November 18, 2025: Ever wonder why empathy gets dismissed as a "soft skill" when it's actually your most powerful leadership tool? Eric Williamson went from being what he calls an expert jerk to becoming a jerk expert, and his transformation story will change how you think about workplace dynamics. From invisible disengagement in hybrid teams to managing star performers who steamroll everyone, Eric shares practical wisdom on navigating today's most challenging leadership scenarios. Discover his three-step AAA method for staying measured under pressure, learn why your one-on-ones might be completely missing the mark, and find out how to hold people accountable without losing your humanity. This conversation is packed with real talk about creating connections in environments where face-to-face interaction is increasingly rare.

Key Points:

• 01:25 Eric's Transformation Journey
• 02:28 The Importance of Empathy in the Workplace
• 04:21 Recognizing Jerk Behavior
• 07:35 Interview Tips to Identify Toxic Cultures
• 10:01 The AAA Method: Assess, Analyze, Act
• 16:19 Empathy in Hybrid Work Environments
• 23:46 Building Remote Culture
• 27:49 Speed Round: Funniest Jerk Stories
• 29:41 Practical Steps to Show Up Better at Work
• 33:44 Empathy as a Powerful Tool

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Flourish: Leading with Empathy - How to Work with Jerks in Healthcare IT featuring Eric Williamson

Sarah Richardson: I'm Sarah Richardson, a principal here at this week Health where our mission is healthcare transformation powered by community. Welcome to Flourish, where we share the human stories behind healthcare leadership because thriving people build thriving systems.

Let's begin

Welcome to Flourish, the podcast that explores bold journeys, brave pivots, and the art of building a career that feels both authentic and impactful.. Today's guest is Eric Williamson, international keynote speaker, executive coach, and author of the Eye opening book. How to work with jerks that I did a review of a couple months ago and it got massive traction, so I'm so excited we get to have this conversation in person known for blending, humor, storytelling, and practical wisdom.

Eric, welcome to the show,

Eric Williamson: Sarah. So good to be with you again. Oh, thanks for having me.

Sarah Richardson: I'm so happy to have you here because you were just on stage at SOAR a couple of weeks ago, and the momentum from having those conversations and those perspectives, I was like, we gotta tell this story more than just the book review.

So what I love is you said you went from expert jerk to jerk expert. You gave so many great stories about that. What sparked that transformation and what did you learn about yourself in the process?

Eric Williamson: Yeah, it, it wasn't easy. It's one of those things where you kind of wish you didn't have to go down that road, but then once you do, , you're grateful for it.

You're, you're taught to study hard, get good grades, and you independently earn these grades. You don't really, it is not like you're working with somebody else. So, when I went to work, I kind of thought that was the same thing I was supposed to produce and. I almost lost my job because I isolated myself.

I was, um, way too cocky, way too arrogant. And I just thought I had it all together. And it wasn't until my boss, he, uh, he made things get real for me real quick, he confronted me and he said, you're not performing, and, and he was like, look, if you don't turn things around.

And I was like, why? Why? Like, people were leaving the job left and right, and she humiliated me in front of my execs. Once I started noticing all these symptoms, I was like, I can't work with someone like this. And it was like extremely difficult. And thankfully, she got what was, what happened to her, she was shown the door.

But I realized that it, that when people are like that, when people leave because of other people. It really inspired me to wanna learn why jerks rise, why they fall, what organizations can do differently. So when I took that experience along with working, being a jerk, it really helped me understand, these kind of workplace behaviors and what you can do differently.

Those are the skills you learn in school, those things you learn in corporations and how important it's, especially today because I'm curious, why do you believe your message. Resonates so strongly now, especially given the state of workplace culture.

Eric Williamson: Yeah, well, I mean, there's just so many things that's going on right now.

I mean, we know what's going on in the news. I try my best to stay away from the news. But even in the workplace, all right, with AI disruption, with reorgs, mergers, all these things go that are going on, it's widen the gap between different people at work, whether you represent business, it, any other department is widen the gap.

And once you understand someone else's perspective, that's where the magic happens. That's where you're able to take those perspectives and inform your own decision and your own thought process about. What to do and it's a refreshing, it's a refreshing thing because once people understand that you don't need to be in those silos, you don't need to, just because you've got all these other things going on, mergers of reorgs, it doesn't replace the fact that you can still be human.

You can still have that connection

Sarah Richardson: You can still be nice, even, you can, even if the stakes are tough and the stakes are high. And in your book you talk about how to spot jerk behavior. What are some of the red flags that from leaders and employees they need to be looking for? What are the things they should be looking out for?

Because you may not realize that it's, it could be pattern behavior.

And those are the ones that you have to watch. So. Some of the patterns that I look for is someone willing to take responsibility? If they never take responsibility for any of their actions, it's always someone else's fault. They're the ones to blame or someone who tries to take your idea. Something like that.

It's the passive aggressive behavior. Like I said before, it's the ones that, that smile on your face, but do something behind your back, and that's what you have to look out for. And those kind of people, they're the ones who don't take responsibility. They try to take credit for your work. All right?

And they try to. They try to they, they try to do those things to, to gaslight you sometimes or to make it do something that you, that you're not prepared for. Because it's not direct, it's not in your face all the

Sarah Richardson: How do you. Plan for that in an interview, or how do you figure that out potentially before you join an organization?

Because there's all the questions that we ask in interviews. We get asked a lot of questions. I tell people, Eric, when you're interviewing for a job, you're interviewing them. I mean, yes, they want your skillset, et cetera but flip that script and be confident doing that because there's things you need to know about an organization before you get there.

Eric Williamson: Right. Yeah, that is an excellent question. I totally agree with you. You definitely are the one interviewing the interview panel. You have to flip the script, especially when you're in an interview. And some of the things that I do, that I recommend especially tech leaders who are interviewing for jobs, they wanna know what the culture is like.

I highly recommend you ask questions such as this, what does success look like for you in, the next, 30 days, what you know what, what are your expectations for me? What is a, what is a busy what. What does a busy environment look like? When you're asking these kind of questions, you're really asking soliciting questions about what the culture is like, how people perform under pressure.

They can't just, sugarcoat it. They can't just tell you what you want to hear because you're soliciting questions that really make them have to answer what that culture is like, what it's gonna look like working with you directly.

Sarah Richardson: And listening for the types of questions they ask. I used to always ask people, how do you handle ambiguity?

Because I knew the organization that I worked in at the time, literally like changed constantly. It was just the way that things got done. We were a big M and a organization that you touched on earlier. Yeah. And you had to realize like your priorities might change every day. Are you okay with that? And, uh.

Things aren't great every single day. You have a method, the AAA method, assess and analyze and act. Yes. Walk me through that method because how can leaders practically apply this framework when dealing with difficult people or situations which happen no matter how great your culture is?

Eric Williamson: Yeah. Yeah. So this is, so when I came up with this three step process, assess, analyze, act, I was trying to come up with a simple three step process that people can follow to help them.

Help themselves when they are engaged in a conflict situation. When something's hitting the fan, when they're encountering a jerk, nine times outta 10. We allow our emotions to get the best of us. We react on impulse. We put our foot in our mouth. We do something that we, but that we might regret.

So sometimes when we're stressed out, like our heart could beat fast, our palms could get sweaty, we get stutter, all these other, all these things are indicators that your body's under stress. So once you're in tune with that, once you recognize that, then you can go into step two, which is analyze Well, why is your body telling you this?

What are you dealing with right now? Maybe you're sick and tired of working alongside this jerk who's gaslighting you or who's egging you on who, or you. You're not having a good performance review, or maybe you're stuck in traffic. By the time you get to work, you're inundated with meetings and phone calls.

Now you can say, you know what, I'm not gonna go there. A much more pragmatic, much more thoughtful response that's not gonna come around to bite me later on. I'm not gonna make a bad situation worse. Here's how I'm going to act. And there's so many times it sounds like a simple process, but there's so many times where people, they ignore steps one and two and they go right to step three and they act and they put their foot in their mouth, they say something that they might regret and it makes a bad situation worse regardless of the conflict situation.

And so you see this in all types of areas. Starbucks, I mentioned it during soar, they have something similar. They're called the latte method and they use that to diffuse 10 situations with irate customers. So there's different methods to help people who are in those conflict situations. And you need something quick and easy to follow because we know sometimes when our emotions get the best of us, all fought, all reasoning goes, goes out the door.

Sarah Richardson: I still wonder how people can get so stressed out over a cup of coffee.

Eric Williamson: Like, come

Sarah Richardson: on.

Eric Williamson: Like

Sarah Richardson: really? Like why is there a lock name method at Starbucks? Like how angry can a customer get over a cup of coffee?

I swear to get, I

Eric Williamson: wanted venti not grande,

Sarah Richardson: I wanted one too much sugar. 'cause they are pretty complicated orders sometimes. I, I, I would, I would, uh, digress so quickly if I totally could on that one. Give us an example though of when you either experienced. Put AAA in action or one one your clients has where the outcome was significantly better because they took those three steps.

Eric Williamson: Yeah. So I was, this is, when I saw this, I was actually thinking about one that happened recently. I was coaching one of my, uh, one of my tech leaders, and she has this star performer who was really like, just steaming the whole team. Like, someone who's got just all the answers and they just dismiss everyone.

She wasn't able, she didn't, come out and just blatantly, demonstrate that frustration. She paused it, she managed it. She did analyze the fact that what was going on around, the surrounding factors, that his behavior, how he was, he was feeling threatened, was because there were reorgs going on.

He wanted to make sure that he was seeing, being seen in a better light that, with these reorgs, are you gonna lose your job or you're gonna get RIFed, or you're gonna go to somewhere else. Well, he wanted to demonstrate that value. She recognized that and that she felt that and she knew that he was doing that because he was feeling threatened and he wanted to secure his job regardless of what happened down the road.

And so that helped and. After that reorg happened, yes, his job was protected. But his performance continued to soar as well. He was able to adapt to those changes, and she was like, Eric, thank you for that AAA method because, hey, without that. I, I probably would've had a, had a mutiny on my hands, who knows?

Would've happened to my job. But she was able to, to really set the stage and to, and to really help that person shift from being able to be arrogant to being able to be someone who can work together with all types of people without having to steamroll of the folks

Sarah Richardson: you bring up.

Such a great point though, Eric, in that scenario.

Everybody has bills to pay, and so that's scenario based understanding of what's happening. That empathy at work that you have emphasized is so important. We've talked we realize we've got social, political, media driven, climate change, in, in our world today. And the thing is, empathy is more important than ever, especially in either a fully remote or hybrid scenario where people think about it.

You and I came outta college ro the roaring twenties, literally like we're unstoppable, but we learned all of our corporate social graces because we were in the office. Yes, and someone said, that is not how you show up, or when you go to this meeting, I want you to observe and write down questions and then come back to me and let's talk about them, because that's how you show up in these different political climates, the corporate politics that happen.

There's an empathy layer, but how do people learn the best way to have these really personal human interactions, if maybe they're not even seeing each other face to face?

Eric Williamson: that is such a, I don't wanna say it's a difficult thing to reconcile, but I will say that there are some challenges with the hybrid work.

And we've been doing this for a while now, definitely at least five years. And for some folks even earlier than that, but one of the things that I've been seeing, especially in hybrid work, that invisible disengagement, where you've got your camera off during video calls or you're, you're just not asking the right questions.

Regardless of whether you're working with, whether it's a, um, a supervisor or manager dynamic with an employee or whether it's team members rethinking the way we do our one-on-ones, because oftentimes when we do one-on-ones, we're doing one-on-ones to ask for status updates on projects and what people are working on.

And, and when we do that, we already know what's going on. Like we've had millions of other meetings. Talking about the same thing, and so what are we doing? We're really checking a box to say, yes, I had this meeting with this person. Yes, they confirmed what's going on with these TPS reports, for lack of better example.

What can I do to be more helpful in your situation? Especially if you're having conflict situations or you're, you're trying to create more synergy with different stakeholders, maybe it and systems, it and business, sometimes they bump heads, there's friction there because they have different priorities.

But when you ask questions such as, Hey, what can I do to help you out? How can I support you? What's draining your energy? What's your win for the week? What are, what's got you frustrated the most about the situation? When you ask these kind of questions, not only do you understand what's going on with the project that you know, that happens by default, but you also are able to connect more with that person.

They'll be much more engaged in the process, in the conversation, and you'll be able to connect more. And once you're able to do that, that's, those are, those are empathy questions that solicit much more engagement, much more interaction with people, and it builds a stronger relationship. So those are the ways that I think that we can do.

Sarah Richardson: I love building in those thoughtful questions into the one-on-one, whether you have it as a template or otherwise. Last question I always ask my teams was, what do you need most from me right now? And you got to know each other as humans in person or otherwise, because to your point, we had the in-office environment.

Well, heck, we also had teams all over the country and all over the world in some of these companies. And so that was already an established mechanism. And yet. Post pandemic, I feel like the divide got wider and you try that much harder with that much more intentionality perhaps, is what you're sharing about connecting with people and really understanding their human environment.

I don't envy the, when people were trapped at home with, with parents and kids and pets and trying to get their work done and everyone's using all the bandwidth in the house. Thank you for referring to the TPS reports. Uh, one of my favorite. Yeah. And you should come in on Saturday. Yeah. If you add the camera, humor, uh, when it, when it matters, it can be helpful too.

Eric Williamson: that's a good question there, because. Here's the deal when it comes to empathy, some people, they have this thought that when you're being empathetic, that you know that it's just so you're being extremely soft, that you're just allowing people to just walk, right over you and you're just, just letting people just do whatever they want.

And that's not it at all. Empathy is. A powerful tool. It's what you can do to move the needle, whether you're trying to, improve someone's performance or improve a product or anything. And so one of the things that you can do to to hold people accountable by using empathy is first do the check-in.

Mm-hmm. I, see that there's an issue going on. What's up? What can we do to work together? To, to to to course correct, right? Because here's how it's impacting the work that you're doing. You're still holding them accountable 'cause they're still responsible for getting the work done and doing it right, but you're still using empathy to show that you see that person and that you see that things aren't going right.

And so that check-in, that quick check-in helps reinforce the empathy, make sure that, that they're being connected with, that they're being seen, but also holding them accountable, saying, well look. What can we do to get you back on track? Because I really want, I, I, I value you and I want you to succeed, and I'm here to help.

But when we miss those steps of just being human. When we miss those steps, that's when all hell breaks loose. Sometimes that's when you have jerks in the workplace. That's how they thrive when we don't hold that accountability. So you can do, you can do both. You can be empathetic and you can hold people accountable by doing those things.

Sarah Richardson: Yep. I'm glad you said it that way because people trust you 'cause they know you're regularly checking in on them. Then when you ask like, Hey, what's going on in your life that's causing you to be late? Miss deadlines not play nice with others. It's not as awkward of a conversation, but for sure you still have to have it.

You have to be comfortable having it. As a leader as well, which is really, really key. So thank you for those tips. But again, when we think about how people create culture and how they connect when there is that hybrid environment, how are you seeing teams engage with one another more effectively?

How do you keep fostering that outside of the Zoom room with 20 people or even just the, the project meeting that maybe has four or five participants? What are some of the ways you build a remote culture?

Eric Williamson: Yeah. I think honestly it's how we leverage. And maximize the time that we do have to connect with people.

Instead of just talking about the work. Dedicate one time a week where people are actually talking, having real conversations about the things that they're going through in life check-ins about what's going on. And you don't have to be an open book all the time. Some people don't want to divulge all the things that's going on with their family and friends and stuff like that.

But when you are able to have just real conversations about, about anything it, it could be about sports, it could be about, how they're succeeding, in the workplace, some of the challenges that they're having. When you're able to have those kind of conversations with people, that kind of lets people puts their guard down.

When their guard is down and they're able to just be a human for a moment and just have a real frank conversation about here's what's working, here's what's not. Hey, I had a crappy day about, today because of this situation. You have to have those human conversations. And those are intentional connections.

Now you're not just, you're being intentional about it and you're not, you're not just treating someone you know, like an employee, like a coworker, they're a person. And I think those kind of conversations are, are things that, that open up doors, open up more trust.

Those are things that, especially those are really effective in a hybrid environment. Leveraging the meetings that are there. But having some ground rules, Hey, we're gonna have a meeting, but we're not gonna talk about work. We're, we're gonna have a conversation about Hey, what are some things that are working for you these days?

Um, having those kind of conversations, those frank conversations, I think are extremely helpful.

Sarah Richardson: They are. And sometimes it helps when they're ad hoc. Other times they kinda do need to be planned, like, Hey, we're just doing a wellness check-in today. Yeah. Or. Hey, let's just have a little team get together, coffee, whatever that looks like.

I used to always tell people Monday through Thursday, my last organization camera was on, like, you were engaged, you were there. We used to call Fridays with no Zoom, faceless Fridays. I was like. I like the name of that and actually I was okay with it 'cause like you can't see my face. Although honestly, most people I would talk to on Fridays would be like, can you turn your camera on?

'cause it's really weird to talk to my computer and just have a blank screen. Yeah. You gave people the choice of them wanting to be able to do that. So many great perspectives and ideas. Are you ready for speed round, Eric?

Eric Williamson: Let's do it.

Sarah Richardson: Okay. Funniest jerk story you've ever experienced or heard in the workplace.

She was like, this person continues to undermine me. And I was like, well. What are some things that you know that, that are happening? And so she was like, I don't know. It's just that passive aggressive behavior. I think they're just come, they're gunning from my job. And I was like, all right, well, let's just continue to monitor it.

So then the next time we met, she was like, alright, I found the blatant action. I was like, well, what happened? This person tried to steal my entire presentation. Tell me more What happened? Not only did the person try to steal the presentation, but when they presented it to the boss, they had the person's name.

On the slide, like the beginning slide and so, so, so the client was like, you see, my name is still on there, so you know, thank you very much for sharing some of the stuff that I did. And so then that person had to adapt at the, they was caught. They were completely caught off guard, called out on it.

Sarah Richardson: Those are some of the stories where you say you can't make it up, and then you can't make that up.

It becomes folklore and you're like, and this happened. You're like, how did that even happen? Though, sometimes that getting caught in action is some of the best ways to coach and to grow others because Often, and people will sweep things into the rug. They'll hide things because they don't want to be mostly embarrassed.

I feel like there's a lot of things that happen inside of corporate cultures. Yeah. And yet, to your point, if it's out there, then you just own it and you learn and you are able to move on. But that's a good one. What's a practical step though, that anybody can take to show up better at work, regardless of your environment?

How do you show up as the best version of yourself?

So that's leaving your ego out, out at the door. And that's one thing I. I go time and time again no matter what, and I always encourage people just to ask that, that kind of question.

Sarah Richardson: For people though that have a level of insecurity in their role, they don't necessarily believe they can ask that question at work.

Like being curious or saying, Hey, tell me more about X, Y, Z, or Show me that they don't wanna know. They don't want people to know that they don't know. How do you approach that? If you're the one listening to this and you're like, oh, I'm kind of embarrassed to say I don't know something.

How do you learn about something you don't know without looking like you don't have the knowledge that maybe you're supposed to have in your role?

That's when you wanna dig in and ask that kind of question, what can I do to better support you? Like, well, you know what I'm feeling, I'm feeling a little self-conscious. I'm feeling I've got some imposter syndrome because I don't want to demonstrate my weakness. That right there, that's the signal right there, is when you want to ask that question right there.

Because that shows that that's gonna, that's gonna help you understand what you can do to get better. And as a leader. Leaning in like that's what helps build the relationship because yes, it is good to demonstrate strength, but you demonstrate strength when you can admit your weaknesses, and that's one of the things that you should do.

Practice that self-awareness to be brave enough to ask those questions.

Eric Williamson: nowadays.

But, but you know what, don't I look

Sarah Richardson: it up on your phone and find out the answer, but like back in the day. So I like to say it was a lot harder to go source some of this info now it's at your fingertips. Write it down if you that

Eric Williamson: ChatGPT

Sarah Richardson: Yes. Well, but then you gotta check every once in a while I'll ask it a question just to see if it gets it right.

I know it's wrong. And I'm like, how does, they didn't know how many times before nine or so the Super Bowl. I'm like, how do you not know this information? I like correct my own chat anyway. Who, who's a leader you admire for their ability to navigate difficult personalities?

Eric Williamson: That's a good one there.

And so I admire that about her. So that's what I'm gonna go with.

Sarah Richardson: I love that you said that because let's be honest, like when we have jobs, we're on the road a lot. We have a lot of demands who's ever managing, helping us manage home? Ha has a tremendous amount of responsibility. And they too, to your point, they have careers, they have responsibilities.

And thank you for mentioning her and a thank you to her for being able to make sure that you are not a jerk. When you show up in, in your environments as well. It's like reinforcing, reinforcing what you stand for and, uh. Tell us though, Eric, in one word, what does empathy mean to you?

That's how you manage conflict. And that's exactly how you work with jerks. You do it through empathy. And empathy is power.

Sarah Richardson: And power for good, which I love Absolutely as well. So much wisdom and everything you have shared today and so much fun. One of the things I love about your platform is that you take something that's very tough for people to admit, recognize, or even want to deal with, and to a degree you make it fun.

Hey, how do you turn this into a constant way that we behave more positively around one another? Versus having me something that's painful every time we see it and hear it, even when we sometimes show up that way. I bet all of us could admit times we've been a jerk, maybe even this week. So if you're listening to this and, uh, either side is resonating, pick up literally a copy of this book.

I love it. You can read it on an airplane ride. And also just flip through for different pieces and parts. So Eric, thank you again for being on the show.

Sarah Richardson: Of course. And Eric Williamson's story reminds us that difficult people don't have to derail our careers or even our culture by learning to assess, analyze, and act.

With empathy, we can transform conflict into connection and thrive even in the most challenging. Workplaces, Eric's humor, wisdom, and practical tools have shown us how we can all show up better For our listeners, if how to Work with Jerks Struck a Chord, grab your copy, share it with your team, and start a conversation that matters.

And if you reach out to Eric, I bet he'll come in and facilitate some of those conversations with you. And as always, keep flourishing.