Week 1 Topic: Empathy in Support Ever felt the heat of a rushed customer and wondered what’s really driving it? We dive into how empathy becomes a practical edge in customer support, not just a feel-good value. With Matt Dale , VP of Customer Support at Illuminate Education, we unpack what it takes to train a team that serves K–12 educators under tight deadlines and constant pressure, and we draw a clear line between helpful empathy and the kind that derails priorities. We start by reframing empathy as a trainable, performance-driving skill. Matt shares how onboarding goes far beyond product knowledge to immerse new agents in the reality of teachers’ days: short prep windows, layered reporting structures, and the pressure of getting grades right before students rush back in. That context changes the tone of every call—agents stop taking urgency personally and start guiding decisively. We explore role plays, call reviews, and language cues that help agents mirror needs, match pace, and keep conversations moving toward resolution. Then we tackle the hard part: over-empathy. Feeling a customer’s frustration too deeply can skew judgment, push for the wrong fixes, and burn out your best people. Matt outlines how cognitive empathy—understanding context and acting with clarity—protects team health and keeps priorities aligned with impact. We compare a 1% bug to a 30% issue, discuss triage and workarounds, and show how expectation setting turns tense moments into trust-building outcomes. You’ll hear specific tactics for de-escalation, prioritization, and coaching agents who care deeply without carrying the weight home. If you lead support, manage product feedback, or serve educators, this conversation offers a toolkit: context-first training, cognitive empathy, impact-driven prioritization, and sustainable ways to care without burning out. Listen, take notes, and then share your take: where do you draw the line between caring and over-caring?
2: Empathy with Matt Dale
About this episode
Transcript
Charlotte Ward: 0:14
Welcome to episode two of the Customer Support Leaders Podcast. I'm Charlotte Ward. This week we're talking about empathy, so stay tuned for five leaders talking about that very topic. I'd like to welcome to the show today my good friend Matt Dale. Matt, would you like to introduce yourself?
Matt Dale: 0:39
Sure. I'm the VP of Customer Support at Illuminate Education. We're a K-12 software company based out of Irvine, California. We serve the K-12 school market here in the US. We've got several offices kind of all over the country, as well as a new team that we're setting up in India. And I've been with the company here about eight years. Started off as one of the first people on support. Our team is now just over 60 people. So we've we've had a lot of growth over the last few years and it's been an interesting journey.
Charlotte Ward: 1:08
Excellent. All good fun. Thank you.
Matt Dale: 1:11
Sure.
Charlotte Ward: 1:12
Okay. I'd love your opinion on how important you think empathy is in customer support. Do you actively foster it in the team? Do you think it's a skill that can be taught or is it more of a character trait that you just got or you don't got?
Matt Dale: 1:26
I agree that I think it's very important as people who are support professionals to be able to understand where our customers are coming from, to be able to relate to them in their struggle and understand kind of how they're seeing the world. And then help them go from that point to where they have successful resolution of whatever they're whatever they're struggling with. When we're able to get into their heads and walk a mile in their shoes, so to speak, it makes us more effective, I think, as support professionals. So I think it's a valuable skill. Just like any skill, I think we all as human beings come with a based on our genetics and our upbringing, we have different um levels of ability in that area. You know, um, some people are very empathetic and others are not not as much. And I think most folks can in any particular skill or or area, you can get better. Now that's not to say, you know, I I love motorsports, I love watching racing and things like that. And I like driving my car quickly, and I like uh doing autocross, which is you know, go out in a parking lot, a bunch of cones, and you try to put down the quickest, you know, 30 seconds or whatever it is in between cones. And it's not as scary as going out on the big track and you know, you're not going 120 miles an hour, you're not usually out of second gear, uh, but it's about car control and things like that. And I'm a good driver. I am not Formula One material, and I'm not at the level that a that a professional would be. And I have a friend, and he's he's a he's a better driver than I will ever be because he's just naturally better at it. You think about sports too. There's some people that are just very gifted at sports. There are people that are you know innately just aware of where their body is and they're able to be coordinated and stuff like that. And so just like those physical skills, um, I think I think empathy is is is like that too. So I've met some.
Charlotte Ward: 3:03
Something that you're just a little more, just something you're a little more in tune with as a as a human.
Matt Dale: 3:07
My wife, for example, uh Danielle, she's she is amazingly um empathetic. She understands why people are thinking what they're thinking and why they're doing what they're doing. She's like, oh, did you see that? That's because of this. And you come to find out that that she's exactly right. She's understood the motivation behind and she understands why they're feeling the way they're feeling. I'm a little less on that scale. Um to bring that all back to support then. Um I think it's helpful to work as part of the onboarding process and part of the training process to ensure that your people are developing those skills of empathy, whether they have them and then helping kind of hone them and get them to feel the right amount for the customer or whether they don't have them as much and helping them understand where their customers are coming from. So, for example, our customer base is all primarily teachers and educators. Most of us have gone through school at some point or another, uh, but we haven't been on the other side of the desk there. We haven't gone through what a teacher goes through. And so we spend a lot of time in the first couple weeks of training talking about what it's like to be a teacher, what they're experiencing in a day-to-day environment, what it's like with the, you know, how the different reporting structures happen in the district and where the pressures are coming from. Um, and that helps us, helps our people know more when they're talking to someone on the phone and they're having a, you know, they're they're quick and they're trying to get something done quickly. You know, it's because that person's got a prep period, and then this is the only time the day that they have students out of their classroom, but they've got to get the grades set up properly so that that they can finish the grading process tonight. Understanding that.
Charlotte Ward: 4:32
So your agents have got a huge amount of context.
Matt Dale: 4:35
So they're not going, oh, this guy's just mad at me because he it's not because he's having a bad day. He's he's just got it like he's got five minutes right now, and this is the only time today that he can have to get help. He's not angry at me, he's frustrated, he doesn't know what he's doing. How can I help de-escalate the frustration so that I can get him to you know where he needs to be for just so he can get that information, get his problem solved, and he can do the job that he needs to do before his kids come rushing back in after recess, and and he can continue on with his day. There's one other aspect of empathy on support that I've noticed that I think is different, and that is people that are actually too empathetic, that they're feeling too much of what the customer is feeling, and it actually impairs their ability to get the job done well. Like we have a software product, software is inherently broken, buggy, doesn't work the way it should. And you know, we've had agents in the past where they felt really deeply, oh my gosh, this is so bad for the customer, we need to get this fixed right away. Agreed, that it is a problem for this customer, and there's there's stuff going on, but it's affecting you know 1% of our population. That's not going to fit on the roadmap for development perspective over something that is affecting 30% of the population. And so in being overly empathetic because they're naturally attuned that way, they might actually be doing the customer a disservice and our team a disservice.
Charlotte Ward: 5:45
You're right. It there is that absolute personal involvement, which is not necessary in support. Listeners, if you go over to customersupportleaders.com, you will find an article I wrote on empathy quite some time ago, which talks about the type of empathy that you're talking about, Matt, which is cognitive empathy. It's basically the ability to take on board that context, to understand intellectually and objectively what the challenges are that the customer is experiencing, but to rationalize it in a very objective way and allow you to still go through the problem solving process. I think that's what you need. You don't want that level of personal involvement because it's not productive to the problem solving process, but also you're gonna burn out very quickly with that. That's it for today. Go to customersupportleaders.com forward slash two for the show notes, and I'll see you next time.