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Charlotte Ward •

1: Empathy with Jenny Dempsey

About this episode

Week 1 Topic: Empathy in Support

Empathy gets a lot of airtime in support, but too often it stops at the job description. We sit down with customer experience leader Jenny Dempsey to unpack what empathy really looks like on the front line—and why leadership modeling, team culture, and practical guardrails determine whether agents can truly use it. From the first hello to the closing summary, we map the specific behaviors that show customers they’ve been heard while still moving the conversation toward resolution.

Jenny walks us through building a shared definition of empathy that fits your channels, your product, and your customers. We compare high-stakes roles like dispatch with day-to-day SaaS troubleshooting to show how the same fundamentals—listen, validate, clarify, act—scale across contexts. You’ll hear concrete ways to hire for the right signals using scenario-based prompts and writing samples, then score them with consistent rubrics that prioritize curiosity, respectful tone, and clear next steps.

We also tackle empathy fatigue. High-empathy teammates can burn out when volume surges and autonomy vanishes, so we outline safeguards that keep care sustainable: time buffers for complex cases, channel rotations, debrief moments after tough interactions, and coaching that favors cognitive empathy over emotional overreach. Finally, we address the biggest blocker of all—policy. If you measure only speed, you’ll get speed; if you reward thoughtful acknowledgment and precise solutions, you’ll get loyal customers. Tune in for a practical, people-first framework that lets empathy thrive without sacrificing efficiency.

I grabbed Jenny just as she'd moved into a new home and was waiting on her soft furnishings, which is why this episode is a little echo-ey!

Empathyjenny-dempsey

Transcript

Charlotte Ward: 0:14

Welcome to episode one of the Customer Support Leaders Podcast. I’m Charlotte Ward. From our very first week, we’re talking about empathy and customer support. So listen on for five leaders talking about that very topic. I would like to welcome as my very first guest on my very first episode of my very first podcast, the lovely Jenny Dempsey. Jenny, would you like to introduce yourself?

Jenny Dempsey: 0:45

Hello, I’m Jenny Dempsey. I’m so happy to be here. I am a customer experience manager for Number Barn. I also am the founder of Jenny Dempsey Consulting, where I do well-being in the workplace workshops and speaking and freelancing fun. Thank you so much. And it is fun, right?

Charlotte Ward: 1:11

Okay, so Jenny, our very first topic on the Customer Support Leaders podcast is all about empathy in customer support. And I know that this is a topic that’s particularly close to your heart. So I would love to hear your thoughts on how important empathy is in support, how you can foster it in a team, and indeed if you think it’s a trait or a behavior that can be taught.

Jenny Dempsey: 1:35

Such a good question. And empathy, you know, in every interview for our customer support agents, it’s one of the things that we all look for. I’m pretty sure it’s on every single interviewer’s checklist. Like, oh, does this person show empathy? Will they show empathy to our customers, to the team? Um, so we’re always looking for it. And then, you know, when we hire someone and they don’t necessarily display the type of empathy that we want because it may not come naturally, we sometimes wonder if, like, oh, well, maybe we have the wrong person. I think that empathy is something that it’s definitely necessary in customer service roles for internal customers, our teammates, and the external customers of actual people out there with our product or service. And I think that we all show empathy differently. You know, the ability to understand and share the feelings of another person can look one way for one person and another way for another person based on our own life experiences. And then we also, as a team, will mirror what our leaders do. So if we’re seeing our leaders in customer service doing something that’s very um maybe uh distant or that they’re not understanding or sharing the feelings, that can come into play for everyone on the team whether or not empathy is a natural skill. Because if the leadership is not displaying these, like the other people may not feel that they want to or can, it may not feel as important. But then I’m gonna toss it around too. There’s empathy fatigue where there are some people that feel so much and will do so much that they burn out simply because their ability to understand and really like share the feelings, like it’s just so much. Um, they feel all the feels of everyone else.

Charlotte Ward: 3:29

You know what, Jenny, I think that’s really interesting what you said there about people can be very empathetic, but if they’re hired into an organization where leadership aren’t necessarily willing or able to display that level of empathy to customers for whatever reason, whether that’s some some perceived lack of value in the service or whether it is just a personal kind of approach to the workplace, whatever that is, that must be a a place of turmoil for those people on the front line who are very empathetic if they don’t feel they have that empathic support from leadership.

Jenny Dempsey: 4:07

Absolutely, absolutely. And you know, they may feel that that gets a little blocked where they have all the this feeling, they they feel very strong, you know, towards wanting to help the customers, but maybe you know, it could even come down to they’re not given the right tools to help the customers, they’re not given the amount of time that they need to help the customers, they’re rushed through a call, so they can’t even show this true empathy because you know, whoever set the rules and policy doesn’t give the team the the opportunities to release the empathy, I guess, in a way.

Charlotte Ward: 4:42

Yeah, yeah. Set it free. Set it free.

Jenny Dempsey: 4:45

Set it free.

Charlotte Ward: 4:47

So, how do you hire for empathy?

Jenny Dempsey: 4:50

So I think this looks different for every company, and it really also comes down to the culture. I think every company has to define what empathy really looks like for them. You know, we all have different ways of communicating with the customer. And in a nutshell, I mean, we could say it’s understanding the customer’s needs, asking the right questions, supporting them with um supportive words, kind words. There’s really no, at least in my opinion, and from working at so many different companies, empathy really looks different. Um, but there’s the same underlying basics, but it’s gonna look different for every company. And there’s an importance there for the company to define what empathy means to them. So when they’re in the interview, um they they do know what to look for and everyone’s on the same page.

Charlotte Ward: 5:39

In what ways do you think it’s significantly different then across companies? I I guess just in just in how it’s exhibited, really, more than anything specifically personal to the to the potential employee.

Jenny Dempsey: 5:53

Right. So, and I think it comes down to what the custom what the customer service agent would be doing. Um, for example, someone in a dispatch role who’s answering 911 calls is gonna need a different different level of empathy than someone who’s answering tech support calls for uh computers. But there is still the same underlying basics where someone needs the customer needs to be heard, the customer needs to be respected, the customer, you know, the agent needs to understand that whether it’s a computer or whether it’s someone’s hurt, the basics are there, but it’s like what is the agent actually going to be doing? And that needs to be clearly defined and shared with the team.

Charlotte Ward: 6:32

And and modeled well by by leadership is really important too, as you said. Yes. That’s all for this session. Go to

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