Empathy Isn’t Optional in Sales. It’s Your Edge.
By Shane Gibson
I’ve been training and speaking to sales teams for over 25 years across five continents. I’ve coached everyone from solopreneurs bootstrapping a startup to enterprise sales teams handling eight-figure deals.
In every room, in every country, one principle holds true: People buy from people they trust, and trust doesn’t happen in a vacuum. It’s built on empathy.
The problem is, too many people still think empathy is soft; a “nice-to-have” skill to tack on after all the real sales training is done.
I’m not an empathy expert. I’d like to learn more and get better at teaching it. My partner, little woo, has her Master’s in Restorative Practice and Justice. Her work focuses on developing empathetic, restorative work and community environments. One thing I have gleaned from this body of knowledge that applies to sales teams… empathy is not a strategy it’s a culture. We need to embody it organization wide.
SALES TRUTH: Empathy is one of the sharpest sales tools we have. It’s how we read between the lines. How we uncover real motivations. How we build loyalty that competitors can’t shake loose with a cheaper price.
THE BAD NEWS FOR SALES LEADERS: Your team will only be as empathetic as you are.
Empathy starts at the top. You can’t tell your salespeople to be empathetic while you’re leading with pressure, quotas, and interrogation. So how do you build an empathetic sales culture? How do you train empathy into your people, not just as a concept, but as a real skill they can use to close business?
Empathy also starts from within for all of us. If we don’t have empathy for ourselves and a positive self-concept, it’s hard to give something we don’t have to others. As leaders it means we have to take responsibility for our own personal growth and healing if we are going to be able to embody empathetic leadership, and help create empathetic sales cultures. Assuming you’re doing the work…. here’s the next steps in creating salespeople and sales teams which are empathetic.
1. Redefine Empathy in Sales
First, we have to agree on what empathy means in a sales context.
It’s not about agreeing with everyone or letting clients walk all over you. It’s not about being overly sentimental or losing sight of your targets.
Empathy in sales is the ability to step into the other person’s world and understand:
- What pressures they’re facing.
- What’s at stake for them professionally and personally.
- What hidden fears might be driving their hesitation.
- What outcomes would make them feel safe and successful.
And then respond in a way that shows you get it.
From a sales perspective, empathy is the ability to connect emotionally while thinking strategically.
When a client or a team member feels truly understood, walls come down. Conversations get honest. And deals move forward.
2. Lead the Way: Empathy Starts With You
Let’s get real. You can’t fake empathy.
You can’t tell your team to listen deeply while you’re barking at them about quotas. Your people watch how you handle conversations—especially when things go sideways.
Picture this.
One of your top reps has been solid for months. Suddenly their pipeline dries up. They’re late to meetings. They seem distant.
You’ve got two ways to handle it.
The old-school approach:
“Your numbers are down. What’s going on? You need to fix it or we’re talking performance plans.”
Or you can take the empathetic route:
“You’ve been one of our top performers. I’ve noticed some changes lately. Is there something happening that I can help with? Is there stress outside work, or tension here we should talk about?”
One approach makes people defensive and fearful.
The other builds loyalty.
Salespeople don’t leave companies. They leave leaders who don’t listen.
Empathy is leadership insurance.
3. Make Empathy a Core Value, Not a Slogan
Empathy isn’t something you tack onto your sales pitch. It has to be baked into your culture.
Here’s what that looks like:
- Leaders start meetings by checking in with people as humans, not just producers.
- Performance conversations focus on finding root causes, not blame.
- Wins are celebrated not just for deals closed, but for relationships built.
- Salespeople know it’s safe to share concerns without fear of punishment.
Empathy is how you keep great people. It’s how you create a team that brings humanity into every client conversation.
This empathetic sales culture doesn’t just manifest in client interactions. It also shows up cross-functionally. Sales teams with high levels of empathy:
- Collaborate better with customer success
- Are less likely to have toxic competitive traits (stealing leads, hazing, hoarding info etc.)
- Have a stronger succession bench of future sales leaders
4. Empathy Is Trainable
Empathy isn’t a talent reserved for a few special people. It’s a skill. You can teach it, practice it, and improve it.
In my workshops and programs, I treat empathy the same way I treat prospecting, negotiation, or closing.
Here’s how you make empathy real and practical for your team.
Exercise #1: The Observer Drill
This is one of the simplest but most eye-opening drills I run.
- One person plays the salesperson.
- One plays the buyer.
- A third person just observes.
The observer’s job isn’t to judge the sales pitch. It’s to notice:
- Emotional shifts in the conversation.
- Moments when the buyer seemed guarded or uncomfortable.
- Body language cues signaling curiosity, resistance, or trust.
After the role play, the observer leads a debrief:
- “Why did you answer that way?”
- “How did you feel when they said that?”
- “Was there something left unsaid?”
Most people are shocked at how much they miss because they’re too busy thinking about what they’re going to say next.
Empathy starts with paying attention.
Exercise #2: Tell the Client’s Story
Salespeople love talking about their product.
But real selling starts when you stop thinking about your solution and start thinking about your client’s world.
I run this exercise all the time.
Pick a real client. Have the salesperson tell the entire story from the client’s perspective:
- What’s their day like?
- What challenges are keeping them awake at night?
- What’s the worst thing that could happen to them if they choose the wrong solution?
- What does a win look like for them?
This forces salespeople to connect the dots between what they sell and what truly matters to the client.
Exercise #3: Practice Silence
Most salespeople hate silence.
They ask a question and then immediately rush to fill the space. But often, the real truth comes out in the quiet moments.
Train your team to ask a question… and wait. Count to ten if they have to.
It’s uncomfortable. But silence is where real insight lives.
5. Bring Empathy Into Objection Handling
Too many salespeople treat objections like something to defeat.
An objection is rarely just about price or timing. It’s usually tied to fear or uncertainty.
Instead of arguing, an empathetic salesperson says:
“I understand. Can you tell me more about what’s making you feel that way?”
That one question often turns a defensive client into someone willing to open up and share the real issue.
Empathy keeps the conversation alive instead of shutting it down.
6. Empathy in Digital Selling
Selling online adds new challenges to empathy.
You don’t get body language on email. You don’t hear tone in a LinkedIn message.
So you have to be intentional:
- Personalize every touchpoint. Stop blasting generic messages.
- Refer to previous conversations so people know you’re paying attention.
- Engage in comments, not just private messages, to build public rapport.
- When a prospect goes quiet, check in with care, not pressure.
Digital empathy is about showing there’s a real human on the other side of the screen.
7. Frequency and Empathy Go Together
Persistence is crucial in sales. But without empathy, persistence becomes pushiness.
Empathy helps you read when it’s time to push forward, and when to pause.
When following up:
- Reference details from past conversations.
- Check in with value, not just “Are you ready yet?”
- Let prospects set the pace if they need time.
Empathy keeps you from being just another annoying voice in someone’s inbox.
8. Empathy and Team Dynamics
Empathy doesn’t stop at clients. It’s how your team operates internally.
An empathetic team:
- Shares insights without fear of looking weak.
- Helps each other navigate tough deals.
- Stays connected even when pressure is high.
As a leader, you set the tone:
- Protect your team from toxic clients.
- Recognize different communication styles.
- Make space for people to speak honestly.
Empathy builds loyalty. And loyalty is what keeps teams strong through market ups and downs.
9. Build Empathy Into Daily Habits
Empathy isn’t a one-time training. It’s a habit.
Practical ways to keep it alive:
- Daily Check-Ins: Start your meetings with a quick human check-in. “How’s everyone doing today?”
- Call Reviews: Don’t just look at technique. Discuss emotional signals picked up during calls.
- Celebrate Empathy: Reward reps who show empathy in tough situations.
- Document Learning: Keep a team journal of client insights and emotional cues. Review it monthly.
When empathy is part of the daily rhythm, it becomes second nature.
10. Empathy Drives Real ROI
This isn’t theory. Empathy drives measurable results.
Empathy does the following for sales pros:
- Shortens sales cycles because clients trust you faster.
- Protects accounts because clients feel valued.
- Builds a loyal team that performs at a higher level.
- Sets you apart from competitors stuck pitching features instead of understanding people.
Closing big deals isn’t about luck. It’s about building trust, asking the right questions, and showing up consistently.
Empathy is how you ask the right questions. It’s how you show up.
The Challenge
So here’s my challenge to you:
- Lead with empathy.
- Teach it like any other sales skill.
- Make it part of how you coach, sell, and build relationships.
Because when you build an empathetic team, you’re not just closing deals. You’re building a business people want to work for, and buy from, for the long term.
Empathy isn’t soft. It’s your edge. Use it.
FAQ: How to Build Empathetic Sales Teams and Empathetic Sales Cultures
Empathy in sales is about stepping into the client’s world to understand their pressures, fears, and goals. It enables emotional connection and strategic thinking, helping build trust and move deals forward.
Empathy is a powerful tool in sales—it helps uncover real motivations, build loyalty, and gain trust. It’s a sharp sales edge, not a soft skill.
Sales leaders must lead with empathy, not just talk about it. That means checking in with team members as humans, avoiding pressure-heavy tactics, and creating safe spaces for honest dialogue.
Yes, empathy is a skill that can be taught and improved through specific exercises, such as role-playing, client storytelling, observing emotional cues, and practicing silence.
Empathy should be a core value, influencing how meetings are run, how wins are celebrated, and how challenges are addressed. It should be part of daily habits, conversations, and leadership practices.
Empathetic salespeople explore objections with curiosity instead of defensiveness. They ask open-ended questions to uncover the real concerns behind a client’s hesitation.
Digital empathy involves personalizing outreach, referencing previous conversations, being human in follow-ups, and engaging publicly on platforms like LinkedIn to build rapport.
An empathetic team collaborates better, shares insights freely, supports each other, and maintains trust—even under pressure. Leaders play a key role in fostering this environment.
Daily check-ins, reviewing emotional cues in call reviews, celebrating empathetic behavior, and maintaining a team journal of insights are all ways to keep empathy front and center.
Empathy shortens sales cycles, protects key accounts, increases team loyalty, and differentiates you from competitors—resulting in better performance and stronger client relationships.
