How to Uncover a Client’s Real Pain Points in Sales

One of the biggest challenges in sales is when a conversation appears to be going perfectly. The prospect is engaged, agreeing with your points, and even complimenting your solution, but in the end, they decide not to move forward. It’s puzzling, especially when you’ve addressed every concern and handled every objection thoroughly.

More often than not, it’s because the “pain points” they gave you weren’t the real pain points. In fact, we’d venture to say many times the first pain points the clients give aren’t the real pain points at all!

Let’s say you spend an entire call trying to overcome a prospect’s objection about price. The buyer keeps saying, “We just don’t have the budget right now,” so you go through discounts, flexible payment options, even a stripped-down version of the package. Nothing works. Weeks later, you find out the real issue wasn’t money at all – the prospect was nervous their team wouldn’t adopt a new system. Price was just the easy excuse.

Does any of this sound familiar? If you’ve been in sales for even a short time, you’ve probably been there. The good news is that uncovering a client’s real pain points is easier than you might think. With a little practice, you’ll learn how to identify what really matters to them and close more sales in the process.

Let’s dive in!

What Do “Pain Points” Look Like?

First let’s discuss what “pain points” look like. Pain points are simply the specific problems, challenges or frustrations that drive a prospect to seek change. They are the triggers behind buying decisions and can often flow into objections. On the surface, pain points may look like simple objections (“The price is too high” or “We just need something faster”), but those are often symptoms, not the root cause.

We’ve found clients typically experience pain in a few broad categories:

• Product: The tool or service they have now isn’t meeting their needs but they’re not sure how your product provides a better solution.
  
• Price: The price is too high (or a concern).
  
• Process: They are not sure how to get from what they have now, to a better solution. Many times this comes in the form of internal resistance, lack of training, or overly complex processes.
  
• Performance: They are skeptical of a new vendor, or the performance they can expect from you or your team.

The problem is…prospects rarely state these deeper pains outright. Instead, they hide behind surface complaints. But successful salespeople know how to look beyond the obvious pain points they are offering and uncover the real objection.

Surface-Level Pain Points vs. Real Pain Points

You might also call this “external” vs. “internal” pain points. This is important because when prospects first start talking, they often share surface-level pain points. These are the quick, easy-to-identify issues like price, timing or features. For example:

• “We just need something cheaper.”
• “We need a faster system.”
• “Our tool doesn’t have all the features we need.”

While these sound reasonable, they often don’t tell the whole story. The real pain points lie beneath the surface and are usually tied to deeper business challenges.

For example:

Surface-level pain: “We need faster software.”

Real pain: “Our team is losing 20 hours a week due to system delays, and those delays are costing us $50,000 a month in lost productivity.”

Knowing the real pain leads to a very different conversation. The first version sounds like a feature request; the second explains a costly business risk.

Another common situation is when prospects cite external factors like price as the obstacle. For instance, a client might say, “Your solution costs too much,” when the real concern is:

• Switching feels risky – “What if my team rejects the new system?”
• They worry about the time and effort required for training.
• They fear a failed rollout will reflect poorly on them careerwise.
• They are hesitant to break a relationship with a long-standing vendor.
• They don’t have the confidence or authority to make the decision on their own (i.e., there is another stakeholder who needs to be involved.).

Sidenote: The latter is a different conversation entirely – you always want to ask up front and make sure you have all the decision makers present for your sales presentation, or at least that level of your sales presentation, if there are multiple steps: “Are you able to make the decision on your own, or is there anyone else who would need to be consulted? I totally understand. Let’s get John in on the call as well, so he can hear things firsthand and won’t be left out.”

Aside from this, the most common mistake salespeople make when they get an objection or pain point from a client is jumping straight into their pitch. Instead, focus on listening. People will reveal a lot if you simply let them talk without interruption!

Why Prospects Don’t Reveal Their Real Pain Points Immediately

Prospects rarely start by telling you what really keeps them up at night. There are a few reasons:

• Lack of trust: They don’t yet feel safe sharing vulnerabilities.
• Fear of exposure: Revealing challenges may feel like admitting weakness.
• Unawareness: Sometimes, even they haven’t connected the dots themselves to the true underlying issue. (You’d be surprised by how often this is the case.)
  

This is where empathy, patience and strong questioning skills set good salespeople apart from the rest. To get from surface-level to real pain points, you need to ask good follow-up questions:

• “Can you tell me more about how that affects your team?”
• “What does that look like on the client side?”
• “How is that affecting your sales?”
• “What happens if you don’t fix this problem?”
• “What would an ideal solution look like for you?”
  

You get the idea.

Dig Deeper with the “Five Whys”

If they are hesitant to share more, or you’re having a hard time getting information from them up front, this classic problem-solving approach works beautifully in sales. Start with an initial problem, then ask “Why?” up to five times until you uncover the root cause.

Example:

Prospect: “We need cheaper software.”

Salesperson: “Why is cost such a concern right now?”

Prospect: “Because our budgets are tight.”

Salesperson: “Why are budgets so tight?”

Prospect: “We’ve had delays in customer deliveries.”

Salesperson: “Why are deliveries being delayed?”

Prospect: “Because our current system can’t keep up with demand.”

Salesperson: “Why not?”

Prospect: “Because it takes too long to process orders, and we’re losing clients.”

Now you’ve uncovered the real pain point: lost clients due to inefficiency, not just budget concerns. Behind every business pain point lies a human being with personal stakes. A manager may worry about missing a promotion. A director might be under pressure from the board. An employee might feel burned out by inefficiencies.

Great salespeople tune in to these emotional drivers and acknowledge them:

Example: “I can imagine the stress of always playing catch-up must be exhausting. How has that impacted you personally?”

When prospects feel understood at both a business and emotional level, they’re far more open to solutions.

Isolating the Objection

When you think you’ve got enough information, you want to proceed to isolating the objection. For example:

• “Other than price, is there anything else that would keep you from moving forward?”
  
• “Other than concerns about the training, is there anything else that would keep this from being a great fit for your team?
  
• “Other than wanting to make sure the product is conducive with international clients, is there anything else that would keep you from proceeding with the transition?

Addressing the Pain

Once you’ve uncovered the real pain points, the next step is showing how your solution directly addresses them.

• Repeat the Pain Back to Them. One of the most powerful techniques is to restate the pain in your own words.

Example: “So what I’m hearing is that delays are costing your team $50,000 a month, and if it continues, you risk losing major clients. Is that correct?”

This not only confirms you’ve understood, but it reminds the prospect of the urgency.

• Position Your Product as the Specific Remedy. Tie every feature back to their pain point.

Example: “Our system automates order processing, which would remove the bottlenecks causing your delivery delays.”

• Reinforce Urgency by Quantifying the Impact. Help the prospect understand the cost of inaction.

Example:“If nothing changes, you’re looking at $600,000 in lost productivity over the next year. Does it make sense to continue at that rate?”

Using the CPR Method

A simple but effective framework is CPR:

1. Cut open the wound: Highlight the pain clearly.
2. Pour salt on the wound: Amplify the consequences of not solving it.
3. Provide the remedy: Present your solution as the fix.

Example:

“Your current delays are costing $50,000 a month. If this continues, it could mean losing key clients and damaging your reputation (cut + salt). Our platform eliminates those bottlenecks, ensuring orders are delivered on time, restoring client trust, and saving you significant costs (remedy).”

Close More Sales

Surface-level complaints like price or features are rarely the true drivers of decision-making. By listening deeply, asking probing questions and digging into emotional as well as business challenges, you can uncover what truly matters to your prospect.

Once revealed, their pain points become powerful motivators to the prospect. When you reflect them back, quantify their impact and position your solution as the clear remedy, you transform your role from salesperson to solution and/or a trusted advisor.

Related: Learn how to close more sales from professional sales and leadership coaches with our free guide Becoming a Closing Machine.

In the end, sales isn’t about selling. It’s listening and solving.  And the better you are at uncovering the real problems, the more successful you’ll be at providing the solutions that truly change your clients’ business.

At Southwestern Consulting, we help people like you close more sales and reach their goals. If you’re interested in training for your team, or how sales coaching might help you as an individual, we’re here to help. Reach out today for a free 30-min Strategy Session.