Let me level with you: I learned more about sales from Saturday afternoons with my grandma than I ever did in any sales training seminar. (True story—she made the world’s best cookies, insisted on hearing every detail of my week, and had a knack for saying the exact right thing at the exact right time.) This isn’t some nostalgia trip—but a hard-won discovery. Sales is, at its core, about real conversations, the kind you’d never find scripted in a business book. Let’s dive into how you can steal a page from grandma’s playbook and make your sales pitch more human—and a lot more effective. You can use empathy in sales with backchanneling in your conversations.
Section 1: Why Grandma’s Empathy Wins—Every Time
There’s a lot you can learn from a grandma when it comes to sales presentations. If you think about the most empathetic person in your life, chances are it’s your grandma—or someone just like her. Grandmas have a special way of making you feel heard, valued, and cared for. That’s not just heartwarming; it’s a masterclass in empathy in sales.
Grandma’s Style: Start with Warmth, Not the Pitch
When you walk into Grandma’s house, she doesn’t greet you with a list of chores or a sales pitch. Instead, she starts with warmth: a smile, a hug, and maybe a plate of cookies. In sales, this translates to putting the prospect at ease before diving into features or benefits. The first step to build rapport with a prospect is to make them feel comfortable and understood, not pressured. This is where most sales scripts and processes fall short—they skip the human connection and go straight for the close.
Empathy Cushions: Disarm with Care
Think about a tough moment—maybe you just broke up with someone. If you told your grandma, she wouldn’t rush to fix it or offer advice right away. She’d say something like, “I see. I’m sorry. That’s hard to hear.” These are cushioning statements in sales: simple, empathetic responses that acknowledge emotion and validate feelings. In sales conversations, using cushioning statements like “I hear you” or “That’s tough” disarms objections and opens the door to honest dialogue. Just like a plate of cookies, these statements make people feel safe and cared for.
Grandma will make it all better. I got cookies. I got cake. I got ice cream.
Real Sales Happen in the Comfort Zone
Real sales don’t happen in the closing zone—they happen in the comfort zone. When a buyer feels comfortable, they’re more likely to share their true needs, concerns, and motivations. This is where tactical empathy in sales comes into play. Tactical empathy means actively listening, validating the prospect’s feelings, and offering solutions that align with their values. It’s not about manipulation; it’s about genuine understanding.
- Back channeling—those little “mm-hmms” and nods—shows you’re engaged, just like Grandma listening to your stories.
- Empathy-driven sales approaches put the buyer’s needs above your talking points.
- People buy from those they trust, not those who rush to close.
When you use empathy as your foundation, you’re not just selling a product—you’re building trust. Grandma’s approach is proof: she listens, she cushions, and she makes you feel like you matter. That’s why her empathy wins—every time.
Section 2: Killing the Sales Script—One Conversation at a Time
If you’ve ever sat through a sales call that felt robotic, you know how quickly a script can zap the natural rhythm out of a conversation. People don’t talk in bullet points. They don’t follow a neat, linear path from “hello” to “yes.” Instead, real sales conversations are unpredictable, a little messy, and—at their best—genuinely human. This is where empathy and active listening techniques come into play, transforming your approach from scripted to authentic.
Why Scripts Fall Flat in Sales Conversations
Most sales scripts are written in what you might call “business format.” They’re structured, clean, and logical. But, as copywriting coach David Garfinkle (known as “Garf”) points out, “Most sales books do not type conversation format. They type business format. And so it can be super confusing.” The result? You sound more like a corporate memo than a trusted advisor.
Observational Techniques: The Coffee Shop Trick
Early in my sales career, Garf gave me an exercise that changed everything. He said, “Go to your local coffee shop. Listen to how people talk. Type out what they’re saying—not the content, but the flow, the rhythm, the real-life dialogue.” This wasn’t about eavesdropping for gossip. It was about using observational techniques in sales to capture the authentic conversation in sales settings.
- Notice the pauses and fillers: People say “um,” “you know,” and “like.” These aren’t mistakes—they’re part of how we build rapport.
- Spot the curiosity: Real conversations are full of questions, clarifications, and little asides. Sales magic happens when you’re responsive and curious, not just reciting lines.
- Watch for empathy cues: Listen for moments when someone mirrors the other’s tone or repeats a phrase. This is tactical empathy in action—meeting people where they are.
Sales Conversation Examples: Real Talk Beats Rigid Scripts
When you listen to real people, you’ll notice that conversations rarely follow a script. For example, a customer might say, “I’m not sure this is the right time,” instead of giving a clear objection. A script might tell you to push forward, but an empathy-driven approach encourages you to pause, ask a follow-up question, and show you’re listening.
Most sales books do not type conversation format. They type business format. And so it can be super confusing.
Building Authentic Conversation in Sales
To move beyond scripts, try these active listening techniques:
- Reflect back: Repeat what you’ve heard in your own words to confirm understanding.
- Ask open-ended questions: Invite your prospect to share more about their needs and concerns.
- Embrace the messiness: Allow for pauses, tangents, and genuine curiosity. That’s where trust is built.
By observing real conversations and practicing tactical empathy, you’ll find that the best sales conversations aren’t memorized—they’re responsive, authentic, and rooted in genuine connection. The next time you’re tempted to stick to the script, remember: people buy from people, not from bullet points.
Section 3: Speak Human First—Back Channeling and Building Rapport
When it comes to tactical empathy in sales, the difference between a pushy pitch and a genuine connection often comes down to the smallest details. One of the most overlooked active listening techniques is back channeling—those short, caring responses that show you’re truly present. Think about how your grandma listens: she doesn’t just wait for her turn to talk. She nods, says “I see,” or “That makes sense,” and lets you know she’s with you every step of the way. This is the heart of sales empathy skills.
Active Listening Isn’t Robotic—It’s Human
Many salespeople fall into the trap of jumping straight into problem-solving mode. The moment a prospect voices a concern, they’re ready with a solution—often missing the chance to validate the prospect’s feelings. As the source material highlights, “You miss this small element of like three to five words: I hear you. I got you. I understand. That makes sense.” These micro-responses are more than filler; they’re signals that you’re listening, not just waiting to sell.
- “I see.”
- “That makes sense.”
- “I got you.”
- “I understand.”
These phrases may seem simple, but they are powerful tools to build rapport with prospects. They keep the conversation natural and help prospects feel heard, not handled.
Back Channeling: The Timing Matters
Back channeling isn’t just about what you say—it’s about when you say it. Well-timed, authentic micro-responses can turn awkward sales moments into trust-building opportunities. If you jump in too quickly, you risk sounding insincere or interrupting the prospect’s thought process. If you wait too long, the conversation can feel cold or disconnected.
Pay attention to the natural flow of the conversation. Use back channeling at key moments—when the prospect shares a concern, expresses hesitation, or even cracks a joke. These are natural entry points for showing tactical empathy in sales. As the source notes, “There’s timing to the way that people interact and react to a conversation.”
Let the Conversation Breathe
Just like real friends, great salespeople know when to pause and reflect. Don’t rush to fill every silence. Give your prospect space to process and respond. This not only demonstrates respect but also encourages more open, honest dialogue.
You miss this small element of like three to five words: I hear you. I got you. I understand. That makes sense.
By integrating these active listening techniques and focusing on genuine back channeling, you humanize the sales experience. You shift from just making a sale to truly helping your prospect solve their problem. That’s the essence of sales empathy skills—and it’s what grandmas have known all along.
Wild Card: The ‘Headphones-in-the-Coffee-Shop’ Empathy Drill
Imagine this: You slip on a pair of headphones, grab your favorite coffee, and settle into a corner of a bustling café. But here’s the twist—your headphones aren’t playing music. They’re your camouflage, a subtle signal that you’re “tuned out” and not listening. In reality, you’re there for science: to observe, to listen, and to learn the art of natural dialogue in sales interactions. This is the ‘Headphones-in-the-Coffee-Shop’ Empathy Drill, a powerful observational technique that can transform the way you approach empathy in sales conversations.
Why headphones? Simple. When people think you’re listening, they’ll filter their words or even clam up. But with headphones on, you become invisible—free to witness authentic exchanges without intruding. Your job is not to react, not to judge, but to watch the interactions unfold. As one wise observer put it,
“Your job is just to watch the interactions… look for places where things are funny… where there’s agreement.”
Here’s where the magic happens. As you eavesdrop (ethically, of course), you’ll notice the subtle cues that make conversations tick. Listen for the timing—the pauses, the overlaps, the moments when someone leans in or pulls back. Watch how people validate each other’s feelings, using “cushioning” language like, “I totally get what you mean,” or, “That must have been tough.” These are the empathy-based connections that separate transactional sales from transformative ones.
Pay close attention to non-verbal cues, too. A raised eyebrow, a slight smile, a gentle nod—these gestures often speak louder than words. They reveal agreement, understanding, and sometimes, gentle disagreement, all without a single syllable. In sales, these observational techniques are gold. They teach you how to read the room, sense hesitation, and spot genuine interest, all skills that help you build rapport and trust.
Take notes on what you hear and see. Jot down snippets of real conversations, especially moments where people connect over shared experiences or gently disagree without breaking rapport. Notice how humor is used to diffuse tension, or how a well-timed pause can invite someone to open up. These are the building blocks of empathy in sales conversations—skills that can’t be learned from a script, but only from real, unfiltered human interaction.
Is this exercise a little weird? Maybe. But it’s also incredibly effective. By immersing yourself in the natural ebb and flow of everyday dialogue, you’ll develop a sharper ear for what matters to your prospects. You’ll learn to spot the genuine interests that spark conversation catalysts and create lasting, empathy-based connections. And just like grandma always knew, sometimes the best way to understand people is simply to listen—really listen—to what’s being said, and what isn’t.
So next time you’re in a coffee shop, slip on those headphones and tune in to the world around you. You might just discover that the secret to great sales isn’t in what you say, but in how well you listen.
TL;DR: Bring a little grandma-style empathy to your sales conversations and watch trust, rapport, and results flourish. The old-school approach works for modern deals: Listen better, respond with heart, and treat every dialogue like a relationship—not a transaction.
