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Ask these 3 questions to elicit your customers’ pain points

Posted by Carol Mahamedi

November 1, 2021    |     4-minute read (694 words)

A pain point is a specific problem that prospective customers of your business are experiencing. They are usually complex, inconvenient and very troublesome. For business owners, a pain point is likely responsible for countless hours of wrangling, meetings and fruitless trial and error.

What are some common examples of customer pain points

  • Financial pain points:

    These entail situations in which customers sense their money is going to waste. An example could be an item that wears out quickly but that was advertised as long lasting.
  • Support pain points:

     Minimal clarity or communication at 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. 
  • Productivity pain points:

    Inefficient tasks that may be better off being outsourced. An example could be a store that does not have a rapid-ship option, or the amount of time it takes to grocery shop in person.
  • Process pain points:

    Problems stemming from business or personal processes.
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!

It is an unfortunate reality that most businesses grapple to comprehend their clients’ pain points. 

Businesses often struggle to understand their customers’ pain points because they can be complex, easy to misunderstand and defy a simple answer. Meanwhile, some customers aren’t even aware they have a pain point until it’s clearly identified for them. And in the same vein, some businesses are not aware that they are creating a pain point for their customers, such as an oddly laid-out store or a confusing website. 

To home in on your customers’ pain points, try posing a few of

these questions:

Note: These questions are best-suited to B2B conversations. However, they can be adjusted for B2C businesses too. 

  1. What do you consider the No. 1 issue holding you back from success?

This question often immediately elicits strong emotion. It’s likely that your customer has this roadblock in the forefront of their mind. They wrestle with it daily. To draw up out more information and home in on their pain point, ask a few questions such as: 

  • Which solutions have you tried already?
  • Who is most affected by this problem?
  • What would be different, specifically, if this issue was solved?
Don’t assume your customer’s first answer is their true pain point. Asking follow up questions like these will reveal their true pain point. Usually, the true cause of the pain will require more conversation to emerge. 

  1. Can you identify your boss’s primary concern?

Be aware that the pain point may be experienced by one level of a company very differently from that of a level above or below.

While you don’t want to undermine the customer you’re speaking with, keep in mind that their upline likely holds the wallet to make a final contract decision. As a best practice, try to have pain point conversations when every stakeholder is present. This ensures you attain the full picture and are able to create a solution the business can actually deploy. 

  1. What issues keep you from closing 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. 


Recognizing your clients’ pain points is an art, not a science. Identifying them requires practice, patience, a good understanding of your customer and a keenness to truly listen to them. But when you refine 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 effort.

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