Empathy in sales: How to deepen insights about a client and their customers —

Posted: May 04, 2021

It can be especially hard to be empathetic as a salesperson. Empathy necessitates opening yourself up to people. You need to be vulnerable.

That’s often more difficult because sales requires a tough skin. No matter how good you are, you’re getting the door slammed in your face regularly. Yet you’ve got to be hoofing it all the time—activity is king, it drives sales, so you better not stop. To the extent we’ve toughened this steely, rejection-proof veneer, we leave less space for empathy.

Empathy helps us see the world from a customer’s perspective, to walk in their shoes. Empathetic sales people behave as if they work for the client.

That’s why we love Dan Pink’s clever reframing of ABC from “Always Be Closing” to “Attunement, Buoyancy, and Clarity.” In his book To Sell Is Human he, too, advocates close connection: attunement with clients, staying buoyant so that rejection doesn’t stop you, and a focus on clear insights that can create value. 

Empathy earns you the right to tell people the truth, even when it might be hard to hear.

There are deliberate steps to deepen empathy with a client and their customers. We’re going to discuss two of these: Customer Journey Maps and Jobs to Be Done.


Customer Journey Maps, as the name implies, portrays the experiences of customers with your client across a variety of touchpoints over time. But its real value—either to you or to a client with whom you might share your Journey Map—is not just the existence or sequence of touchpoints; it’s all about the customer’s experiences of those touchpoints. Journey Maps help us visualize the larger customer experience by revealing each step of the way—from walking in the door of our local Starbucks to taking the first sip of our latte—along with patterns of interaction and experience. They reveal high points and points of friction—both of which might be capitalized on by your client.

Your Journey Map can range from the highly unsophisticated, such as our example here, to the highly detailed, and there are plenty of templates to be had, courtesy of Google.

Generally, you plot the customer touchpoints from left to right along an x axis. Then, for each of those touchpoints, digital or physical, you plot customer experience on the y axis, a range of positive experiences increasing in posi- tive intensity above the x axis, and increasingly negative experiences below.

This tool’s value is that it can help you (and possibly your client if you share it) quickly determine moments of delight and moments of cringe. It could even help reveal patterns that are invisible when examined piecemeal. We’ve seen Journey Maps used very effectively to deepen discovery with clients for even more insight—where a moment of friction on the map sparks even deeper conversations about the underlying operations that cause it.


Tony Ulwich developed Jobs to Be Done,3 and it was popularized by Clayton Christensen from Harvard Business School.4 It started as a marketing tool and has since gravitated and morphed to the world of Design.

The tool follows the famous quotation from Theodore Levitt, an economist from Harvard Business School: “People don’t want a quarter-inch drill. They want a quarter-inch hole.” In other words, it’s easy to generalize about what people want and put it in terms of what we’re used to providing. In this example, a drill manufacturer sees customers as wanting their products. But that entirely misses what their customers actually want. Jobs to Be Done helps us get below the surface and connect with underlying motivations more effectively.

Here’s how you use the tool: whatever thing you’ve noticed—an experience, tool, product, service, and so forth—can be thought of as a job the customer is hiring it to do in order to accomplish something. If you’ve noticed a hack, it’s the converse—they’re firing something because it wasn’t doing the job they wanted. What job does the thing serve? What do customers want? What’s their motivation? What’s the outcome they’re seeking? Why is that important to them? Keep in mind that jobs aren’t solely task or function related. As our graphic suggests, we hire things to satisfy emotional needs as well—for ourselves and for others.


Empathy makes your insights more practical and powerful. What are people trying to do, and why is it important to them?

Salespeople typically focus on the attributes of the product being sold and the extent to which they match the client’s environment. It’s far more effective to focus on your customer’s motivation: whatever underlies and explains their thoughts and actions. 

You’re no longer a salesperson trying to impose and convince; you’re a team member helping frame and achieve a mutual goal. That’s also a competitive advantage for you as one of any number of potential vendors because other salespeople often don’t share this mindset.

When you’re empathetic, it’s easier to provide people critical feedback. Your insights could reveal some embarrassing gaps. If you’re not empathetic, people will likely get defensive. Empathy allows you to discuss issues in a way your client can engage and tackle them with you.


Connect with us to learn more about our Sell by Design training program for your team.

About the Author:


Ashley Welch is Co-Founder of Somersault Innovation. She has spent her career in sales and now partners with organizations to put the tools and practices of Design Thinking into the hands of sales professionals in order to drive human connection and grow revenue.