art. It takes practice, patience, a deep understanding of your customer, and a willingness to truly listen to them. But when you perfect the art, you’re able to tap into a group of customers who absolutely need what you have to offer. The benefits of being a pain point hunting expert are well worth the practice.  


Grace Townsley
Grace Townsley

As a professional copywriter in the finance and B2B space, Grace Townsley offers small business leaders big insights—one precisely chosen word at a time. Let's connect!

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