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Customer Pain Points: The Best Way to Uncover and Solve Problems

Customer Pain Points: The Best Way to Uncover and Solve Problems
Jenny Keohane
Jenny Keohane

Jenny Keohane

11 min read0 reads
Prospects, Sales, Sales Prospecting 


  1. What Are Customer Pain Points?
  2. The Types of Customer Pain Points
  3. Questions to Uncover Customer Pain Points
  4. Use Customer Testimonials to Share Solutions
  5. Align Sales and Marketing Data
  6. How to Show Customers That You Understand Their Pain Points
  7. Conclusion

What are the biggest challenges your prospective customers face? This question is something both your sales and marketing team must be experts on to drive business growth and revenue.

In both sales and marketing, you need to uncover your customers’ pain points in order to position your product or service as the solution.

But no customer is the same – sales reps must ask the right questions to present a solution that caters to that specific prospect and their business.

Let’s explore the best ways to uncover customer pain points, align insights, and solve these problems.

Here’s what we’ll cover:

user-groupUncover pain pointsAlways know what's resonating with prospects

What Are Customer Pain Points?

Pain points are issues or problems that are causing prospective customers of your business “pain,” requiring a solution.

Uncovering customer pain points ultimately affects both your sales and marketing strategy.

Salespeople want to figure out the prospect’s pain points so they can tailor their pitch and present the product or service they’re selling as the appropriate solution. And marketers want to understand these pain points so they can advertise/present their solution effectively and in an appealing and enticing way.

That’s why identifying and uncovering these pain points is so crucial.

However, uncovering customer pain points isn’t as easy as it seems and there is no one-size-fits-all tactic. In fact, some customers don’t even know the root of issues they’re struggling with.

The Types of Customer Pain Points

Customer pain points are often grouped into 4 main types: productivity, financial, process, and support.Types of customer pain points

Productivity Pain Points

Customers want to be more efficient with their time and are most likely wasting too much time with their current solution.

An example of a productivity pain point might be a manual process that takes hours to complete.

Financial Pain Points

Customers want to reduce their spend and are most likely spending too much money on their current solution.

A sample financial pain point could be a legacy software that costs more money than it saves.

Process Pain Points

Customers want to improve internal processes and are experiencing issues with their current systems and processes in place.

A process pain point could be internal project management among teams.

Support Pain Points

Customers are not receiving the appropriate support they need, especially at critical stages of the customer journey or sales process.

An example of a support pain point might be customers not knowing where to turn when they have a question.

Identifying the type of pain point your prospect is struggling with will help you position your solution and tailor your offer to their needs.

For example, if your prospect is struggling with financial problems, emphasize the ROI your customers are achieving or highlight average savings. Better yet, if your solution costs less than your competitors, make this loud and clear.

Questions to Uncover Customer Pain Points

When 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.

Discovering customer pain points: Ask 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.

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.”

Customer Solution 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.

Use Customer Testimonials to Share Solutions

Just because you’re saying you can solve your prospect’s 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.

For example, here at Yesware, we did a customer testimonial series earlier this year where we simply went on a zoom call and asked various customers questions about how Yesware solves their pain points.

Rather than filming it ourselves and making the testimonial look and sound glorious and professional, we allowed customers to sit in the comfort of their homes or offices and answer in whatever way they want. This helps make the testimonial as raw and genuine as possible.

Use customer testimonials to share solutions

These can be used for both marketing activities and your sales team can hand them off to prospects based on their conversations and pain points that arise.

Another way you can specifically address pain points is by providing case studies of how customers have achieved X, Y, and Z using your solution.

Here’s an example of how Yesware incorporates this:

see the ROI customers are achieving today

Make sure your prospects have access to real case studies and testimonials, giving them validation that your solution does in fact solve the issues they’re facing.

document-reportTrack all attachmentsView attachment opens & page-by-page breakdowns

Align Sales and Marketing Data

It’s all-important that sales and marketing are aligned and on the same page.

For example: sales team – what are the most common pain points that arise in discovery calls with prospects? Marketing team – what are the common struggles identified in your research and surveys? Figuring this out and aligning your data is key.

Your marketing team can conduct qualitative research – getting detailed responses from prospects.

For example, the Marketing team here at Yesware sent out a survey asking salespeople what their biggest sales challenges are right now.

uncovering customer pain points with survey question: biggest sales challenge

Asking the participants to leave a detailed response helped get us very thorough answers which gave us a deeper understanding of what our prospects are struggling with.

This not only helps us write content based on these pain points but informs both our marketing and sales team what business problems our target audience is currently facing.

Also, there’s plenty of research and studies online. You’re selling to salespeople? Search for the biggest challenges salespeople face.

What is the biggest challenge in sales?Source

There are various ways for both teams to learn more about your prospects:

  • Research
  • Surveys
  • Personal phone calls
  • Social Media
  • Online reviews
  • Competitors
  • Industry events

But the most effective way is to talk to them.

Once you and your marketing team are aligned – you both have the information you need about your prospects and customers to execute your strategies effectively.

In your marketing activities such as ads and landing pages – use emotional triggers that address very specific pain points. Grab the audience’s attention by addressing these pain points head-on and reinforcing why your product or service can ease your prospects’ pain.

In fact, 62% of customers want marketing content that speaks to pain points.

62% of customers want marketing content that speaks to pain points.

How to Show Customers That You Understand Their Pain Points

You’ve identified your customer’s pain, now you need to communicate how you’re going to solve it.

Your marketing team needs to create engaging and effective marketing pieces that leverage these pain points and draw emotional responses. And your sales team needs to present themselves as a solution provider rather than a straight seller.

The key here is to show your customers that you understand their pain points.

According to IBM, 78% of customers don’t feel understood by brands.

Customer pain points: understand your prospectsThat’s why it’s important to make your prospects feel understood. By making it clear that they’ve been heard – they’re more likely to listen to the message you’re trying to convey.

There’s no better way to solving your customer pain points than showing that you understand them and their problems.

Here are some effective ways of doing so:

1. Tailor Your Solution to Their Business

Present your solution in a way that solves their specific problems. Address their name, the company’s name, and any specific concepts or phrases they used to describe their pain points. Rephrase and incorporate these into your solution.

This not only shows them you were listening but makes the whole pitch much more personable (an essential element of a sales pitch).

2. Use the Same Language

Use your prospect’s language and terminology. This is a common method for building rapport and making the conversation feel more genuine and human.

Making it clear that you understand them is something that will put you ahead of many other brands.

3. Emphasize Solving This Pain Will Help Your Prospects Do

By leveraging these pain points and emphasizing ways their lives will be easier once they’re resolved, you open up a door and new perspective that will only motivate them to act fast on a solution.

4. Show How Your Solution Can Relieve This Pain

Make it clear how your solution will relieve these current struggles. Use social proof here, emphasize how customers of yours have saved X amount of time by leveraging your solution.

mailPersonalize all outreachPersonalize emails at scale with Yesware


All-in-all, your ability to discover and solve customer pain points will put you ahead of the game.

Remember, although customer pain points can be very similar, there’s no one-size-fits-all tactic for addressing and offering the best solution.

The key is to listen and personalize your solution to each customer.

And always remember the importance of sales and marketing alignment – share research, data, insights and you’ll only see progress in your ability to pinpoint customer pain points and help your customers address them head-on.

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