Create Agile, Inclusive Work Culture, Confidence, and Resilience

Ever had a boss that drove you a little… bonkers?

You’re not alone. In this episode, Adrian Gostick and Chester Elton sit down with visionary tech executive and new author Eric Charran to explore the fascinating world of dysfunctional leadership—and how to rise above it.

Eric’s new book Have You Ever Had a Boss That… breaks down nine archetypes of difficult managers—from the “Firefighter” to the “Amnesiac”—and offers real-world strategies for thriving, not just surviving, under imperfect leadership. It’s a masterclass in navigating workplace anxiety, fostering self-awareness, and transforming chaos into clarity.

🔑 In This Episode

• The 9 boss archetypes and how to spot them
• How to reduce anxiety when your boss fuels it
• Why self-awareness is the foundation of great leadership
• Reframing toxic work environments without losing yourself
• The power of choosing happiness—and when to move on

💡 Key Takeaways

• Quit taking it personally (Q-TIP): It’s not always about you—it’s often about them.
• Know your worth: If the situation can’t change, have the courage to walk away.
• Behavior isn’t identity: Dysfunction often comes from using the wrong tools, not bad intent.
• Confidence is your secret weapon: It’s the closest thing humans have to magic.
• Happiness is a choice: Reframe your challenges and run toward something positive.

🧠 About the Hosts

Adrian Gostick and Chester Elton are bestselling authors, keynote speakers, and executive coaches known for their work in culture, gratitude, and mental wellness at work. Their podcast Anxiety at Work is a must-listen for leaders and teams navigating stress, change, and high-performance demands.

✅ Subscribe & Share

If you enjoyed this episode, leave a review, share it with a friend, or connect with us at TheCultureWorks.com for more tools to help your team thrive.

Transcript

So, have you ever had a boss that drove you, well, bonkers? Yeah, I think we can all check that box, right? Hello, I'm Chester Elton and this is my co-author and dear friend, Adrian Gostick. That's right, Chester. I think I remember a boss that you and I may have had once that yeah, I may tick that box. And our guest today, no names, no names. Our guest today has identified the types of dysfunctional bosses out there, and more importantly, what we can do if we find ourselves working for one. As always, we hope the time you spend with us will help reduce the stigma of anxiety at work and in your personal life. And with us is our new friend, Eric Sheron, author of the new book, Have You Ever Had a Boss That Dot, Dot, Dot? Succeeding in a Dysfunctional Workplace, which comes out in March of this year. Eric is a visionary technology executive and thought leader with more than 25 years of experience in transforming global enterprises through digital innovation, data-driven strategy, and AI-driven solutions. His background includes work at Microsoft and Capital One, where he served as chief architect. Welcome to the show, Eric. We are delighted to have you on the show. Adrian Chester, it's great to be here. Thanks so much for having me. This is going to be fun, Eric. So tell us, in the book you identify these nine boss archetypes. That's quite a few. Walk us through, maybe not all nine, but some of the most common that we probably have all experienced. Yeah, this is a great question because I get questions like, what are the most common? What's your favorite or the most difficult to work with? And I think it runs the gamut. What's interesting about how I kind of came up with these is I just started talking to a bunch of people that I work with and doing some thoughts around looking back at my own career. I've been around a while, so I'm a Gen Xer. My career launched when the dot-com era happened, so been around for quite some time and saw some of these behaviors kind of reoccur. I think like if I go back to that era, when I was early in career, the firefighter archetype, which is the first one I think I introduced in the book, was probably the most common. And the firefighter typically occurs in organizations that are young organizations that are part of a large organization with a division or a department that's rapidly growing. And the mantra, which we call it now, is move fast and break things. Back then it was just, do it as quickly as possible and then we'll adjust in the future. The challenges with that is that in rapid growth, as you and your listeners may know, is that you have to fight fires. You might not have the luxury of having sustained engineering teams or operations teams or standard operating procedures. When you have a system, an e-commerce system and money stops moving, you wake up at 2am and everyone goes into the office and you write code until the money starts flowing again. The CEO comes down the hallway, hats your manager on the back. You're got a great high because, you know, it's kind of like a firefighting moment. You descended from the heavens and put out this flame. And it was great until the next time it happens. And it's less great. And then the next time it happens, and then it's less great than that. And then you start to realize that, hey, we're tripping over the same rock every time. And maybe we should move that rock or do something better. But strangely, what ends up happening is your manager, who's in charge of the resources to fix the problem is kind of like, you know what, I think, you know, the organization counts on us to just fight the fires. Let's just make sure that we're in there, in the operation center, in the trenches, you know, struggling to put these things out. And when organizations start to grow, you know, certainly that fatigues you because you're like, I really don't like failing the same way five and six times. I have a better way to do these things and here's how I do it, but the firefighter manager perceives their value as being able to fight those fires. And as a result, it's a big challenge to get them to change. And you know, no pun intended, but the firefighter does burn you out, don't they? I mean, you can only do it so many times, right? That's exactly right. Now when the organization starts to grow, Chester, on that exact point, when the organization starts to grow, new leaders come in and they're like, hey, thanks for putting out the fire. Is everybody okay? You all work so hard. How do we prevent this from happening in the future? And then that's where you see your manager like, like, who am I if I'm not fighting fires? He's talking about getting rid of fires. I don't know how to survive in that world. You know, love that you've got these archetypes and all that experience. And you know, you probably had a lot of personal experience in your book as well as we all do that write books, right? So walk us through your leadership journey and how you learned from good and bad managers and what lessons you learned along the way. Yeah, it's funny. When I was talking to a couple of interested publishers around the manuscript, they're like, so are you saying there are no good bosses or good managers? I'm like, absolutely not. In fact, most of the managers I've had were fantastic. They were amplifiers. They had the right tools in the toolbox, right? And so I learned a lot from them. But what's interesting, an interesting phenomenon that I kind of realized, and I was a reluctant leader in my career. I was saddled with leadership early. One of the worst things you can do in the tech industry is take a really good developer and make them a manager. And I had that done to me, and I was super excited by the way. But then I realized that I had to deal with performance issues and vacation requests and year-end salary adjustments, and I'm like, bleh, I just wanna write code. So I remained a voluntary individual contributor for the next 10 to 15 years of my career at Microsoft, until a manager who was a fantastic manager came along one day and said, Eric, you have done a great job of going fast and everybody knows you can go fastest alone, but I need you to go far. And to do that, you need folks to help amplify that you can scale through. So I made the mistake of hiring people like most early leaders do. I hired people that were exactly like me. They talked like me, they had all my strengths. They, I said, I just need to make more of me and then that'll be better, right? And it turned out for a short time it was until we all failed the same way. We all had the same blind spots. And so I learned that leadership lesson early. But also what I learned is that you need to be self-aware. Like some of these challenges that I've seen, these challenging unhelpful behaviors I call them, which show up in people. In the book, I try to separate the behaviors and the behaviors are what the archetype is, not necessarily the people, because the people just happen to have screwdrivers when they need hammers, or they just have the wrong tools in their toolbox and they get those tools because they look at managers who have led them. And they're like, oh, well, this is how you lead. You kind of shout at people when things don't go well. You just react, you make decisions quickly. You don't have time to go dive into the weeds and get a bunch of data to make a quick decision. You need to seem decisive and you need to spring into action. You need to save the day. You need to deliver results and then you need to make sure your team is happy. And so these managers today are under such intense pressure and I felt that. And one of the things I focused on was trying to not repeat the mistakes of the past. It's kind of like, hey, I'm not gonna be the same type of parent that my parents were in this circumstance, right? It's a very similar kind of self-awareness. And that's kind of where my leadership journey allowed me to kind of identify some of these recurring behaviors, and oddly enough, recognize them in myself, and then try to make sure that I didn't actually repeat the cycle because these behaviors persist in silence when people have to suffer through them. Yeah, it's such a, I mean, there's so much to unpack in there about what managers do and the sort of the tendencies we fall into, we haven't been trained on this so much good in there, but what if I'm an employee working for one of these managers, you know, maybe somebody, you know, I'm sure you know, that some of your archetypes are more toxic, some are more clueless, you know, well intended, but not communicative, not appreciative, etc. So what if I'm working for one of these bosses that may isn't really meeting my needs? How can I especially our podcast is anxiety at work, how can I get my anxiety levels down when I'm not getting the support I need as an individual contributor? Yeah, it's so frustrating. What a great question. To me, I outline across all of these archetypes, I try to create a structure, which is let's kind of ensconce ourselves in the challenge, in the emotions that come with the behavior, the unhelpful behavior. And then I try to talk about why is that, why would a person choose to behave this way? And the answer is that they really wouldn't if they had the choice in many circumstances. Then we kind of empathize and use emotional intelligence to be like, what's it like to sit behind my manager's desk? And then we figure out, well, how do we actually grow the manager? Not only do I want to cope and survive, I want to thrive. So what can I do? What am I empowered to do? Am I powerless? Do I just have to do what Eric did early on in his career when there was no such thing as bringing your whole self to work and psychological safety and belongingness in the workplace? It was just, if you're getting shouted at, you just deal with it and you'd say, you know, got it, I'll do better next time. And the way that I kind of try to frame this, regardless of what the archetype is, is I try to frame it in terms of what is it, what is it like, what's the behavior? And you have to get over the injustice that you experience. So I think one of the archetypes I write about was the amnesiac, which is no matter how much prepping that you do for your manager, no matter how many emails, slacks, Teams notifications, invites that you send to prepare for a high stakes meeting, no matter how much you do that, it doesn't go from RAM to ROM, right? It doesn't go from short term memory to long term memory. So your manager will show up in that high stakes meeting where you're trying to convince somebody or present something, and they will be like, why are we doing this? Who invested in this? What's the budget? What's the value in this thing? I don't really understand the value. And you're like, you are just deconstructing everything. It's like I didn't even, so there's that frustration, like how can you do this to me? And one of my managers, and I'm sure this is a common saying, said, hey, you have to practice Q-tip, which is quit taking it personal. It feels like it's being done to you because of who you are, but it's just this manager, it's their challenge. And once you're able to get over the shock, awe, and just the toxicity of that emotional reaction, and you can say, well, let me try to figure out why this person is doing this. I'm sure if they wanted to remember, they would choose to. They probably can't for a number of reasons. And then the question is, well, how can I help them? Obviously, what I'm doing to help them prepare is not working. There's got to be some other techniques and tactics, which I put in the book, to help with these archetypes that can help people manage upwards and kind of manage their manager, if you think about it that way. Excellent. You know, I like your labels for these archetype managers, the amnesiac. The one that jumped out is the emergency broadcaster bus. I'm old enough to remember, you know, when there were only a few channels and every night we'd go, eeeeee, we're testing the emergency broadcast network. And so whenever I hear that, I go, oh, so do we have a fallout shelter, Dad? You know, is that the plan? So tell us about the emergency broadcast bus and how you deal with one of those. Yeah, that's a, it's a, it's a great one because anybody that has had, whether you've been an executive or you've been early in career, you get these 7.30 a.m. meetings that pop up on your calendar from your manager. And the reason why they pop up at 7.30 is because your boss has woken up and has received a Slack message and or a Teams message or an email or a call and they're like, hey, this meeting is today. Five states meeting, C-suite level meeting, you have to show up and this is what I expect you to talk about. And they have their heart drop through the floor because they're like, I got no context. I don't know what this is. All right, everybody get together, all hands on deck. We need these slides. Who's gonna talk about what? And by the way, I know that I can't probably disrupt their packed schedule. You know, as executives, we all have schedules from like, you know, every five minutes is accounted for, right, throughout the day. And so, well, when's the time that I know that people aren't busy? It's either really late in the evening or it's super early in the day. So people show up on the Zoom, they've got kids screaming in the background that they're trying to drop off at daycare, people are getting on and off trains, they're juggling their phone with their Starbucks cup, and it's just a terrible way to start the day, especially when you have done everything you could possibly do to prepare your manager with the context that they needed already. And you're just on this call saying, nope, I sent you this last week. Nope, search your email inbox. Already provided to you. And it's just a matter of that manager not having the bandwidth time to have had stored any of this information in their long-term memory. And so the panic allows them to, or incites them to have this emergency broadcast. Everybody hop on the phone at 7 30 and make sure I'm up to speed. Yeah. Yeah. I think we've all worked in those kinds of, right. And they're just draining. I, I was doing a three 64 boss yesterday. We do executive coaching. And that was one of the things that I heard from one of his people was that we got to stop these, you know, you need this tomorrow or we have to have it Monday and it's Friday afternoon. So there goes my weekend. You're exactly right. So how do people learn more about your work, Eric? Where would you send them? You can connect with me on LinkedIn. So you can kind of, I post things there. I have a couple of technology shows I do on YouTube where I talk about different elements and aspects of technology. I'm doing a bunch of shows much like this to talk about leadership. You can connect with me on Instagram, author Eric Charon. Same on TikTok for as long as that's gonna be around. So I'm there too. And yeah, I'm looking forward to just hearing what folks think about the book and whether they think it's been valuable. Oh, this is, no, it's an exciting time because we're talking with Eric right around launch time. We've been through that dozens of times ourselves. And yeah, we know the excitement and the anticipation of launching. So yeah, we wish you the best of luck with the book. So give us some thoughts, Eric. I mean, you've had a good, I mean, really illustrious career working for big organizations. What did writing the book teach you, maybe that you didn't know before? Give us something that maybe you, was a bit of a surprise as you went through this process. Yeah, I think I touched on it a little earlier in that, you know, I consider myself to be a self-aware individual, but if you are truly self-aware, then you know that if you think you're self-aware, you're probably not as aware as you think you are, if that makes sense. And that's what I experienced as I was writing these books. Like, you know, one of my own discoveries is that I have a little bit of the amnesiac in me. I'll ask people to do things, they make total sense, and then I'll forget, and then I'll ask them again, and then I'll ask them again. And I'm trying to get better at that. My growth pattern is, here's my failure, everyone. Just to be aware, this is something I'm working on. If I ask you things twice, it's because that I forgot, because I move so fast, my brain moves so fast, that I think about things in the moment, and I don't write them down, and I need help. I need a chief of staff in certain circumstances, or I need a program manager to help me track all these different dates. So folks that have worked under me, that's probably the number one thing they'll say. They're like, well, hey, it seems like you're writing about yourself in this one. In many instances, I was. And so as I was writing the book, I'm like, gosh, I probably do this too. I probably forget things and make a quick decision. And it's probably the right decision in the moment and that I don't remember that I made that decision, right? So it's a challenge. Maybe there's some good there. Maybe, Eric, if I work for you and mess up, maybe you forget that. Is there some good in there? Yeah, there's always that chance, Adrian, but I forgot what I asked you to do, and if you blew a deadline, maybe I don't remember it. That was Chester. Yeah, it was totally Chester. Well, I was going to say, if you need a good coach, Adrian is available, Eric, to walk you through. I'll take all the help I can get, absolutely. Hey, listen, let's get back to anxiety at work and finish up with that. How can our listeners and leaders and individual contributors, right, work together to create that environment with more optimism and hope? I think it's all about recognizing when you are at the precipice of going into that jaded downward spiral. When you wake up before your phone goes off, your phone alarm goes off in the morning, you're like, ugh, it's Wednesday. You know, there was a point in time where, I often say that happiness is a choice, in most circumstances, and for most people, I'll say. And so you get to choose how you frame these challenges. Instead of saying, oh, I have to deal with this, here's what I get to do today, and here's what I can do to shape how I'm going to have a great day. One of the things that you can do is to recognize when you feel like you're powerless, where you feel like you just have to suffer in silence. And the advice that I would give is you don't. The challenge is, you know, how do I get the confidence to take control, to look at it in a different perspective? How could I engage in positive, you know, positive mental thinking and adopt a positive mental attitude, no matter how adverse the situations and the challenges and the unhelpful behaviors are. And what do I get to control and do? And how can I adopt a set of tools of my own in my toolbox, which actually become the tide that lifts all boats, my tide and my manager's tide, or my boat and my manager's boat, rather. And I think that those are the, I think that's the best way I can think of to talk about like resiliency. Resiliency used to mean, hey, if you get shouted at by the boss, you get reamed out by the boss, you just go back to your desk and you take a deep breath and you work harder. But again, I think as I said, these behaviors thrive in silence. So the closest thing that I think that human beings have to magic is confidence. But confidence is a tricky beast because how do you get it? Well, you just have to have it. Or how do you manifest confidence? Do you fake it? And then when things seem to work out, then confidence is there. Either way, the underpinning is know your worth. Even if you were to read this book and try to practice all of the techniques for every archetype, it still may not work out. And in that scenario, you have to say I'm throwing good energy after bad. And I know my worth and I'm not gonna stick around. You know, some of my mentors and leaders in the past have said that people don't quit organizations, they don't quit teams, they quit managers. And I completely agree with that. And I think you should, you should say, I'm in a burning house, but I don't wanna run from this burning house into another burning house. I wanna run towards something, right? And before the house is on fire, you feel like it's on fire. Make sure that you make the choice to run towards something positive. That is excellent. Great advice, I love that. Know your worth and reframe your challenges. You know, we've heard that before, but it's so powerful to say, you know, I loved what you said earlier, is get over the injustice, reframe this, but know your worth. You don't have to put up with this forever. Either change the situation or get out of Dodge, but do something. Just stay in the same situation. So powerful. Eric, we want to thank you so much for joining us today. Again, the book is Have You Ever Had a Boss? That dot, dot, dot. It comes out this month, so please pick up a copy everybody Eric We want to thank you so much for being on our show today, and we wish you the best of luck with the book Actually, it's been great Adrian have you ever had a bad boss? Of course we've all had bad bosses a curious as to what your takeaways are yeah Cuz you know you and I are thinking of the same bad boss who I don't even know which one of these he sort of fit many of these archetypes. But yeah, I love the firefighter. It just kind of always, he jumped in there because I hear this a lot. And I said I was dealing with it just recently with a boss that we're trying to coach and help. And you know, once to, everything's 911. It's like, or 999 in the UK. And everything's an emergency. And I'm going to put the meetings in the morning or the evening because I know you'll have to be there. Well, not everything is an emergency. And I love that idea, like we keep tripping over the same rock. Fix it. Dig the rock up. Yeah. I do love the titles of his guys. Yeah. Amnesiac. You know, the boss. No matter how much you prep him, no matter how much information you give him, it's going to... So are you sure you sent that to, what was the subject headline? What do you mean I already have that report? I would have seen that. And of course, the idea of that boss is, look, I'm just so busy. I'm just so important that you need to follow up with me. I did love the emergency broadcaster guy too, which was always great. My biggest takeaway though was the Q-tip. Interestingly enough, quit taking it personally. You know, it reminds me of the old Saturday Night Live routine, you know, they'd interview the executive, and it's him, right? It's not me, it's him, right? It's not me, it's him. And you just realize that it really isn't you, it really is them. No, and I love that too, and I underline that as well. Now it's easier said than done sometimes, and you know, but, and he's exactly right, because he's been in these situations for, you know, 20 years at Microsoft. You go into a meeting, you're presenting all your stuff, you think you're brilliant, and then somebody says, why are we doing this? This is stupid. And they start picking apart your work that you've been working on for three months. Quit taking it personally, your paychecks still go through, it's not about you. Now, if you're in a constant chronic situation where that's happening to you all the time, that's where you're tripping over the same rock. But for the most part, we do have to realize, I still have worth, my work has worth, but they pay the paychecks. This is what Marshall Goldsmith, our mentor tells us, is look, the person who makes a decision, makes a decision. You gotta get over it and you gotta move on. And it's hard sometimes. Yeah. Last one for me is, he said something my dad used to say all the time, he goes, happiness is a choice. Yeah. You know, choose to be happy, control what you can control. And if it really gets bad, run to something positive. I love that. I mean, don't walk, run. You know, the old. I like that, I'm gonna write that down. Yeah, run to something positive. I think that's really good. Yeah. And choose to be happy. You know, you know, I, I, there's something positive in our lives, Jester, and I'm wondering if you could figure out who it might be. You know, it's so funny, it always comes back to the same person. And I think if he weren't in my life, would my life even be worth living? Of course, we're talking about the infamous, go ahead, Adrian. Brent Kline, our producer. We want to thank Brent. The magic. Yeah. We want to thank Christy Lawrence, who helps us find amazing guests and keeps us on track and all of you who listened in. If you like the podcast, share it please and we'd love you to visit thecultureworks.com for some free resources to help you and your team culture thrive. And we love speaking to audiences literally all over the world, right? Virtually in person, hybrid on topics of culture, teamwork, resilience. Give us a call. We'd love to talk to you about your event and please pick up a copy of the book Anxiety at work one for you one for a friend Really some great tips in there and it is so interesting Adrian You know you and I go speak and we say what would you like us to speak? You know about culture and gratitude and so anxiety is always there. You know I help us with that It's it's it's really high on our list so give us a call. We'd love to speak at your event Yeah, I've never been a place where they say you know we're pretty good with anxiety. That one's pretty good. We're actually too calm here. There's nothing going on. Yeah. Hey thanks everybody. Great, Jester, great to be with you and thanks big thanks to Eric Charon and and until next time everybody we wish you the best of mental health. Thank you.