How to Identify & Empathize with Customer Pain Points to Solve Them Once & For All

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When it comes to B2B sales, decision-makers don’t really buy from brands or companies. In fact, according to IBM, 78% of customers don’t even feel understood by brands. (

At the end of the day, people buy from people — namely, people they’ve come to trust, who genuinely understand their business challenges and want to help them win. To establish this relationship, start with your prospect’s pain points and understand their impact on the customer’s business.

Here’s how sales professionals can discover and utilize this data to drive more successful sales conversations:

What are Pain Points?

Pain points are the specific problems, challenges, or frustrations experienced by your potential customers. These pain points can vary depending on the industry, target audience, and individual needs.

For example, a pain point for a mid-market business owner might be the difficulty of choosing, deploying, and using a customer relationship management (CRM) system. Understanding this pain point allows sales professionals to tailor their approach and offer a cost-conscious, easy-to-start solution that addresses these concerns. 

Identifying and addressing these pain points is essential for successful sales prospecting and customer relationship management.

Understanding the Four Types of Pain Points

There are four main categories that pain points boil up to: financial, productivity, process, and support.

Understanding the categories that your prospect’s individual pain points belong to can help you guide your sales conversation toward a targeted solution that addresses the root cause of their day-to-day issues. This not only builds trust and rapport, and establishes you as a trusted source of advice and information, but it also increases the likelihood they’ll adopt your solution.

What is a Financial Pain Point?

A financial pain point refers to a specific problem or challenge that a customer or prospect is facing that directly relates to revenue, income, or expenses. In B2B sales, these pain points will relate to budget constraints, costs, and the need for cost-effective solutions that provide a return on investment.

Examples of B2B Financial Pain Points:

  • High monthly expenses that exceed income
  • Concerns about the return on business investments
  • The cost of your solution or services
  • The cost of internal staff and personnel 

What is a Productivity Pain Point?

Productivity pain points are specific challenges or obstacles that hinder a business from achieving efficiency and efficacy. These pain points can vary from organization to organization, but they generally result in decreased output, wasted time, and missed opportunities. 

Examples of B2B Productivity Pain Points:

  • Inefficient sales prospecting methods, such as spending too much time on unqualified leads
  • Poor customer relationship management, leading to missed follow-up opportunities and lost sales
  • Lack of organization in tracking and managing sales leads and opportunities
  • Ineffective time management and prioritization of tasks
  • Overwhelm by multitasking and juggling too many responsibilities
  • Technology and tool limitations, such as outdated or cumbersome systems

What are Process-Related Pain Points?

Process-related pain points are the challenges or obstacles that a business encounters during the various stages of the sales and service process. These pain points can hinder the smooth flow of sales and customer support activities, and lead to inefficiencies and missed opportunities. 

Examples of B2B Process-related Pain Points:

  • Inefficient lead generation and prospecting strategies
  • Difficulty in qualifying leads and identifying potential customers
  • Ineffective customer relationship management and follow-up processes
  • Lack of clarity and consistency in the sales and service process
  • Inadequate outreach automation and technology tools
  • Lengthy and complex sales cycles
  • Poor alignment between sales and marketing efforts
  • Inaccurate or outdated sales data and information
  • Inefficient communication strategies between departments

Support-Related Pain Points

Support-related pain points are issues or challenges that a business knows its customers experience when seeking support from sales or customer service. These pain points can stem from various sources, including accountability and people-related challenges.

Examples of B2B Support-related Pain Points:

  • Lengthy wait times for a response or resolution
  • Inconsistent information provided by different team members
  • Rude or unprofessional interactions with customer service representatives
  • Inefficient communication between departments
  • Lack of accountability or visibility 
  • Unhelpful customer service teams and processes

The Role of Pain Points in Sales Prospecting

Sales & marketing teams see an average increase of 20% in sales when providing personalized experiences. ( By personalizing your approach and tailoring your message around a prospect’s specific pain, your solutions immediately feel more relevant and notice-worthy. For example:

Imagine you’ve got a splitting headache, but you’ve got a meeting in 30 minutes. You stop by a drug store and walk through a medicine aisle with dozens of solutions, and there’s an endcap with a new product that promises relief in 15 minutes or less. Statistically, the likelihood that you’ll choose that solution over the rest of the options in the aisle is much higher because it addresses your current pain point: time.

This kind of understanding not only helps in building stronger customer relationships but can also transform cold outreach into warm leads. When sales teams can demonstrate a genuine understanding of the customer’s pain points and offer a solution to alleviate them, it creates a sense of trust and a higher likelihood of the prospect being open to engaging with the sales process.

By focusing on the customer’s pain points, you can position your product or service as the best pain reliever on the market. 

Find Out Where it Hurts: Discovering Pain Points

Identifying the pain points in play for your target market will involve a combination of research and real conversations. Here are six surefire ways to discover the pains plaguing your prospects right now: 

Ask Genuine, Open-Ended Questions

Open-ended questions are the most important tool in sales discovery. These questions encourage your potential customers to share their thoughts, feelings, and experiences without restricting their answers to a simple ‘yes’ or ‘no.’ By asking open-ended questions, you can gain a deeper understanding of your prospect’s needs, challenges, and goals.

These types of questions allow you to uncover valuable insights about the issues your prospects are facing, which in turn enables you to offer tailored solutions to address their specific pain points. 

Uncover Your Prospect’s Pain Points with These Examples:

Steal these open-ended questions for your sales reps to uncover a prospect’s pain points:

  1. “Can you tell me about any challenges you’re currently facing in your business/role?”
  2. “What are the biggest obstacles or frustrations you encounter when trying to achieve your goals?”
  3. “How would a perfect product/service help make your job easier or solve any specific problems you’re dealing with?”
  4. “What aspects of your current solution or process are causing the most headaches or inefficiencies?”
  5. “What do you think is preventing you from hitting your goals right now?”

By asking these types of open-ended questions, sales reps can gain valuable insights into their prospect’s pain points and tailor their pitch to directly address those issues. 

Analyze Your Existing Customer Data

This is where having a great CRM can pay off. To analyze your existing customer data, start by looking at the patterns in customer data to identify the common pain points that led to a successful sale. This may include your customer’s journey on your website, forms submitted an resources downloaded, sales process feedback, or support interactions. Look for trends or recurring issues that your solution addresses effectively.

You can categorize the pain points you discover into specific groups, such as by product or persona, to better understand and target the needs of potential leads. Then, use this information to inform your sales strategies and messaging. 

Conduct Interviews & Create Case Studies

When it comes to identifying the pain points your product or solution best solves, conducting interviews and creating case studies can be invaluable tools. By asking the right questions and actively listening to the responses, you can uncover the pain points that your solution is uniquely positioned to address.

Case studies can also provide valuable insight into the pain points your solution can solve. By examining real-world examples of your solution in action, you can identify the specific challenges it addresses and the impact it has on the customer’s business. This not only helps you understand the pain points your solution is best suited for, but it also provides concrete evidence of its effectiveness, which can be a powerful selling tool.

Monitoring Online Reviews & Search Volume to Identify Pain Points

71% of B2B decision makers start their solution research with search engines.( Monitoring online reviews and search volume for your solution can help you gain insight into the specific issues or challenges that people are seeking solutions for.

Online reviews can provide valuable information about the experiences and frustrations of customers. Look for common themes or recurring complaints in the feedback. This can help you pinpoint the pain points and gaps that your product or service can address.

Analyzing search traffic can reveal what people are actively seeking solutions to. Using tools like Google Analytics, Google Search Console, and Semrush or Moz can help you track the keywords and search phrases that are leading users to your website and competitor websites. Are there certain problems or needs that are consistently driving traffic to your site? 

This information can then be used to tailor your sales approach and customer relationship management, ultimately improving your ability to connect with and address the needs of your target audience.

Scope Out the Competition

Research your competitors’ products and services. Look for information on how they position their solutions and the specific problems they aim to solve for their customers. Pay close attention to the language and messaging they use to address these pain points. How does your solution differentiate itself from your competition when it comes to this pain?

Consider reaching out to customers who have switched from your competitors to your company. Ask them about the pain points they experienced with the competitor’s solution and how your offering addressed those concerns.

Talk to Your Sales Team About Their Discovery Conversations

Regular sales and marketing alignment conversations are crucial for maintaining a feedback loop. When your sales team discovers new or important pain points, that information should be fed into marketing strategies and content creation, ultimately leading to more targeted and effective marketing campaigns.

This alignment enables the sales team to provide feedback on the effectiveness of marketing materials and campaigns, contributing to continuous improvement and refinement. By leveraging the pain points discovered in sales conversations, marketing teams can develop more impactful messaging and materials that directly address the pain points and challenges faced by potential customers.

Tailoring Your Solutions Around Your Prospect’s Pain

Now that you know what challenges your prospect is facing, you can customize your sales pitch to show how your product or service directly addresses those specific pain points. 

Start by doing your homework. Research your prospect’s industry, company, and any recent challenges they may have faced. Tailor your pitch to address those issues directly — giving a generic pitch that’s entirely focused on your product is a big mistake. Your pitch needs to demonstrate an understanding of their pain and help them see a better future for their company.

Focus on the value your product or service brings in alleviating those pain points. Highlight specific features or case studies that demonstrate how similar customers have used your product or service to overcome their challenges. Your pitch has to be personalized and relevant.

Actively listen to your prospect during the conversation – don’t flip through your slides giving a pre-prepared speech. Stop and ask those open-ended questions, and listen to the responses. Worry less about getting through your whole pitch than about making a genuine connection. You can always send your slide deck and schedule a follow-up conversation after the meeting ends. 

1. Give Your Prospect Options and Empower Them to Choose

By framing your solutions as direct responses to specific pain points, you can capture the interest of your potential clients. Build from that opportunity and give your prospect options for a path forward. 

For example, if a potential customer’s pain point is the high cost of software options, you can offer a solution that highlights the benefits of your system on operational efficiency. Help them see the purchase as an investment that will be offset by gains in other departments. Alternately, offer a free trial period and help your customer import their data and use the software the first time. This helps establish your partnership, and gives them a cost-free entry point. 

By directly addressing their concern about cost, you’re showing understanding and providing a solution that meets their needs. 

2. Speak Their Language

Mirroring your prospect’s language is a powerful tool in sales prospecting. Pay close attention to the words and phrases your prospect uses, and then using those same words and phrases in your communication with them. 

Take note of the specific words and phrases they use when describing their challenges or desired outcomes. Then, incorporate those same words and phrases into your responses, whether it’s in emails, calls, or in-person meetings.

For example, mirror the way they refer to their customers: do they say client, user, customer, or purchaser? 

3. Emphasize the Benefits of Solving the Pain Now

Most people won’t take action to purchase a new solution or service until their pain is severe. You can focus on the business benefits of solving their pain point now, rather than waiting for a crisis to occur.

Open-ended questions are a great way to start this part of your discovery conversation. One of the criteria you’re likely trying to establish in your early conversations is the prospect’s timeline for purchasing a solution. If their timeline is far-flung, consider asking questions like:

  • “What will change for your business between now and then?”
  • “Is there a reason you’re waiting until that time?”
  • “Are there any negative impacts your business could experience if you wait to address this problem?”

Depending on the answers, you may find that there’s an opportunity to showcase the benefits of acting sooner rather than later, like limited-time financial offers or risk mitigation. 

4. Show How Your Solution Will Relieve the Pain Once and For All 

Highlight the features, benefits, and differentiators of your product or service as they relate to the key pain point you’ve identified. Show the prospect how they can end their pain, and paint a picture of the outcome waiting for them on the other side of action. 

Your messaging matrix is the most valuable tool at this stage. It should clearly identify the problems and pains you solve, the differentiators your sales team can lean on, and the ultimate outcome your prospects can expect when they choose you. 

Testimonials and case studies are also powerful tools in showcasing real-life examples of how our solution has successfully relieved pain points for other clients. By sharing success stories and social proof, you’ll build trust and credibility with the prospect. This can help them visualize the potential impact your solution can have on their pain points.

Common Mistakes to Avoid When Leveraging Pain Points in Sales Conversations

  1. Making assumptions about a prospect’s pain points without data to back it up. This can lead to misdirected outreach and a missed opportunity to connect with the prospect. Instead, take the time to gather and analyze data to understand the prospect’s specific pain points before reaching out.
  2. Failing to follow up after identifying a prospect’s pain points. Once a pain point is identified, it’s important to follow up and offer a solution. Failing to do so can leave the prospect feeling unheard and unimportant.
  3. Focusing too heavily on your solution instead of the prospect’s journey. Your sales and marketing messaging should be customer-centric. Help them see themselves as the hero of the story. You’re just a guide, and your product or service is just a tool. Focus on what they can achieve, not on what you’re selling.
  4. Getting a little too creative with the way you communicate results. Testimonials and case studies are important tools, and you should ensure they stick to the facts. Avoid over-embellishment and dishonesty. If your results are unbelievable, make sure you offer proof. Can your case study subject also be a contactable reference, for example?

Watch out for these pitfalls. Do your research, ask more questions, follow up after each touchpoint, focus on the ideal outcome for your prospect, and be honest about the results your prospects can expect. 

Be a Pain Killer: Build Long-Term Relationships 

By offering personalized solutions that directly address your prospect’s worst pain points, you’re establishing a relationship as a trusted advisor and business partner. That relationship can’t be abandoned after the sale.

Following up with the customer after your deal is won should be a shared responsibility between your sales and service departments. Sales should reach out to gather feedback on the effectiveness of the solution sold. Make sure your customers are getting the full value of what they purchased:

  • Is the pain diminishing?
  • Have they adopted your solution to great success, or are there roadblocks you can help knock down?
  • What’s next for their business?

Make sure you facilitate a comprehensive handoff to your service department, and be sure your customer knows how to contact you if they need you. Open, continuous communication further solidifies your relationship, even after they sign on the dotted line. This investment of time pays off as it reduces churn, opens opportunities for upselling or cross-selling, and sets the foundation for mutually beneficial referrals in the future.

Before, during, and after a sale, stay focused on your prospect’s pain points. Whether you’re new to sales or a seasoned pro, remember: success is all about finding the right prospects, understanding their needs, and building strong relationships that drive results.

Get more sales strategies you can use. Take a look at our Ultimate B2B Sales Leader Guide.

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Ryan Mack

Ryan Mack is the CEO and co-founder of Peer Sales Agency. Fueled by his drive to help companies reach their revenue goals, he puts his decades of experience in sales, private equity, and organization leadership to work for Peer’s clients.


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