The ability to understand what someone's going through? That's not a soft skill. That's your edge.
Here's the difference:
Without empathy: You pitch a solution without understanding the problem. You talk at people instead of with them.
With empathy: You understand what they're dealing with. You ask questions that show you get it. You position your solution in a way that addresses their actual pain point.
Client Looking at Security Options
I could've just sent pricing and specs. But I asked: "What's driving the need for this right now? Is it a specific incident, or are you planning ahead?"
Turns out, they'd had a break-in. Suddenly, this wasn't about comparing features—it was about solving a real problem.
I adjusted my pitch to focus on security and peace of mind, not just the product. That's empathy in action.
When Your Kid Says They Don't Want to Go to School
You don't just say, "Too bad, you're going." You ask, "What's going on? Did something happen?"
That's empathy. You're tuning in to what's underneath the surface. Sales is the same.
When a Client Says "I Need to Think About It"
Instead of pushing harder, you say: "That makes sense. Is there something specific you're unsure about, or is it more about timing?"
You're not trying to overcome the objection. You're trying to understand it. That's the difference.
The Truth:
Empathy = understanding what someone is going through so you can meet them where they are. It's not manipulative. It's respectful. And it's what separates good salespeople from great ones.
Every time you've helped a friend through a tough situation, you used empathy. Every time you've figured out what your kid really needed (even when they couldn't say it), you used empathy.
Sales just gives you permission to use it on purpose.
Action Step:
This week, before you pitch anything (in sales or in life), ask yourself: "What does this person actually need right now?" Then speak to that. Not to what you want to sell.
I want to give you a tool you can use before every single sales conversation. It's called the Empathy Map, and it's something I wish someone had taught me in my first year of sales. It would have saved me so many missed connections and lost deals.
Here's how it works. Before you get on a call (or even after, as a way to debrief), draw out four quadrants and fill them in for your prospect:
What are they THINKING?
What's running through their mind? Are they thinking about budget? About how their boss will react? About whether they can trust you? About the last vendor who let them down?
Example: "I'm thinking this sounds great, but my CFO is going to ask me hard questions about ROI and I don't have answers yet."
What are they FEELING?
What emotions are at play? Stress? Excitement? Fear? Pressure? Hope? Remember, behind every business conversation is a human being with feelings.
Example: "I'm feeling pressure because my team is burnt out and if I don't find a solution soon, I might lose key people."
What are they SAYING?
What words are they actually using? What questions are they asking? What phrases keep coming up? Pay attention to exact language—it tells you what they care about most.
Example: "We need something that's easy to implement. We don't have time for a big learning curve."
What are they DOING?
What actions are they taking? Are they shopping around? Dragging their feet? Responding quickly to your emails? Involving other stakeholders? Their behavior tells you their priority level.
Example: "They responded to my email within an hour and asked to schedule a call this week. This is urgent for them."
Fill this out for every prospect you talk to. Keep a running document or notebook. Over time, you'll notice patterns. You'll start anticipating what people need before they tell you. And that's when empathy stops being a skill and starts being your superpower.
This distinction tripped me up for years, and I see it trip up new salespeople all the time. It's the difference between connecting with someone and accidentally making them feel small.
Sympathy
"Oh no, that sounds terrible. I'm so sorry you're dealing with that."
Sympathy puts you above someone. You're looking down at their situation and feeling bad for them. It creates distance. The other person feels pitied, not understood.
In sales, sympathy sounds like: "Wow, that's a really tough spot to be in." It acknowledges the problem but doesn't move anything forward. It can actually make the prospect feel worse.
Empathy
"I understand what that's like. That kind of pressure changes how you approach everything."
Empathy puts you beside someone. You're standing next to them, looking at the same problem together. It creates connection. The other person feels seen and understood.
In sales, empathy sounds like: "That makes sense. When you're dealing with that kind of uncertainty, you need a solution you can trust to actually work." It acknowledges AND leads somewhere.
Here's the key: sympathy stops at "I feel bad for you." Empathy goes further to "I understand you, and here's how we move forward together." Only one of those leads to trust. Only one of those leads to action. Only one of those closes deals.
Real Talk from Katherine:
I once had a prospect tell me they'd just laid off 20% of their staff. My gut reaction was sympathy—I almost said, "Oh my gosh, I'm so sorry." But instead, I paused and said, "That's a really difficult decision. I imagine the pressure on your remaining team just increased significantly. Is that part of what's driving this conversation?" They literally stopped and said, "Yes. That's exactly it." That one empathetic response opened up a 30-minute conversation where they told me everything I needed to know to win the deal. Sympathy would have ended the conversation. Empathy deepened it.
Okay, I need to talk about something nobody in sales training ever mentions: you can burn out from empathy. And as women, we are particularly vulnerable to this.
When you're genuinely empathetic—when you truly feel what your prospects are going through—it takes something out of you. If you're talking to people all day who are stressed, frustrated, scared, or overwhelmed, and you're absorbing all of that? You'll be emotionally exhausted by Friday. Or sooner.
Here's what I've learned: you can understand someone's pain without absorbing it. Think of it like this. A doctor can understand that a patient is in pain and treat it effectively without feeling the pain themselves. They're not cold—they're professional. They've learned to be fully present and deeply caring without taking the pain home with them.
Three boundaries that saved my career:
1. I process after calls, not during.
After a heavy conversation, I take 5 minutes to write down what I learned and how I'm feeling. Then I close that mental file and move to the next call with a fresh slate. I don't carry one prospect's stress into the next conversation.
2. I separate understanding from ownership.
I can understand that a prospect is under enormous pressure without making their pressure mine. Their problem is theirs to solve. My job is to offer a solution that helps—not to carry their burden. This isn't cold. It's sustainable.
3. I have a hard stop at the end of the day.
When work is done, work is done. I don't replay difficult conversations in my head at dinner. I don't check emails after 6 PM. This boundary isn't just about productivity—it's about longevity. If you want a long, successful sales career, you need to protect your emotional energy.
Real Talk from Katherine:
In my first year of B2B sales, I was so empathetic that I'd go home emotionally wrecked. I was absorbing every prospect's stress like a sponge. One night my partner looked at me and said, "You seem more stressed than the people you're trying to help." That was my wake-up call. Empathy without boundaries isn't a superpower—it's a recipe for burnout. Set your boundaries now, before you need them. Future you will thank you.
Why empathy is a competitive advantage—not a soft skill:
The sales industry used to reward aggression. Push harder. Close faster. Overcome every objection. That era is fading fast.
Today’s best-performing reps build relationships. They make clients feel understood before they make them feel sold. That’s what drives referrals, repeat business, and significant deals through email—because the relationship got built so well that the client wants to come back.
You’ve been training for this your whole life. Not as a salesperson. As a person who actually pays attention to other people. That’s rarer than you think—and worth more than you know.
What you just learned shows up differently depending on which sales path you're exploring. Click your path to see how this applies to you specifically.
Empathy in B2B is about understanding business pressure—and the humans underneath it. The person you're selling to is rarely just evaluating your product. They're navigating budget constraints, stakeholder politics, competing priorities, and the very real fear of making the wrong decision. A bad vendor choice in B2B can cost someone their credibility, their bonus, or even their job. When you understand that weight, you sell differently.
Different roles require different empathy. A COO cares about operational efficiency and reducing risk across the organization. They're thinking big picture—how does this decision affect the company in 12 months? A procurement manager cares about getting the best deal without getting blamed if something goes wrong. They're thinking about protecting themselves. When you show empathy to a COO, you say things like, "I understand you need this to align with your broader operational goals." When you show empathy to a procurement manager, you say, "I know you need to feel confident that this is going to work before you put your name on it."
The best B2B salespeople I know don't just empathize with the person on the call—they empathize with the people NOT on the call. The CFO who's going to scrutinize the invoice. The end users who are going to have to learn a new system. The board members who are going to ask tough questions. When you can say, "I know your finance team is going to want to see this data before they approve anything—let me put together something that makes their job easier," you've just shown empathy for someone you've never even met. That's powerful.
Remember: in B2B, the decision to buy is almost always a group decision, even when it doesn't look like one. Your empathy needs to extend across the entire decision-making chain, not just the person you happen to be talking to.
Before you move on, let's make sure the key concepts really clicked. Answer all questions correctly to unlock the next lesson.
1. What is the key difference between empathy and sympathy in sales?
2. What are the four quadrants of the Empathy Map?
3. A prospect tells you they just laid off 20% of their staff. What's the most empathetic response?
4. Why is setting empathy boundaries important for a long-term sales career?
5. According to Katherine, what separates good salespeople from great ones?
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