The Bosshole® Chronicles
The Bosshole® Chronicles
Lilly's Story - A "Grade A" Bosshole
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The lights were bright, the stakes were high, and the work felt world‑shaping. Lilly stepped into national broadcast straight out of college, scaled a tiny shop into a multi‑crew operation, and answered calls when presidents landed or crises erupted—only to realize the culture fueling those wins ran on tests, temper, and control.
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Setting The Stage
John BroerWell, hello Sara. How are you?
Sara BestJohn, I'm real good. It's great to be together.
John BroerIt is, it is, and we have a bosshole story. I don't want to take any of the thunder away. Tell us a little bit about what we're gonna hear today.
Sara BestYeah, boy, it's been a while since we featured a Bosshole story. This one, um, it's it's some tough content for sure, but uh the takeaways are solid uh for for both managers and supervisors, and also people that may find themselves in a situation where there seem to be red flags. Bosshole red flags, and and even worse. So we're gonna hear from Lilly, who will share her story. And uh, what do you say? Let's dig in, John.
John BroerLet's do it. The Bosshole Chronicles are brought to you by Real Good Ventures, the talent optimization firm helping organizations diagnose their most critical people and execution issues with world-class analytics. Make sure to check out all the resources in the show notes and be sure to follow us and share your feedback. Enjoy today's episode.
Sara BestWell, Lilly, welcome to The Boss hole Chronicles. So good to have you today.
LillyThank you. Thank you for taking the time uh to be here. I appreciate the opportunity to share the story.
Sara BestYeah, it's a it's a good story, and we uh we appreciate you coming forward to say, I want to share this story. So let's start at the beginning. This is a boss hole story. So let's hear about what your experience was with your boss hole.
LillySo I was hired out of college two months after I graduated into a career path that became my career for the next 18 years of my life. And I stayed with this same company for the first 12 years of my career. I was young when I started and very impressionable. And I had the privilege of starting my career in those formidable years with a grade A boss hole.
Sara BestWow.
LillyAnd sadly, the writing was on the wall from the get-go, but I didn't know what to look for. I want to say I didn't know any better. I probably did know better, but here's the thing about this career is that my ego absolutely loved it. I was working in national broadcast television production at a production company that I wound up personally managing and growing from a team of three employees up to a team of 10 employees. We started with one camera package, grew to five camera packages. We bought a satellite truck so that we could do our own live broadcasts. We built a new building from the ground up to accommodate this growth. And I was proud of all of the growth that this company experienced under my leadership there. And I loved the work that we did. It was high profile. If the president of the United States was within a five-state radius of me, I would be the one that got the call to put the president's address on national television, providing the camera crews, the teleprompter, the satellite truck, everything to make the president look good. It was a lot of rewarding stuff and a lot of risky stuff too. I also had crews that spent 30 days straight in New Orleans covering the aftermath of Hurricane Katrina. Uh, if there were riots, our crews would go in and sometimes they would get tear gassed in the name of journalism, you know? So high risk, high reward industry. And there weren't a lot of opportunities in the Midwest to have that legacy be built.
Early Red Flags Surface
John BroerSo suffice it to say, fresh out of college, super excited about this amazing career. Maybe it was even more than you had anticipated, and it just kept on kept unfolding, which is really cool. When you were interviewing for this position, were you interviewing with that manager? Yes. Okay. What I wanted to find out is so you, this this ultimately the person that is the bosshole, you did interview with this person. Were there any hints of boss wholeness during the interview process? I I mean, looking back, you probably think there may have been, but was there any were there any red flags when you were interviewing?
LillyI think that a lot of the red flags that I ignored along the way were kind of his idea of testing people.
John BroerOkay.
LillySo the interview location changed at the very last minute from the office to his house that was two miles from the office.
John BroerOkay.
LillyNot a big change because it's nearby, but kind of a big change in the context of the interview setting. And that was then shared that it was a test of my flexibility, whether or not I could go with the flow. Because in our industry, you're going to be asked to go to this address to interview a random person and then sent someplace else to do. He was testing whether or not I had like, you know, the guts or the spa or whatever. So those were those tests that he would set up to test somebody's commitment to the career or their commitment to him was something that was a red flag on day one that I didn't realize was a red flag that wound up creating very toxic environments and relationships with employees throughout the years.
John BroerOkay. And I mean, hindsight's always 2020, as we know. But at the time, again, you're you're excited, enthusiastic, and you probably think, okay, no big deal, unflexible. We'll go ahead and have the interview here. And later you had some context. Okay, I just wanted to sense if there were any like really, I mean, during the interview itself, and I'm asking this for a reason because sometimes those boss hole characteristics are revealed so in such sharp contrast or in such clarity that people will say, Oh, this person must not be like this. I can I can overlook this. I I didn't know if there was anything that was super obvious. It just sounds like there were little hints. Does that make sense?
LillyOn day one, it was hints. Hints. I started, yes. On day one, there were hints. I started this career in September of 2004.
John BroerOkay.
LillyIn April of 2005, I got smacked across the head with a situation that I still to this day will never understand why I decided I was okay with ignoring it and moving forward.
John BroerOkay. So tell us about so tell us about that. You've been in the job for some time, and then you get smacked. Tell us about that.
The Vegas Line Crossed
LillySo we went to Las Vegas for an industry-related trip. And at one point during that trip to Las Vegas, he implied with these specific words, I think we could spend the night together. And I said, No, that is not going to happen. The next morning, over breakfast, he was very like sheepish with, it's really good that nobody ever finds out that I said that. It could be at risk to the jobs of all of your coworkers if my wife takes it the wrong way and decides to leave me and take half the company and all of that stuff. And I responded saying, as long as this never involves me, it's none of my business. You've learned your lesson that I'm not open to that type of an engagement with you and keep me out of it. And move forward from there for another 10 plus years, uh, you know, 11 plus years before an incident that was directed at me. Along the way, some of the things that I ignored were young women that would take in a position and leave within a matter of months. And then, of course, it was because I was a tough manager to work for, because what you know, the true story behind why they're coming and going was not something he could accept blame for. Uh, he had a temper uh and had an idea of how things should be done. And if people didn't fit with that, he'd be quick to snap. He'd thrown things at people in the field before from losing his temper. Uh, all of it seemed like, yeah, but at the end of the year, he's gonna win six Emmys for our company. And if you're on his team, then you win those Emmys too. Um also one of his MOs was, You did a great job today, but you only did it because I bailed you out. Here's where you would have failed if not for me. So recognition would always came with this stifling, but you still need me, kid, sort of an attitude. Yeah. Good job, ego.
John BroerGood job, but yeah, that's right. Can we back up real quick? So um this hint of just inappropriate suggestion of whatever you you shut that down right away. Yeah, but there was evidence potentially, or there was evidence that there were other women that were subject to this that perhaps didn't have the temerity to to shut it down.
LillyI'll never know for sure what their stories are, and I don't want to comment that. But that makes sense.
John BroerThat makes sense. Yeah.
LillyWhat I do know is that he he never seemed like he was hiding the fact that if he was out of town on a work assignment, he was gonna flirt with and and try to pick up whether it was a fellow producer that's you know, uh another crew member in the field, or somebody that he was interviewing that day and took a liking to. He was constantly pursuing women. And I think I assumed all along that his wife has to know and she has to be aware that he's this type of a person, and for whatever reason, she's okay with that. Um, and just I'm not, it's not my place to insert myself into that relationship. It's interesting because it is a husband and wife that own the company, and I'm aware of that from day one, but my allegiance was always to him, not so much to her. Right. And never feeling like if I've got wind that this guy is flirting around or sleeping around, it's not my place to tell her.
John BroerRight. Okay, okay. Good. Not good, but you know what I mean. Within a year, you experienced this at a conference at in an event, shut it down. Is the excitement still high? I mean, you're doing all this really cool stuff, and it is it enough to ho to sort of, you know, not ignore, but you know what I mean, sort of rationalize this unsavory behavior and just keep moving forward with the work? Or or when did it when did it peak and all of a sudden start to decline?
Awards, Temper, And Control
LillyYeah, so I spent years in a growth phase, okay. Growing the company, growing our team, growing the relationships with the freelance vendors in our area and the reputation of the business. I really enjoyed having not just national, but international clients that knew that they could rely on me to provide whatever they needed to get their event covered, their interview covered, their story told. Uh, we regularly won awards for the work that we did, and my ego was so excited for the next phase. Yeah, I built my career, my life around this career that I was building. My house that I bought was in, you know, less than a mile from the office. I was on call 24-7, and I felt important when my phone would ring after hours and I needed to drop everything to find out what Good Morning America needs for me today, to find out, you know, what is going on in the world and how we're going to be the ones to share it. Um, and it's also being that home base for the company was my full-time job, but I was also a freelance field producer right in the fold with all of this business. So they would call and say, We need a camera crew. I'd provide the camera crew through the company, and then they'd say, We also need a field producer, and I would go do that part of the assignment. So it's interesting because a lot of these situations are really risky situations, and you do get really close with the camera crews that you're working with. In some cases, you are trusting them with your life in these situations, and vice versa. If I'm looking this way while they're looking that way, we've got each other's backs. And you build relationships that be come to feel like family. And this man over the years became my like broken father figure in a way. And unaware that that's what was really happening in that setting, as you get closer to somebody in that situation, it becomes easier to accept their flaws and to overlook things. So, as my my personal ego for who I was and the career I was building, as that was growing, also my ability to kind of look the other way and accept him for his flaws also was happening at the same time.
John BroerOkay.
Sara BestWell, Lily, I gotta ask you a question, though. There had to be some impact, some cost to you for, you know, enduring that. Uh, ego aside, I mean, I totally get it. Like, ooh, this is amazing. I'm important, I, you know, they need me, I do really good work. I love that. And at the same time, this is not going well over here. What was the, you know, tell us about the impact on you during those years?
LillyWell, the overarching impact on me was having an ability to build close relationships quickly for all of in all of the wrong ways for all of the wrong reasons. All of the skills that made me a really wonderful field producer where I could meet somebody and instantly they trust me and they're comfortable sharing their life story with me so I can put them on national television, were the same types of skills that I had learned from watching and learning how he would endear people to him. And in just it's hard to break down the specific psychology of these tactics, but I inherently gained really nasty personal relationship skills, not just from the relationship with that boss, but the role I played in this industry.
Sara BestSo is that, Lily, is that the industry or is that this particular culture that this guy created?
LillyThat I think is the industry. To get good at that level in that industry, you want those traits. I think there's a reason why there's not a lot of um women that are also building families in that career. There's a lot of women in that career, but I did not see a lot of women that were also building families. And it's because of the sacrifice, not just of time, but I think of character too, in some ways. Sure.
Sara BestWow. That's thank you for revealing that and helping us know you in that way. That's incredible.
Ego, Family Culture, And Blind Spots
LillySo I'll tell you kind of when this all culminated and came to an end. Yeah, is when, you know, I am in my 30s at this point and am starting to think bigger picture about having a long-term relationship and what I really want to do with my life. And the man who at the time was just my boyfriend, but is now today my husband has said things to me along the way, like, this guy that you're working for treats you more like an indentured servant than a human being sometimes. He sees all of the red flags that I'm ignoring. And he decides that he is going to move to another state and tells me up front, I'm welcome to join him anytime I want to when I'm ready to kind of move away from this chaos, but he doesn't expect me to. And after he moves, I get to live in this area, this headspace, having my house to myself and really evaluating what life is like on my own in this career. And I start looking for other jobs. I start looking for other opportunities on the side. I'm contemplating moving for love, which seems silly to me. It seems irresponsible to my career-oriented mindset. Um, but I'm contemplating it every day of my life at that point. Do I move to another state because of the man that I love just moved there? Or do I just need to stay here and find something new here? All these things. And I think I can trust this bosshole of mine. I think whole in my whole being, I can trust this man with my life. I'm gonna schedule a meeting to talk to him about all of these things and talk through where I'm really at right now. We go out for dinner. I explain to him my situation over dinner, and we talk a little bit about it. And he gets drunk during that dinner and asks me to give him a ride home. And as I when I am in the in the car with him, dropping him off is when things get out of uh out of hand, things go a different direction. And he is explained to me over dinner, I'm not willing to lose you. If you want a raise, we'll get you a raise, but I'm not willing to lose you. And he had phrased it that way many times. And when I'm dropping him off, he reiterates look, I'm not willing to lose you. If you want to raise, we'll get you a raise. Tell me whatever money you want, because I just want to be with you. And the next thing I know, he is trying to make out with me.
John BroerOh gosh. Oh.
The Breaking Point Conversation
LillyIt had been almost 12 years since the last time I had told him I'm not interested in this type of an advancement. As long as it doesn't involve me, it's none of my business, but now it is my business. And in that moment, I am very rattled by the fact that this is a person I can trust with my life, but I can't trust them with my body. This is a person who I can trust with my life, but it turns out I shouldn't have trusted them with my brain because those early 20s, late 20s are really formidable years of your mental health, your psychological development. And it's like it all hit me like a freight train all at once. I had been learning bad habits from the person that I had put on a pedestal and looked up to as my father figure, my role model, my mentor in life. So my ego then is starting to crumble a bit at that point in time, and I'm angry and I have options. Do I burn the building to the ground? No, that doesn't seem sane.
John BroerBut attempting, yeah.
LillyAttempting.
John BroerYeah.
LillyRight? Do I call every single one of our clients and tell them how big of a monster he is and they should never hire this person or trust this person again? No, because I've once I've built a team of 10 people that rely on this business for a career. It's the only career I've had. I want to leave behind a legacy and a strong reputation, and all of that is now hinging on my ability to come to terms with this. And that's where personal accountability comes into play. Instead of taking that one moment where things didn't go the way I expected them to and playing the victim in that situation, I had to take into consideration the accumulative moments that I had chose to make a decision in those moments. All the times I didn't tell his wife when I knew he had cheated on her. All of those times that a young woman came and went from the company quickly, and I never bothered to find the real reason why. All of the times that he had built somebody up just to tear them down to keep them under his thumb. And I went, it's just the cost of doing business.
John BroerGoing back to your team. Well, first of all, Lily, thank you for sharing this. Cause this is, I mean, I'm sure at the time this was uh like you know, like getting hit by a truck. I mean, it's like you you knew the person was flawed, you had that experience, but all of a sudden your world is completely rocked, your foundation is rocked. I'm thinking about your other team members. You know, you built you built this team. Clearly, they're not, I don't know, I don't want to say ignorant or blind to their own exposure to this individual. Were there rumblings, were there conversations about Lily, you know, I'm experiencing this with this person, or what do you think about this? Or were they just sort of swept up in the excitement of the work too?
LillySo we would have weekly team meetings with the whole team, with the owner of the company. And we joked all the time that he was the whirlwind because he's gonna come in on that Monday meeting and stir things up and then leave us in the chaos of that hurricane that he just created. And the conversations that we had had, it was like we were all in this together. We were comrades in, and it's it was like the shared common enemy. And people had said things like, Well, the enemy you know is greater than the, you know, is better than the unknown. And um, there were a lot of jokes that were made. We we would joke to get through it. Um, and the industry as a whole is rife with inappropriateness. Okay. Let me just say that it's not uncommon to make a joke that you know is inappropriate just because it's gonna break the ice. You're in an industry with that regular degree of like sexual tension, sexual connotations, all of it, and you learn to blend in by making the joke yourself. It's almost hypocritical for me to look back and think, oh, I never made an inappropriate joke. It was, you know what I mean? Yeah.
Choosing Integrity Over Fallout
Sara BestYeah. So it sounds like Lily, when when you described your coming to awareness moment, like where the the truck crashed, as you said, or the train crashed, and you you realize all these things like almost at the same time, like who he was, who he was going to continue to be, who you had become, certainly uh both a product of the environment he created, but also the industry you work in. What I heard in there is you taking like your 100% responsibility, your like what in here is mine to own? Not not all of it, but what here is mine to own? Like, where did I get caught up in the the revelry of being needed and wanted and being at the front and center of all these cool things? What advice do you have for our listeners who who may some of them be coming to the awareness of, I don't want to be that guy? What if I'm that guy? And for people who might be saying, Oh man, have I been part of the problem? Is am I her? What advice would you have for them?
LillyYeah. So regardless of which side of the coin you're on, if you're complicit in a culture that is being developed in a negative way, which is what happened, the whole company had a culture of uh, you know, basically um accepting this, right? And so yeah, being complicit in in negative culture building, this is where dialectics to me comes into play. And not a lot of people are familiar with this term of dialectics, and so I'll explain it. Dialectics is the principle that in every given situation, more than one conflicting truth exists. Yep. So the age-old example is there's you know, you're looking at the coin and I see heads, and because I've got heads on my side, you see tails on your side. And it's easy to understand that when it's a coin and it's just two perspectives. But every situation in life has more than one conflicting truth. So when you've got a team of 10 people, and I'm taking into consideration that team of 10 people, that's at least 10 different truths there. They all have their side of the story as well. So my advice to somebody who is feeling maybe am I creating a negative culture at my company? Am I being complicit in a negative culture in my company? When I discovered dialectics and looking for solutions, it changed my perspective about all of the people and the role that they had played along the way here. Uh, it was a series of relationships that had been collected and built. And it takes time to build something and it takes time to unbuild something. And dialectical behavior therapy is something that is used rooted in mindfulness to help people to make better decisions and how they build their relationships. Essentially, in every given moment, there's situation A happens, our brain takes a moment to respond and comes up with response C. B is our brain taking the time to respond. When you make a conclusion enough times, your brain cuts out B and you start to go, A happened. It makes a shortcut for us because that's what it's neurological processing job is to do. And C happens without us even realizing it. Practicing dialectics, whether it's in the moment along the way, as you're building something, or more importantly, when you're working to unbuild something, that's you're getting your B back. It's getting back that ability to stop and process what all of the possibilities are right now.
Sara BestYeah. This sounds a lot like cognitive behavioral therapy, where we have an activating event, B, that's the A, it's out of our control. The B is the belief, the thoughts we have about it, the spin we put on it, C is the resultant emotion and behavior. And you're talking about working with the B, making sure the B is front and center. Um, can you give our listeners a practical example of like maybe something you encountered where the A, B, and C you worked with those and came up with something different?
Dialectics And Reclaiming Agency
LillySo here is a prime example of A, B, and C. Okay. Yeah. Um, even just going back to how do I handle the fallout of this situation? Obviously, I'm not gonna stay working here anymore. My integrity has been compromised too much to move forward with that. Um, evaluating those options and what I'm going to do was very much focused on B. If I were to take a knee-jerk reaction and say, A happened, A is, you know, this cut and dry sexual harassment. You want money, I want to be with you. Let's make that happen. Can't move forward in that relationship anymore. So the relationship has to end. B is how do we handle the ending of that relationship? Because I think that if it was most people would leave with anger, they would seek consequences, they probably would not have done what I did in the B moment there. My B moment was choosing to preserve the integrity of the business that I had built and prioritizing that and working with the team to put together a situation where I could train a replacement instead of leaving them in a lurch to struggle to ensure that the employees, the team members that I had relationships with there and valued those relationships weren't negatively impacted by this one bad incident in this relationship. They know who he is just as well as I do. If they want to keep working for him, that's their truth. I don't want to be the one that shatters their pursuit of their truth.
John BroerThat's a really interesting perspective. Something else, when you talked about the meetings and sort of sort of the tolerance and nervous laughter and things like that about jokes and all this other stuff, that sounds like Stockholm syndrome. You know, it just sounds like, you know, and I know it's it's creating a sympathy for your captors and uh the people that are controlling. But I mean, I I actually think that there's something to that. It's like, hey, we're in this together, we're a team, we we love and respect one another, and there's this crazy person, but we're gonna be okay. And that's not healthy either.
LillyNo.
John BroerYeah. So here's my question. What happened? Okay, so you leave. No, yeah, finish your thought. Go ahead. Have your thoughts. I don't want to go ahead.
LillyThat's okay. Yeah, no, it it one of the jokes that we did make at one point in time that sticks with me now is and I don't think it was me that said it, but I would I don't remember for sure who it was. Boy, aren't we all lucky that he decided to go into broadcasting instead of starting a cult. Because this guy would have been a wonderful cult leader.
John BroerWow. Wow. So what happened to the team? All right. You leave, you tried to make a uh you tried to be above the line making the exit. What happened to the team?
Practical A‑B‑C In Action
LillyI was the only female on the team at that point. And all of the guys stayed. There were a couple of them that told me it was hard to stay. One of them told me this is something I'm gonna struggle with for my entire life, but I do have a wife and kid that are counting on me for this income.
John BroerYep.
LillyAnd I, you know, and so then there it is. Um, those same, some of those same team members that made the decision to stay in that environment when I was leaving it are probably being tear gassed covering riots in the street alongside this person right now. And it's their passion, it's their pursuit of their happiness.
John BroerYeah.
LillyAnd my experience is not their experience. And as much as I think we want to encourage people to change for the better along the way, all right. I I am a coach and consultant, and my role in life now is helping people to pursue continuous improvement. I want to support people to grow and change along the way in their lives, but I cannot make that decision for them. And when those team members decided to stay there, that was their decision. What I can do is support making that decision as prosperous for them as I could.
John BroerGood. And that's not an easy thing to do, but you knew what was right for you. The only reason I ask is that we've had so many boss hole stories where somebody leaves and you know, within a matter of months, matter of you know, maybe a year or two, the team just completely collapses or the the boss hole moves on. Thanks for letting letting me know. Um, I mean, I think it's disgusting that being the only female there, that this had to fall to you. Yeah. Go ahead, sir.
Sara BestWell, so Lily, as we kind of wrap up our session here, one question I have for you is you know, knowing where you are now, totally different career, what is your greatest gift out of this experience? You know, I know you shared you learned about yourself and your ego, all the things. What is the greatest gift of this challenge that was presented to you?
LillyFirst and foremost, the greatest gift that I have is I am now happily married to a man that was so committed to preserving my integrity that he was willing to physically move and create a new life for us. Okay, so that is the guy. That is the guy. That's the guy. Yeah, that is he's my dude. He's a keeper. He's a keeper. Okay.
John BroerYeah.
LillyKeeper, we've got a wonderful family, and clearly that is the greatest gift. But between the marriage and starting the family is a really quirky gift that I think I never saw coming, and I don't think anybody would see it coming. And it's improv. In my immediate pursuit to find that personal accountability and accept that it's on me to build healthy relationships in my life. And what tools do I need in my toolbox to be better at, you know, acting on red flags instead of ignoring them and building healthy relationships in my environment. I discovered that dialectical behavior therapy leaned hard into dialectics and also started taking improv classes.
John BroerWow.
Team Dynamics And Tolerance
LillyAnd what I found is that they really support each other. This idea of acceptance, it's yes and whatever your truth is that you're presenting, I'm gonna accept that as your truth and I'm gonna add to it and build to it with what I think this character should have and what I think this character should be adding. So that that moment to stop and assess what is the character I want to be portraying. And in improv, it's quite literally a character. Am I gonna have an you know an accent? What's my physicality? But in life, it's our personal character, the human being behind everything else that we're doing with morals and values and ethics, and defining that character in the face of our environments and the decisions that people make that are out of our control, recognizing we can always choose our character first and control what's within our control.
Sara BestYeah. Boy, I like that choose word in there, knowing that uh it sounds like I'm I'm not good at improv or anything like that. But what I get in there is there's always a moment of choice, and and the choice is endless. And what your story helps us understand, Lily, is as the reality became clear for you, you could have been an incredible victim. You talked about feeling like a victim, but you changed your be. You you told a different story to yourself, you chose a different way to exit and to actually even experience the whole thing, which is available to all of us, and and even in the small situations, not the ones as you know, um serious and awful as what you encountered, but each and every moment, how we have this ability to go, yes, and this and this, like whatever we say to our brain, the brain doesn't know the difference. It it responds in kind. So why would we not move in a direction that's um life-giving and clarifying and empowering? Yeah, good stuff. Wow.
John BroerYes, and thank you for sharing this with the bosshole transformation nation. This is great. This is great. Yeah, and and that that is that is not an easy thing to relive, but again, it these these experiences define uh and hopefully shape who we are. And clearly, Lily, you've provided some great context and great perspective. So thank you.
Sara BestThank you. And friends, we'll see you next time on the Bosshole Chronicles. Stay well.
John BroerThanks very much for checking out this episode of the Bosshole Chronicles. It was so good to have you here. And if you have your own bosshole story that you want to share with the Bosshole Transformation Nation, just reach out. You can email us at mystory at the Bosshole Chronicles.com. Again, my story at the Bosshole Chronicles.com. We'll see you next time.