The 9 Signs Your Boss Is Destroying You (And How To Stop Them) - Eric Charran

16 Dec 2025 · 54 min

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TruthWorks Podcast Episode Notes

Episode Title

The 9 Signs Your Boss Is Destroying You (And How To Stop Them)

Guest

Eric Charran Host: Jessica Neal Release Date: March 19

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Episode Summary In this episode of TruthWorks, hosts Jessica Neal and Patty McCord dive into the complexities of workplace leadership with guest Eric Charran, Chief Architect at Microsoft and author of *Have You Ever Had a Boss That...?*. They discuss the nine archetypes of dysfunctional bosses, the impact of these behaviors on employees, and strategies for navigating challenging workplace dynamics.

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Key Concepts

  1. Nine Boss Archetypes
  2. Eric introduces nine archetypes that characterize dysfunctional leadership styles:
  3. Attack Sub: A boss who undermines from the shadows, often invisible until they need something.
  4. Firefighter: A leader who thrives on crisis management but creates a cycle of chaos.
  5. Others include various dysfunctional behaviors not explicitly detailed in the episode.
  1. The Dynamics of Bad Bosses
  2. The conversation explains why bad bosses exist and why employees tolerate them, emphasizing systemic issues in management practices.
  3. Eric shares his experiences and insights on leadership styles that perpetuate dysfunction in the workplace.
  1. Employee Strategies
  2. Managing Up: Employees are encouraged to manage their relationships with their bosses, providing context and support to help them succeed.
  3. Curiosity and Empathy: Understand the pressures that drive a boss’s behavior to foster better communication and teamwork.
  1. Leadership Insights
  2. Good leaders should practice self-awareness and be willing to admit their limitations.
  3. Providing context is essential in leadership; it helps teams operate more effectively and feel valued.

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Episode Highlights

  • Understanding Boss Behavior:
  • Eric discusses how many bosses replicate the leadership styles they experienced, emphasizing the need for systemic training for new leaders.
  • The Role of Empathy in Leadership:
  • Both hosts and Eric highlight the importance of empathy and curiosity when dealing with difficult bosses. Understanding a boss's challenges can lead to a more productive working relationship.
  • Advice for Employees and Leaders:
  • For Employees:
  • Process emotions and understand that many behaviors are not personally directed at them.
  • Cultivate curiosity to learn what drives their boss’s behavior, which can lead to constructive conversations and improvements.
  • For Leaders:
  • Provide context and clarity for your team to ensure they understand their roles and the stakes involved.
  • Actively seek feedback and create an open environment for discussion.

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Actionable Tips

  • For Employees:
  • Develop a thick skin but work to understand the root cause of your boss's behavior.
  • Engage in open communication with your boss about expectations and needs, aiming for collaborative solutions.
  • For Leaders:
  • Regularly check in with team members to understand their challenges and how you can support them.
  • Be open about your strengths and weaknesses as a leader to foster trust and transparency.

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Conclusion The episode emphasizes the critical importance of understanding dysfunctional leadership dynamics and encourages both employees and leaders to foster open communication, empathy, and a proactive approach to workplace challenges. Eric Charran’s insights and strategies provide a roadmap for navigating the complexities of office relationships effectively.

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Further Resources

  • Book: *Have You Ever Had a Boss That...?* by Eric Charran
  • Social Media: Follow Eric on [Instagram](https://www.instagram.com/authoreccharron) and TikTok for more insights.

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These notes provide an overview of the episode's focus on workplace culture, leadership challenges, and practical advice for those navigating organizational dynamics.

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Transcript

Automatic transcript. May contain errors.

0:00The raw nerve is somebody that is just so distracted that anything that happens, they are just like, I gotta react to it. But it's also puzzling because they can just turn on a dime and betray you in a meeting.

0:15What would happen if we just told the truth? Welcome to TruthWorks, where we dig into the nitty gritty of leadership and work. And what needs to change? I'm Jessica Neal. And I'm Patti McCord. Our journey together started in HR, but trust us, it's evolved into something wild, honest, and well, a bit rebellious. So throw out the handbook. We're here to redefine rules to work for us, not against us. Let's dive into another episode.

0:53Okay. Hi, everyone. Welcome to another episode of TruthWorks. I'm Jessica Neal, your host, and Patti is coming back, I promise. Hold on. She'll be back. But today I have an exciting guest. I'm so excited. I'm going to kind of set it up here, but everyone has had a bad boss. Everybody. We've all had them. But we don't understand why they act the way that they do, why they're bad. And it's just miserable, honestly, having a bad boss. But my guest today knows all these things. He knows why they're bad. And he's unpacked it and he's studied it. And he exposes this so that all of us can learn from it and know what to do and how to navigate things when we have these bad bosses.

1:44So my guest today is a fabulous human, Eric Charon. He's here. He's going to tell us how to handle bad bosses. Hi, Eric. Hi, Jessica. Thanks so much for having me on. I'm excited to be here. Yeah. Well, first of all, tell us your story. Like, how did you get into all of this? I'm guessing you might have had a bad boss or two. I'd probably have had a few challenging bosses, definitely to be sure. So for your listeners, I've been around for a while. I'm a Gen Xer. I started my professional career maybe late in the 80s, mid 2000s. I really started, I got going. And this was before like bringing your authentic self to work in terms like psychological safety.

2:25Those things didn't exist. and so at that point in time and the the challenge was that sometimes you got a really fantastic manager that gave you energy they amplified your what you did fostered a sense of team was that coach and then more often than not you actually had bosses that would scream at you and yell at you and just give you you know terrible work but they didn't feel like doing and didn't really think about growing you because they had numbers to hit financial goals to hit and so you developed a thick skin or you didn't. And then you said, this working world is not for me. I'm going to go do something else.

3:00But for those of us that stuck around in the corporate world, the goal was, you know, you just, if someone's yelling at you, you just take a deep breath. You try not to take it personally. It feels awful personal. And when you're a new college grad, because nobody prepares you for this when in your business undergrad or even your MBA, there's very, very, very little, at the time, there was very little corporate culture. And, you know, here's how you navigate professional relationships interpersonally. There was none of that. So you just basically suffered a bunch until you got to a position in which you were in charge.

3:34And then you're like, hmm, well, how do I actually be a leader? How do I do this? And you're like, well, my old manager used to yell at the team when they messed up, when they failed. So I guess that's what I should do. And so this led me to really understanding early on that this is systemic. like leaders lead how they were led so there's a story i tell or in this area even when i was writing the book i thought about this it was like my son he's a student athlete and i said your job is in life for all my kids just to be better than i was so he was he's a he was a fantastic high school student athlete played football did a whole bunch of stuff took ap courses honor roll all this kind of stuff but when i was watching a practice i saw the coach you know the line messed up they jumped and so he's like everybody the offensive line run a lap and that to me was unbelievable because instead of coaching the person that actually didn't do the right thing it's the everybody suffers because you messed up I got to humiliate everybody and if you really don't want to mess up you don't want to mess up because now you know the stakes right now everybody's going to get punished and that was such an antiquated way of coaching but that coach coached how he was coached.

4:44And that led me to this realization that leaders lead how they were led. So that's kind of my story. Like in some ways, parents parent how they were a parent. Exactly. Until somebody, I think every parent might say, I'm never going to be that way, but it's tough when you're in it. Like it's tough when you're actually got, the stakes are high and you have no other tools in your toolbox. Yeah. That's so fascinating. So where, like, tell everybody kind of what, what you did professionally? Like what was your career? So my, my first substantial position, I bounced around the consulting industry and information technology.

5:18I came out during the dot-com boom back in the late nineties. So if you could write HTML, you could write your own, you could write your own ticket. Right. So I kept my business degree because I knew that being able to talk to business stakeholders, but also be a trans, a technology translator was, would be invaluable. That didn't pay off until maybe like 10 years later. Going through that process of coming into the workforce, you know, transitioned into Microsoft in 2005, worked in the field for about 10 years there, worked my way up to chief architects. My role in the field was to basically help people adopt Microsoft technologies around the world.

5:57So these were global customers. So I was traveling to AsiaPAC, LATAM, NIA, North America, all over the world. And my goal was to try to get people to do the same things the same way with quality, move to Azure engineering, which is a component of Microsoft and did look after architecture there for a while as an executive, then moved to Capital One because I had been everywhere in Microsoft. I've been to Windows. I've been to Office. I've been to R &D. I've been to the field and sales and engineering. And I'm like, I don't really want to go backwards. And then a bunch of people were like, well, why do you want to go work for a bank?

6:30Even the CEO who I interviewed with, He interviews all the VP candidates. And he's like, why do you want to come to work here? You're coming to work for a bank. And I liked what Capital One had in terms of financial inclusion. Their motto was change banking for good. It's like a double meaning. Yeah, yeah. And I really found that empowering for underserved communities. They hired really well. I don't know if they still do, but back in the day, they hired really well. Their recruiters are top notch. I talked to them for maybe like six to eight months before I'm like, I'm never leaving this place.

7:04And then all of a sudden I'm like, maybe I should leave this place. So they did a good job. Did a whole bunch of work for Capital One around artificial intelligence and real-time fraud detection and analytics. and then moved to Intuit, where I currently look after architecture, engineering, and mostly products for our underpinning data platform. So I had an opportunity to be an executive leader at those executive levels and really take an introspective look at what really makes a great leader. And the book came about because we were all sitting around one time, me and a bunch of other VPs, we were all just complaining about our managers.

7:44And all of a sudden we were like, hey, I've heard of that behavior before. I've seen this before. I know what's going to happen next. Did they say this? And they're like, yes, that's absolutely what they said. And I'm like, that person is motivated because of these reasons. And then here's what you do. Here's how I survived it. And then so we started giving them these funny little names. Somebody was like, hey, you should write, somebody should write this down. This would make a great book. And then so I said, you know what, I'll do it. And that's how the book came about. That's so fun. So tell everybody the title of the book the title of the book is uh have you ever had a boss that dot dot um you know surviving in a dysfunctional workplace yeah and everybody has had that boss and that's kind of how we came to that realization no it's like when i saw the title of the book i was like that's perfect because everybody's had a boss that dot dot dot something right you know and so okay so you're sitting around the table you're like okay i'm gonna write this book but writing a book is really hard.

8:37Yes, it is. Yes. I'm actually sort of in the process of writing a book right now. Congrats. Thank you. I haven't really said it out loud, but it's hard. It's hard to find the time to do it. And there's research that has to go behind it. So you guys have this idea of kind of hanging around the table, complaining about your terrible bosses. And then how did you actually do the research for the book and write the book? And you came up with like the 12 dysfunctions. How did that all happen? We did a lot of research in terms of like psychology, motivational behavior. Now, it's important to note that I'm not a clinician, but I had the benefit of working with somebody that was as I wrote this book.

9:18And one of the things that they that I wanted to to kind of posit is that the people that exhibit these behaviors, they're not bad people. In fact, if you ask them if they'd rather be a great, inspiring leader that people love to work for or somebody that pounds their fists on the desk in order to get results, many people would want to do the former. The challenge that these folks helped me realize is that they just have a toolbox full of the wrong tools. And the only reason they have these toolboxes full of the wrong tools is because when you start becoming a leader in many of these organizations, they don't actually train you.

9:55They train people like me, which are like senior leaders. They send you to conferences and they give you all these, you know, high powered executive consultants who will help you understand leadership techniques because we're managing, you know, hundreds to thousands of people. But where the real infusion, if you want to change culture and create great leaders, is at that middle junior to middle management level, because these are the people that have no recourse other than to emulate what they saw worked. And if they were lucky enough to have a great manager like I was, then you have the opportunity to say, I'm not going to be like that.

10:28I'm going to be more like this person. And my hope is that everybody gets one of those people in their career in which, you know, you wouldn't have achieved the heist of which you've achieved without them. I have maybe two or three of them, but I learned so much from them. They filled my toolbox with the right tools. And I had the opportunity to discern between those tools and the wrong tools. But that was because where I was fairly senior, that's why I was at Microsoft. but people that are just stepping into leadership because they think it's that next level that, you know, the organization thought enough of me to promote me.

10:58And now I have a responsibility to meet requirements and get things done. Those are the people that are like, well, what do I do now? Well, I got yelled at. So now I got to yell at people. Yeah. Yeah. And I think, well, I want to know what you think about this, but I think a lot of companies promote people because that's like the way to make more money and the way to get value in the organization is to become a leader. And many people are not going to be great in that role. And they don't even really like it, but they want it because they want to make more money and they want to grow in their career.

11:33And that's literally the only way they can. And I think businesses do a big disservice to that. It happened to me. Yeah. You were great at engineering and they're like, okay, let's make them a manager. Same thing happened to me. I was great at recruiting. Right. That's how I started out in the world. Then it was like, okay, let her, let her, you know, run teams of recruiters. And, and, you know, I did, but, but I think the, the other thing too, is like businesses aren't, they promote upon the craft. right and then they're not really digging into can they inspire can they lead can they hire can they fire they develop people yeah they don't they don't do any screening around that they you're correct yeah he's he's great she's great put her in the role exactly they they take whatever your craft success is and they incorrectly extrapolate to say that oh it's time to make them a leader and they're going to be a great leader.

12:37There is a function now. I think every organization has some sort of survey. We call it the pulse survey where I'm at now. I think we call it the pulse survey where I came from. So they can instrument to determine if you're doing a good job leading among all those vectors, but they don't actually invest ahead of time to give you the skills and the tools you need so that you can have great scores. So typically what happens when you come back as a manager or a new manager, for those of you that don't know, you're going to get a score and the score is going to potentially be either fantastic because you are a natural leader or you're going to get a score that's like, wow, I have a lot of work to do.

13:11The people that work for me, they don't really enjoy working for me at all. And so that's going to be, so they're, they're measuring it now, but the next step I would hope is that they will prepare you for it and set you up for success. Yes. Well, we're going to, I want to get into that in a little bit, but I want to talk about bad bosses. Like what, tell what was the most terrible boss you had? Let me hear. Yeah. So let me, let me follow the advice of the folks that advise me in this book to say that the people are not necessarily terrible, although there are some terrible people. There are terrible people, but most of the time I would say they're not terrible.

13:49They're terrible bosses, but shit's running downhill. Yes, it always does. And who's going to get it? Not, you know, the team. Yeah. Right. And I'll tell you this, the most inspiring and the most beneficial manager I've ever had displayed terrible, terrible, I guess, you know, behaviors. And you asked like, what's the most challenging I've had to deal with? It actually was a fantastic boss that was responsible for a lot of my career velocity. I think at Microsoft, I got promoted every two years and it was because of hard work, but it was also because of a manager that really believed in me. But this manager at the time, I call it in the book, I have these nine archetypes.

14:32And this one is called the attack sub. So the attack sub archetype is somebody that runs silent and deep. Emails never reach them. Slack messages never reach them. Text messages are never, you know, never answered. And then they surface at the last minute. And they're like, hey, I got a big assignment from the top. We have an executive board presentation. I need Eric, I need you to create slides. I'll meet, it's going to be in Vegas. I need you to be there on Thursday and I'll meet you right outside the room. And then I'm in an airport, you know, I'm, I'm prepared. Like, and so this behavior is also very difficult because I spent a lot of time doom prognosticating and try to make life easier for myself in the future.

15:09So all of my work and my slides are locked and done before I even get on the plane. So I'm watching movies on the plane, right? I'm relaxing. And then as I'm boarding, this, this exchange comes through and I'm like, now my entire trip has been blown up. So I am like asking all these follow-up questions. Well, who are we presenting to? Which board member is going to be in attendance? Who's asking these questions? How many slides? How much time do we have? What's the core message we want to drive? I think it should be this. They've submerged beneath the waves. You never hear from them again. And so now I am in space.

15:39And as a prepared person who likes to be kind of buttoned up. You're freaking out. Yeah. Yes. Yes. The first time this happened, I was effectively freaking out. I'm like, what on earth would cause you to just deliver that and not understand that I need more details to be effective, especially if we're going to go talk to the board. So I am doing my best. I don't hear from this manager until we are right outside the boardroom. And I'm there obviously early, 30 minutes early. This manager shows up 10 minutes early and they're like, OK, let's see what you got. I'm like, where have you been? I'm like, here's what I've got.

16:10And he's like, you know, no, no. OK, this was good. No, let's not do that one. And I'm like, the door opens in the middle of this, of that, you know, madcap evaluation and we're ushered inside and I just, I just, I'm good under pressure. You know, I have that gear. And so I am like reading the room as you should normally do. And then I'm looking at my manager and I'm watching their expression and I'm like, okay, they probably don't like this slide. So I'm not going to spend a ton of time on it. I'm just going to move on. So that was extremely challenging. It's like they, they, they go beneath the waters, they surface, they launch a bunch of missiles to blow up your life.

16:46And then they go dark again. Yeah. What is that about though? We all know that person. What is that about? Yeah. Great question. So the motivation and part of what I tried to do in the book is I tried to break down, I use the narrative framework. I think I use this exact example of the book. And then I said, well, here's, let's unpack what's really happening here. Because what you have to learn to do is that the behavior is not about you. You're experiencing it. You're experiencing the brunt of it, but it's a deficiency typically on their part. It's not the right tool, certainly. But that question becomes, well, why are they choosing to use that tool?

17:17They're choosing to use it because these managers, and speaking now from myself now that I'm more senior, we are under intense pressure to deliver results. We are constantly under a deluge of emails and Slack messages and people demanding our attention and escalations. I think the higher you go, the more escalations you have. And as a successful executive, you're really good at navigating through the escalation, lowering the temperature and achieving the result. Well, that becomes very interrupt driven. and as a result when you're interrupt driven the last thing you can do is be like you know what i'm going to give poor eric over here as much information as he needs to be successful instead in this sea of electronic communications and escalations in which you kind of you kind of develop kind of like this you know looking over your shoulder where's the next one going to come from the last thing that you can do is spend time helping somebody make a successful presentation if i know i can counter that person they're probably going to do a pretty good job i've got to go now and take care of all these other people that are shouting down, you know, down at me from above.

18:19So if you understand that that's the motivation, now it becomes, well, what kind of tools can I equip you with? How can I help you? How can I help you triage your escalations? How can I be your go-to person? If you're having an escalation, send it my way. I'll help you with that. If it helps you become more prepared, answer emails, grow your team, and then help your team actually takes some of the burden away. Yeah. So you're saying that folks should have that conversation with their manager. 100%. And in fact, based on my own experiences, I actually model what that conversation looks like in the book.

18:54So certainly not a script you can memorize or that's going to work 100 % of the time, but the hope is that it illustrates the ways in which you can have non-confrontational conversations with your manager. And especially, we used to have a saying in the olden days, which was you need to manage upwards. And it's 100 % true. That hasn't gone away. You definitely need to manage upwards, but you have to do it coming from a position of humility and empathy. If you try to do a constructive criticism, compliment sandwich, those are all great techniques, but that's only when the person is willing to listen to you.

19:26So what I learned throughout my career is that people don't make logical choices. They make emotional ones and then they look for reasons to back them up. And if you're coming in at the last minute, being a subordinate, trying to change your manager's mind, and you have not emotionally connected with them, then they are going to dig deeper into the behavior. And they're going to dig deeper into saying that, no, you don't know what you're talking about. This is effective. So you have to say, this must be tough for you. I can't imagine what it's like having to deal with all these escalations and then prepare for a board meeting.

19:57No wonder you weren't able to provide me proper guidance and to help me. and all of the challenges that I felt you must have been feeling in 10 times over. Yeah, no, I mean, it's so true. And I think I don't know if you found this like in your research, but just me being in the role that I've had to be as like a CHRO and guiding managers and employees through all these things, right? Because it really comes down to like communication. So, You know, I think that there's this symptom that the employee thinks the manager should know what they're thinking and needing. And then the manager also thinks that the employee should understand the enormous amount of things they have on their plate.

20:43And neither of them talk about those things. They're just like, you should read my mind and you should read my mind. But nobody does. And nobody's a mind reader. you know you have you're you're 100 right talk to each other absolutely i am i when i was writing this book as i was going through all the different archetypes i'm like gosh i am probably like i have one archetype called the amnesiac okay it's a forgetful leader so it's a leader that really just doesn't remember anything that they ask you to do so they ask you to do things multiple times i'm like gosh that's that's me like i i do that but to your point like one of the things that i do as a leader is I oftentimes have one-on-ones and skip level one-on-ones with the folks on the team.

21:27And I encourage all of them to just, one of the things I ask is because a lot of earlier career folks don't necessarily know how to use time with executives. And so when I sense that, some of them come really prepared, like, hey, what's your thoughts on this? And I'm working on this and give me your guidance and all that. Some of them are like, hey, Eric. And I'm like, well, tell me about the most important thing you're working on. Or tell me some of the most difficult things that you've had to deal with recently. Tell me why you would love to stay with this team and what can I do? So it's almost like I'm re-recruiting them when I'm talking to them.

21:56Not a lot of managers do that, but you're right. Like, so through those four or five prompts, I really can kind of draw out of them what's on their plate, what's happening that I might not be aware of, what's the pulse of the culture, all that kind of stuff. It's very important. Yeah. You know, I'm glad you said that. I think one of the things that I learned to do, and it took me some time to learn how to do it. But a couple of things that I always try to remember as a leader is that one, it's not about me. It's about them. And my purpose as a leader and my only purpose is to make sure that they have the context they need to be successful, right?

22:34And I always like approach things from that lens and the context thing could be, do they have the information? Do they understand the why? Is it clear? or sometimes it's more of coaching. Like, hey, I saw you did this. Next time it'd be better if you did it this way, right? And if you don't know how to do that, I'm happy to talk about how to do that. Do you want to brainstorm about it? But I think that way back in the day when I kind of learned how to do this, it really helped me become a better leader. And I didn't have to control. I just had to think about context. What strikes me about your story is that good leaders are self-aware.

23:14So in your story, you were aware that you had the context, but that doesn't mean that everybody else has the context and you become a channel to provide that context. I think that leaders, even myself, who I consider myself to be self-aware, but who knows if I really am, but I try to be. Sometimes I have the context and then I just want to hand out assignments. And what could be, I don't wrap the assignments in sometimes is the context. And it's very easy to forget that you have that context, you understand the stakes, you understand all the people that are going to get angry if you mess up or pat you on the back if you do a good job and why you're doing it.

23:50But it's difficult sometimes to step outside yourself and to embody the person that you're asking to help you on your team, to give them an assignment and give them the context. So being self-aware is super important to realize that you have a context, but your team might not. Yeah. And, um, you know, the, one of the stories that I tell is that, um, to read our CEO, I was complaining and I was like, uh, my team, they're not doing this and they're not doing that. They're just horrible. And he's like, well, you know, whose fault that is. And I was like, yeah, there's duh. You know? And he's like, no, it's yours.

24:28If they're failing, you failed. And I was like, huh? And he's like, and the reason why they're failing is they don't have the context to be successful. And it was like one of those conversations that changed me forever as a leader. And I never, you know, approached it the same way. I was never a yeller or, or anything like that. You know, I had this one person and I won't, I won't say who it was, but we were talking about their boss and he's like, yeah, like, you know, he throws stuff at me. Like, and I'm like, like what? Like, he's like, well, books, cereal. I was like, cereal? Physical things.

25:05Wow. You know, so I mean, like, there's, there's that. I was never, you know, I was never a yeller or thrower or anything. I always, I'm more of a coach, but, um, but I think that there are, there are moments in, in your life as a leader where you really learn. Right. And, you know, Generally, it's someone like a reader, someone else pointing something out to you, right? Let's get back to the archetypes for a second. What's the worst one that people need to look out for? I think it depends on who you are. I said my worst archetype, depending on the type of person I am, is the attack sub-archetype.

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25:44Another challenging one for me was a firefighter. And I wrote a Harvard Business Review article about the firefighter. Yeah, let's talk about the firefighter. Yeah. So the firefighter was one of the archetypes that I encountered in the early days of my career. So this is an individual VP senior individual. We were part of a business processing outsourcing company. So this is pre Microsoft and it was my first corporate job. And so I was responsible for being a developer, software architect, engineer on our payments platform. And this individual was an impressive individual. Stern's School of Business educated, respectable VP, somebody that I would definitely learned a lot from actually, but they, that they derived from work, their identity was somebody that could manage a crisis like you've never seen.

26:30They would, when the systems went down back in those days, we were not moving money. That's a big deal to everybody behind. We used to call it the fishbowl where the executive sat behind this glass wall. And so the CEO, COO and CEO would come out along with the CIO and they would come to, you know, this individual's office and they'd be like, what do we do? And he's like, don't worry, I got it. we had this giant network operations center. It was very 24-like, if you remember 24. So we would all go in there and we would be like, yeah, we were like writing code and watching what was happening, you know, with the payments.

27:03And, you know, there was even a time where he used his own personal credit card to, because we had, our cloud provider had gone down and he's like, I just need to set up a new tenant. And he used his own personal credit card. So he was awesome in a crisis, but it was the quiet moments between the crises that really defined this individual. and what led me to really understand that, you know, it was exciting watching this person work, especially as a new employee. I'm like, wow, so we're here at like 2 a.m., adrenaline's flowing, we crushed this problem. And it was great until it happened the next time.

27:35And then it happened again, the exact same way. And I said, well, gosh, I'm still young, I'm still new here, but maybe I can see why it's happening. It's because this piece of code was written in such a poor way, there's no error handling, not to get too technical. But the idea is I'm like, if we can rewrite that code and I can put in the error handling and we can redeploy it, we could actually stop this entire thing from happening ever again. And it's almost like I was talking to two different people. There's the version of that manager that's in the operations center handling the crisis. And then there's this more muted version behind the scenes that is just like, yeah, it might sound like a good idea, but I really need you to work on, you know, you know x y and z and i'm like but if we don't this is going to happen again and then it happened a fourth time we're up to like two three in the morning and i'm like i'm like looking around am i the only person i'm looking at my peers are like no this is crazy we could fix this easily and what i realized again i did dive into my the motivation right so this person what's that about yeah this person feels that their function is putting out fires that's why the organization feels valuable And to the point where they're like, if I'm not putting out fires, what good am I?

28:48I'm not going to get any attention from the C-suite. The C-suite's not going to just show up at my door asking how I can help this out. And so I love the fires. It's rewarding. There's a lot of adrenaline. I get high fives from executives when I'm done. Why would I want to stop these fires? Like, you know, I don't want to be a fire department with nothing to do. But what you really don't realize is that fires leave damage, right? Like imagine if you had little fires in your apartment. no one would, you know, be high-fiving you. Thanks for putting the fire out. They'd be like, okay, how do I prevent these fires?

29:20How do I prevent forest fires from happening? Because they damage people. They damage systems. They damage the organization. So the firefighter was challenging for me to deal with. So that was the motivation. Once I understood, it was all about like, I don't have any value unless I'm putting these things out. We had to switch it. So I said, well, what about we, the new metric is days without incident. How about that? How about you now become the person that prevents fires from harming the organization. And your metric is how long you've gone on this. So in this example, you suggested that to this leader.

29:52Yes, but only after I respectfully said that, listen, I know what it's left to put out these fires. I'm there with you. You know, I'm there with you and I love it. But what's happening to the team, the damage that it's doing, the challenges associated with why people came to work here, we're not there and we're not experiencing it. So I know it's important to put out fires, but I think there's a more valuable way that we can be seen and gain visibility at the executive level. It's days without incident. And we actually got one of those, you know, days without incident notepads from Staples and we hung it in his office.

30:28And that was, and this individual was motivated by, you know, core metrics. It used to be numbers of fires that you put out, number of incidents handled. And now it's days without incident. And that really turned this person around. Wow. The fact that you knew how to do that and got the person excited about it, I don't see many employees doing that. It took a while to get there. So first, what happens when you're in a situation and you're experiencing a behavior, an unhelpful behavior, I'll call them, that you've never experienced before. Like I call a conference room betrayal, right? So there's an archetype that I have, which is the amnesiac or the raw nerve is a good one.

31:16The raw nerve is somebody that is just so distracted that anything that happens, they are just like, I got to react to it. So as an example, pretty much, but it's also puzzling because they can just turn on a dime and betray you in a meeting where you would previously. So in this example, we were trying to move cloud providers and I had done all months of research and stood up, you know, mission teams and did proofs of concept with both vendors. We had arrived at a conclusion and we were about to present our evidence to this chief data officer. And my manager at the time was like, you have everything you need.

31:53I'm like, yes. So here are the first points we're going to hit, second points, third points. That was Friday. Meeting was on Monday. We're in the conference room. Everybody files in. It was in person. which was rare back then we start presenting and then my manager leans back and they're like yeah I was on Reddit yesterday and I read this platform people hate it and this person on Reddit was really trashing it so I'm not sure if this is the right thing for us to do Eric like what's happening you're supposed to be in my corner supporting this you know the work we've done and all of a sudden a Reddit post just hit a nerve yeah and change their mind no data underneath that post that's just an anecdote a minority anecdote story that they read on a social media platform over the weekend right by the way no they also talked to their neighbor who was in the business and they're like yeah perfect so that's two two sources out of the entire empirical evidence body i gathered now the reason i'm telling this story this is the raw nerve archetype i write about in the book but the reason i'm telling this story is i had i didn't have the tools to i just felt wronged i felt betrayed I felt why would you do this to me yeah and what what does that say about my relationship with you like maybe there's an alternative means that you're just trying to make me humiliate me make me defend you know or maybe this is some kind of weird trial you're putting me through or some some weird test I didn't really understand it and so I didn't say anything after that meeting for a while because I was so what do the kids say in my feelings right yeah so but what I what I really had to understand was that this was not about me as an individual.

33:31And sometimes that realization is challenging for early in career folks because it feels personal. The embarrassment, the betrayal, the, you know, having to scramble. And I did a pretty good job. I'm a pretty good, you know, scramble quarterback when I need to be, but I was just perplexed is really after I stripped away all the negative emotions. I'm like, what is this? And so, yeah. So you're saying like how rare it is for early career folks to have that gear, find the curiosity, find the motivation. So you have to go, you have to process your emotions and feel your feelings for sure. But after you've done that, try to understand why they're behaving that way.

34:08So this leader is got the attention span of maybe like a squirrel, right? And so, and sometimes - That movie up the dog squirrel. Yeah, exactly. And then sometimes in reality, that's not to say they're any less capable or any less intelligent or any less deserving of the position that they're in. But in reality, like if you dig down deep enough in that example, they're just nervous about making a recommendation. They're trying to, and it's coming out and leaking out in all sorts of weird ways, right? And so they're trying to kind of sabotage their project, which I'm leading ahead of time. It's almost like pre-failing.

34:46So that they can be like, I knew this wasn't going to be a good idea. Right. And so that's kind of what, once I understood that I said, well, let me spend some time with you. Let me, listen, I know this is a big decision and it feels like if it goes wrong, it's going to be laid at your feet. But if we open up our heads and tell everybody what our thought process is and what, you know, fueled our decisions and what data we used, no one could be like, Hey, this is your fault. Right. Right. Yeah. And so that's kind of how I approach that situation. but you have to really get through the fact that I think I used it.

35:20I probably, I probably stole this from somebody. It's called Q-tip, quit taking it personal. And that's the toughest thing. So once I quit taking it personally, I then started to be like, why, why are they behaving this way? There's got to be a reason why a reasonable person would behave this way. I only have one that I haven't been able to figure out. And I don't know whether, I don't know the person ended up getting let go at some point, But, and as you were talking about this archetype, I was thinking like maybe that was what they were, but, but this person took it a little bit further and maybe it's more narcissism.

35:55And I don't know what you think about, about this, but, but, you know, we would have similar conversations. We would say, okay, we discuss something. All right. Do you agree? Yes, I agree. I'd go in and present and do the conversation. And then the person would be like, it was almost like they'd never even heard of it before. Right. And they're like, what are you even talking about? And I'm like, we literally had this conversation yesterday. I walked you through. And I would be saying this in the meeting, like I walked you through it. And then this person would be like, we never had that conversation.

36:33And the fact that you think we did, is an issue. I'd be like, am I crazy? That's a reality distortion field. I'm pretty sure like we did. And it was, I think they were just, I don't know. I think they were a bit of a narcissist and maybe a bit crazy, but you know, it was why it sounds pathological. That's beyond just being a professional that's overloaded or fearful or insecure, that is pathological. Listen, I'm not a clinician, but that is challenging. Yeah, there's other stories that I won't tell, but yes, I mean, but so, I mean, and that's an extreme. Like most people are not like that. I think I just got very unlucky in that situation.

37:22But most people, to your point, if you get curious, there's a reason why and generally would you sum it up as fear i would say fear uh is a component i would say insecurity is probably the biggest one because we're talking about in the end of the at the end of the day we're talking about people's livelihoods here right so um i think uh there's a saying and it's usually expressed in crudel language but it takes uh what is it how's it go it takes one oh poop to destroy like 10 attaboys, right? There's probably a better way to say it, but it's true, right? And so their goal is to avoid any type of negative fallout, any type of victim, you know, fault, you know.

38:09And so it comes from having a fixed mindset. And so what's interesting is Carol Dweck wrote a book called Growth Mindset, maybe about 10, 15 years ago. I love this book. In fact, when I got it, I had an opportunity to spend time as part of a leadership group at Microsoft with Satya Nadella, who transformed the culture of Microsoft, because I'd grown up there during the Balmer and Gates days, night and day companies for the better when 2014 struck and Satya took over. So he sent a book. He says, everybody that's coming to the leadership conference needs to read this book. And the book was Growth Mindset.

38:42I'm like, I'm Eric Sharron. Of course I have a growth mindset. And their admins reached out. They're like, if you're going to attend this session, then you need to make sure you read this book because he's going to ask. I'm like, oh, rats. Okay. So I should read this book. First 20 pages changed my life. It became less about fearing failure and trying to make your failure sound like successes and more openly admitting your failures and saying, here's what I learned. And this is what I'm going to do better next time. It's less about being perceived smart and flawless and more about learning it all and being a grower and thinking about how you can take what you failed at and then make it successful and deliver results.

39:20So typically when I encounter people that are having this fear or insecurity, it's because they are in a fixed mindset mode. And that's not a fault for anybody, but the goal is to kind of manage upwards and show your leader that you can actually extol failures. You can have a slide that says what went well, what went wrong, and what did we learn? Like that's the whole, you could actually be really open about it. Yeah, no, I love that. And I love that you're saying that. And that book was a good book. And I loved it too when I read it. And I think I want to get in because we're running out of time, which is really sad because I'm having so much fun.

39:53But I wanted to do a couple more things. First, I want to get into a little bit about some advice for employees and then some advice for leaders, because I think that that's really important. So if I'm an employee, whether I'm new in my career, but I think it's, you know, especially for newer folks, because you're just learning. But even if I'm in my career and I haven't, you know, I haven't done this, like what's your advice for me to navigate this? One, I should get your book. Yeah, yes, definitely. I was going to say that there's so many lessons. There's so many lessons that I learned over the 25 years I've been doing this.

40:30I would say first, don't try to not feel your feelings. process your feelings and your emotions. I am not a very emotional person. You can ask my wife or anyone that knows me, but that's because I've been through so many things that I'm like, oh, I've been here before. Nothing surprises me. Nothing shocks me. Me neither. Yeah. So knock on wood when you say that, but like you've seen, you've been around the block, right? Yes, I have. But for early career people, definitely process your feelings, but also remember that it's not personal. Many times it's not personal. Assume that it's not personal.

41:00Assume that this is just a bad set of behaviors that this person is using as tools and they don't know any better. Have that be your going in assumption and then develop your curiosity. Figure out what is the core motivating factor? What is it like to be this person? How difficult is it? And if you don't know and you can't imagine because you don't have that depth of experience, ask them. Say, it seems like this is what I'm noticing, but it seems like it must be tough on you for these reasons. Yeah, get curious. Get curious, absolutely. Once you've figured out that motivation, and maybe the frame for this book will give you a good set of archetypes in which you can be like, oh, I've seen these behaviors before.

41:39Because mid-career, you're going to see these behaviors repeat. These tools are systemic, right? And so the other thing I would say is try to grow your manager. Try to be of service. I often tell my new managers when I meet them, it's like, my job is to never surprise you and to make sure that you're fully aware of everything that we're doing and that you're fully supportive. So the goal would be to be of service to your manager. My job is to make your life easier and not surprise you. So how can I do that best? How can I help you? And people think about that, like, you know, that managing up aspect as like, you know, ass kissing and it's like, yeah, no, it's not that it's not that it's like, and it's not like you covering your own ass either.

42:21It's like, it's just communication. It really is. And it's managing up or better yet. I don't even think we should call it managing up. Managing expectations for anyone is important. It really is. You have to grow. Sometimes you have to grow your manager. I think a lot of early in career folks have this all, because I know I did, of your managers. These are people that are senior, more senior than you. they literally hold your economic welfare and your career prospects in their hands and the organization has imbued them with a sense of authority because they must have done a good job to get to this position and so there's this there's this yeah this is there's this halo effect that a new early in career person has with their managers before the bad behaviors start to manifest and then it's like well how can this person that's been kind of like has this halo So treat me this way.

43:16It must be me. I must not. So the other thing I would tell early in career people is know your worth. And I'll tell you this because we hire a ton of early in career people. I'm fortunate enough to be in talent reviews for these people. We value early in career people. We value people coming in from the outside that think differently or don't have biases or haven't been in this business for 20 years that are going to be the next groundbreaking people. And many organizations say they want that, but I actually do want that. because typically when you come into an organization, they're like, okay, don't be too different now because this is how we do things here.

43:49Yeah. A little bit, but not really. Yeah. Yeah. Just don't be too different to make me uncomfortable, which is really what you need. You need to make people uncomfortable. But so there's that confusing, but know your worth is the most important thing because you can try every bit of advice that I give in this book. But I think I write about in the second, the second half of the book, which is sometimes it may not work out and you have to know yourself enough to say it's time for me to find a new leader my father always told me never look for a job no no it goes look for a job when you're happy with the one you have because if you're running from a burning building you could run out of that building and run into a building that's more on fire than the one you have right because everything looks good when your house is on fire yeah right so smart guy it's so true very good advice when when it's burning down don't don't be running into the next burning building because you're desperate at that point.

44:38So, okay, now let's shift to leaders. What's your advice to leaders? My advice to leaders is to try to be self-aware and to challenge yourself. So like earlier in the context conversation we had is that they don't know what you know. You have to cascade the information that you're getting. And the context is probably like the oil or the glue that holds the team together. It makes things operate smoothly. People understand the stakes. They're not operating with an insufficient component of what their role is and what their job is and why it's important. And it also actually helps your team because they feel that you're investing in them.

45:15It makes them feel like you care about them and that you don't just think of them as cogs doing a job. And so cascading those things are super important, providing that context. Yeah, no. And the only thing I'd add on that is like, I think I got really good at knowing my limitations as a leader. And I would just say to people very openly, these are the things I'm really good at. I'm really good at this. I'm really good at that. I'm not great at this. I've tried to be, but I'm not ever going to be, I don't think. I keep trying though. So don't, you know, don't hate on me yet. I'm going to keep trying.

45:57You know, this is what you can expect. You can expect this from me. And here's what I expect from you. And also I want to hear from you, right? Like if I'm not doing well on this dimension or that dimension, or you need more or less from me, I want you to tell me. And I think when leaders can be very honest about what they're great at and what they're not great at, have that self-awareness, but then open in feedback and regularly ask for it. And because they're not just going to give it to you because again, of this halo effect and you're anointed, you're the, you know, whatever. I always tell people like when they're promoting, I'm like, congratulations.

46:40Now you, you know, now you have a crown. Um, just don't act like you do, you know, and, but it, I bet it's truly people then kind of from that day forward, see you differently and treat you differently. And they, because there's a lot at stake, they're not always going to tell you the truth. That's definitely true. As much as you can open up the door to the truth, I think it's the better. Sometimes also hearing the truth is difficult and challenging. And the goal for you is to not, to restrain becoming defensive, to restrain the fact that, hey, this person that's two organizational levels of seniority below me actually diagnosed something and delivered a recommendation.

47:21And I actually need to, you know, be self-aware, not react emotionally. And that's, that's tough for a lot of people. You know what I learned to do? And listen. Yeah. You know what I learned to do? Not to say anything, but thank you. Yeah, exactly. Just say, thank you. I'm going to go think about that. Right. Thank you. That's a great line. The other technique I use to actually have the other person walking away feeling heard, and this is upwards and downwards, like, you know, up and down the org chart, is use five words. What I hear you saying is. Yeah. So even if you don't agree, they will feel like they've been listened to because you now understand them.

48:02You didn't defend. You didn't contain. You didn't put it in a box, right? And so that works up and down the org chart. That's perfect. Okay. I forgot to tell you when we were talking before we started recording, we do these things called career confessions. It's where listeners send in questions and then we give them work advice. Will you do one with me? Yeah, sure. Sounds fun. And before we get into that, I always ask our guests to leave a little advice, a little something you want to give to the listeners. So before we get into career commissions, is there a nugget or something you want to leave us all with today to think about?

48:40Maybe two. Okay. Be bold, but don't be foolish. And then know your worth. Maybe those are the two best nuggets that I can give. I love both of them. I really have enjoyed this so much and I don't want to say, but we're in a career confession. I'm going to set up the question and then we can both give them some advice. Okay. I've spent years adjusting myself to leaders whose emotional chaos dictated my day. Sometimes I wonder how much of my career has been shaped by managing them instead of doing my actual work. So here's the question. How do I learn to actually lead my team instead of constantly having to manage my leader in places they aren't even aware?

49:22That is an amazing question because the more senior you become, the more it is about stakeholder. They call it stakeholder management. And really what it is is catering to the whims of people whose opinions actually matter because of where they sit in the org chart. Right. As callous as that sounds, that's the honest truth. If you want to take a negative look at it, I'm a positive person, but that's really what that's all about. So what I would say is if you're doing that in perpetuity, it means that you are managing the noise, but you're not getting to the root of the problem. At least that's the way I would look at it myself if I was thinking critically about the scenario you positioned.

49:58because I'm actually fighting the fires around the emotional volatility, but I'm not actually solving it. Now, sometimes you just get difficult people. Like the example you gave earlier, that sounded quite pathological, right? But assuming that that's not the case, and which might be my experience, that's not in the majority of cases. There are people there in which you basically have to say, well, I'm managing the volatility, but what's at the core of the volatility? How many different things cause this to happen? It's that curiosity that you need to look at this person with and say, what could it be like to sit behind their desk?

50:36What storms are coming or rolling downhill? How can I actually let this person know I'm there for you? Count on me. And how can I then say, even if you don't want to be. But again, it's like eating your vegetables or paying for insurance. it's going to pay off because it's going to make your life less chaotic because it causes you not to have to respond to reactions on stuff that's coming at them. So if you can actually figure out the motivation and the cause, and then work towards extinction of that behavior by helping them and growing them, then I think you're going to spend more time growing your own team and less reacting to the volatility.

51:12So it goes from building a thick skin, but still having the emotional eruptions kind of hit that thick skin to saying that you know what I had a thick skin and I value my thick skin but I'm actually going to work to prevent the eruptions from happening happening to begin with and I'm going to help you do it yeah no I love that you know I think oftentimes I don't think it's just in work I think it's in life but we often don't try to put ourselves in other people's shoes. That's right. And I, I'm a positive person too. And I think most people are good. There's like a few people that aren't good and whatever, but most people are good.

51:54And we're often more, we're not as far apart as we think we are. That's right. And when, and when you don't come at it from like, let me put myself in their shoes and try to of experience things from their perspective and also get curious about, about it. Um, and just, well, they should know, you know, they should just know that they shouldn't be this way and they should just know. Well, a lot of times they don't know. That word should is a very dangerous word when you're, when you're in these situations, figure out how many times, yeah, figure out how many times you say should, or you think should, and then say, well, that's not the way that it is, But this is a great observation because it's difficult to put yourself in somebody else's shoes when you're in the throes of experiencing that emotion.

52:42So you have to kind of work through the emotion. And then you just have to come to the realization while you're becoming curious, you're coming to the realization that most people are, in my opinion, most people are good. They just have bad tools and they don't know any better. And so once you understand the tools are bad. Exactly. they they're they're doing things how they were either figuring out or they've seen other people do it right exactly and that's why they don't know they don't know they're doing these things and that they're terrible and they don't know what to do that's right because nobody ever taught them exactly oh my gosh eric you have just made me so happy today i could talk to you for another hour about same same yeah yeah what's that isn't there a movie like bad bosses isn't it yes that It is a movie.

53:27Jason Bateman, I think, was in it. Yeah. Yeah. Great movie, by the way. Yeah. But I hope you come back. I'm happy to come back. Absolutely. If our listeners want to find out more about you and buy the book, I'm guessing they get the book anywhere books are sold. That's right. You can go to Amazon. You can search for, you know, Have You Ever Had a Boss That with my name, Eric Chiron. Definitely love to hear what folks think about it, good or bad. I'd love, you know, if you loved it, drop a note on Amazon, review it. If you didn't like it or you have different opinions, also drop a note on Amazon and let me know what you think about it.

54:03You can find me at author Eric Charon on TikTok and Instagram. But yeah, that's where I hang out most of these. Yay. Well, I am so grateful you came on the show. And I, you know, now we're friends forever. Yeah. Yeah. Thanks for having me. It's been great. You're welcome. Thanks for listening to TruthWorks.

From the publisher

We spend 90,000 hours of our lives at work—so why do we let one bad boss ruin it all?

In this episode of TruthWorks, I sit down with Eric Charran, Microsoft Chief Architect and author of the explosive new book Have You Ever Had a Boss That…? Eric isn't just a tech veteran; he’s a screenwriter and leadership expert who has mapped out the hidden "DNA" of dysfunctional workplaces.

We dig deep into the uncomfortable reality of modern leadership. Eric reveals the 9 Boss Archetypes that secretly govern your office (are you working for a "Firefighter" or an "Attack Sub"?), and we debate the difference between a "hard" culture and a "toxic" one.

As the former CHRO of Netflix, I thought I had seen it all—but Eric’s psychological breakdown of why bad bosses exist (and why we keep hiring them) completely shifted my perspective. If you feel stuck, undervalued, or burnt out, this conversation is the manual you didn't know you needed.

TOPICS DISCUSSED:

  • The "Attack Sub": How to spot the boss who sinks you from the shadows.
  • Netflix vs. Microsoft: Comparing the "Keeper Test" to Eric's "Dysfunctional Archetypes."
  • The "Firefighter" Trap: Why your boss creates crises just to save the day.
  • Managing Up: The exact scripts to use when your leader is the problem.
  • The AI Boss: Will algorithms eventually replace middle management?

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