Episode 02 - Toxic Leadership Explained: What Makes a Bad Boss with Mita Mallick
This week on The Lift, Ben is joined by Mita Mallick, leadership strategist and the author of The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses (and also a self-proclaimed former bad boss).
Key takeaways:
Bad bosses are created, not born: Toxic leadership behaviors often emerge under stress, pressure, and unexamined power rather than from personality alone
Managers have an outsized impact on employee mental health, influencing wellbeing more than doctors or therapists and nearly as much as a spouse or partner
Poor management training fuels toxic leadership: many first-time managers are promoted for performance, not people-leadership skills, leading to micromanagement and fear-based control
Developing confidence and identity outside of work helps protect employees dealing with a toxic boss, by reducing burnout and restoring agency when leaving isn’t immediately possible
Self-awareness and vulnerability are critical leadership skills
Feedback, reflection, and accountability are essential to becoming a better boss
According to this week’s guest, Mita Mallick, bad bosses aren’t born, they’re made. Mita brings a rare combination to the conversation: she’s lived the worst of it. She’s studied the patterns, and she’s also willing to say out loud what most leaders won’t – that she, herself, has been a bad boss
One of the most haunting examples from her career is about a boss she nicknamed “Medusa,” known for screaming, public humiliation, and unpredictable tantrums. Her point in sharing isn’t shock value; it’s the reality that this behavior often gets normalized as “just how they are,” especially when fear-driven leadership produces short-term results.
But Mita makes the business case that too many companies avoid: when a boss behaves badly, teams lose clarity and momentum. People stop taking smart risks, communication gets distorted, and, eventually, performance suffers. Toxic leadership doesn’t just hurt feelings; it breaks productivity and execution.
One of the most jaw-dropping moments in the conversation is the mental-health data Mita references. Research from UKG’s Workforce Institute showed that managers impact employees’ mental health (69%) more than doctors (51%) or therapists (41%), and about the same as a spouse/partner (69%).
That statistic reframes “bad boss behavior” as more than an HR issue. It’s a leadership and wellbeing issue with real consequences, and it explains why so many people DM Mita long, painful stories asking how to survive a toxic manager.
Then layer on a structural problem: Many organizations promote high performers into management without teaching them how to lead. “Congratulations, here’s a title and a team of 10. Now figure it out.” That “doing → directing” transition is where micromanagement, perfectionism, and fear-based leadership often begin.
Ben asks the question everyone wonders: If bad bosses are the worst kept secret in a company, why are they still there?
Mita is blunt: It’s often not HR’s call. HR may document patterns and advise accountability, but the decision to protect a high-performing toxic leader frequently sits with the CEO or business leadership, who can justify it with numbers, relationships, history, or convenience. The message to the organization becomes results at any cost, favoritism wins, and (thus) the culture is negotiable.
But in today’s workplace, where employees can post, rate, leak, and speak, senior bad-boss behavior is increasingly public and reputationally expensive.
This episode isn’t just for people enduring a nightmare manager; it’s also a mirror for leaders. Mita offers a practical self-check:
Trust your internal moment of knowing. If you ended a Zoom and felt that post-meeting wince because you snapped at, dismissed or got sharp with someone, sit in the silence and name it. Repair starts with admitting it.
Look for the signals you’re ignoring. People go quiet around you. You’re the last to know what’s happening. Exit interviews (when done well) leave breadcrumbs.
Ask for feedback with structure, not vagueness. Instead of “What should I work on?” (which can feel unsafe in a power dynamic), try: “Here’s what I’m working on, can you tell me what you’ve noticed?”
When it comes to escaping a bad boss, Mita knows not everyone has the privilege to resign on the spot. So she recommends a survival strategy that protects your future:
Keep your resume ready (always).
Start networking before you’re desperate.
Identify internal transfer options when possible.
Decide your expiration date (“I can do this for another 6 to 12 months.”)
Rebuild confidence outside of work – volunteer, coach, return to a hobby, create something. Toxic bosses shrink your sense of self; your life outside work needs to expand it again.
Poignantly, Mita shares how grief after losing her father intensified her “bad boss” tendencies and how vulnerability (not oversharing) can create context that reduces misinterpretation and increases humanity. The goal is not to excuse damage, it’s to stop repeating it.
If you’ve ever wondered how bad bosses get made – or worried you might be on the path to becoming one – this conversation gives you language, tools and a framework to lead with more clarity, courage and care.
Links:
Full Transcript
Read the full transcript
Mita: When the boss is behaving badly, no matter what the behavior is, you're not clear on the business goal. You're not able to drive results. I think that's what individuals should be really concerned about, because for too long we've let bad bosses hide in plain sight.
Ben: Welcome to The Lift, the show about leadership, growth, and getting what we want. I'm your host, Ben Brooks. For over a decade I've worked with CEOs, their executive teams, HR departments, and entrepreneurs to identify what drives their success and what holds them back. And now I'm excited to share those insights with you. On The Lift we pull up to see the bigger picture from accomplished leaders who know how to get things done in a rapidly changing world. We've got all of that and a lot more coming up next on The Lift. Hey everyone. Today we're talking bad bosses. Like exes, we've all had one. Today we're joined by Mita Mallick, the author of The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses. In the episode today Mita and I chat about the conditions that make a bad boss and how we can catch ourselves potentially becoming one. This conversation went in a direction that I didn't expect and actually made me feel a little empathy for bad bosses. So let's get into it. Well, Mita, welcome to The Lift. At the beginning of every interview, we like to start off with a few rapid fire questions to lift us up. So are you into cats or dogs?
Mita: Neither. Neither.
Ben: Okay. Fair. Favorite sandwich?
Mita: Egg salad.
Ben: What was your first job ever where you were paid for time or effort?
Mita: I was an assistant wedding photographer and really sucked at it.
Ben: Whoa. That's intense.
Mita: Yeah.
Ben: How would you describe your leadership style?
Mita: Being in service of others. That's what I aspire to do.
Ben: If one of your best friends described you in a few words, what might they say?
Mita: I hope they would say hilarious and loyal.
Ben: And how would your last boss describe you?
Mita: Curious, committed, courageous.
Ben: Well, Mita, bad bosses — something, you know, people have made movies about, and there's a lot of jokes about, and a lot of nightmares about. Can you tell us about some of your worst boss experiences yourself as a place to start?
Mita: I wrote a whole book about it, so I'm not sure where to start — The Devil Emails at Midnight. But let me tell you, one of the most painful ones, right, to still talk about, or the ones that I included, to actually write and sit down and think about, and that was my boss, who I nicknamed Medusa. There had never been anyone at this point in my life — not my parents, not my brother, not my husband, certainly not my friends — who had screamed and yelled at me the way she did. Screaming, yelling, publicly, privately, humiliating, berating — Ben, she was an equal opportunity bully. She went after everyone. She had temper tantrums like a toddler. I didn't have children at this time yet, so now I go back, I'm like, yep, that's what a toddler would do. Throw pens — and also threw a Chanel shoe at a colleague. True story. And to me, to this day, I don't understand why we allow this behavior to exist in the workplace. I understand, on one sense, because fear drives short-term results. I showed up to work every day scared. I thought I could outwork the bully. I thought that if I just worked really hard and did really well, she would leave me alone. It didn't matter though. And then what ends up happening is you get tired of being scared every day. It's like, I live in New Jersey, and when you get the notice that the black bear is roaming around the neighborhood and it shows up in your backyard and you have that visceral reaction — imagine every day that feeling. You just — the adrenaline just doesn't keep going. Your body starts to shut down. You start to go under the radar. You start to just not care anymore and think, it doesn't matter what I do. And I like to talk about the analogy of the candle — the light starts flickering out.
Ben: You know, when I was, you know, preparing for this and learning about your book and your research and the reason for you writing this, you know, it was interesting 'cause when I was in college, I had a leadership studies program I was a part of. One of the overarching questions we asked for four years was, are leaders born or made? We never — and this really hit me when I was looking at your work — the idea of bad leaders or bad bosses, born or made. It was always about good leaders being born or made. And I'm just thinking about Medusa and the impact on you, but just this person was probably not born as a little kid this way — or maybe they were. But, you know, how did you start to explore how people become bad bosses? Because I think everyone likes to talk about their toxic work stories or these other things, but you're really looking at some of the genesis and how these get shaped and created. What had you even start to explore this question?
Mita: So the genesis of the book started with my mother's home being flooded and destroyed pretty much a few years ago. She's now back in the home. It's been rebuilt, but I was with her when we were going through things in the house. Anyone who's been in a home that's been affected by fire and water — it's very traumatic. So imagine, Ben — I'm in my soaked childhood bedroom. I find report cards from elementary school. I was the proud editor in chief of my fifth grade newspaper. I see it. All these things we hold onto. And I found a notebook in my twenties — it's a notebook from my twenties — and I have a list of bad bosses. I had nicknamed them, all these things they had said and done to me, and it was quite detailed. And as I was driving away from my mom's soaked home and we're trying to recover things, I had this moment where I thought, do you remember Mean Girls and the Burn Book? And I thought, well, what if I'm in someone's notebook? What if I have done this to somebody — whether it was, I hope not, being a Medusa, an exacerbated bad boss situation — but I think we all have bad boss behavior tendencies, and they show up during moments of stress in our lives, both professionally and personally. And I've been the person that's contributed to the literature in the marketplace on how to survive a toxic workplace. The number one DM I get is how to survive a bad boss. They're very long, painful stories strangers will send me. I just think to myself, why aren't we having the other conversation? Why do we allow these people to continue to do hurt and harm — and oh, by the way, some of these people are us.
Ben: What have you noticed? Is there any theme or trend or thread across bad bosses, or traits around a variety, the personas that you've mapped out?
Mita: I think it goes back to the question you just asked, like, how are they made? And it's in these moments of stress, and I hate to say hurt people hurt people — it's an overused quote, but it's true. Hurt bosses hurt their teams. And so whether it's, number one, something's happening in the marketplace — like, oh, by the way, we're in the US, lots of conversations on tariffs, what's happening with the economy — it's causing a lot of stress for businesses, it's causing a lot of stress for individuals. Bad boss behaviors. Second, in my house we say, poo poo trickles down. So you're working for a bad boss. You're working for me, Ben — sorry. Early in my career I was Micromanaging Mita or Maleficent — I'm not sure what my team nicknamed me — but you might absorb some of my behaviors, 'cause it's your first time leading and I'm your only example. And then number three, something devastating happens in your personal life. It's an earthquake. You lose someone you love, miscarriage, you're struggling with fertility, divorce, breakup, move, you're sick, someone else is sick — I mean, I can go on and on. And in the interconnected world we live in, you could have family across the world and something's happening to them that's affecting you. And then that's when you have stress and bad boss behavior occurs, because guess what? When I can't control things in my personal life, I can certainly show up to work and control my team. That feels good, doesn't it?
Ben: And as a boss, you're in a position of legitimate authority to be in control, whereas in the rest of your life, if you're just a part of the family, you're not necessarily anointed — unless it's a, maybe, matriarchal or patriarchal side, depending on how that structure — but at work, you are legitimately in charge of something if you're in a supervision role, and you can abuse that power.
Mita: Listen, I like to say I'm in service of my team. I try to approach my work that way. But at the end of the day, titles still matter. There are still power dynamics in our organizations, and our bosses can make or break our experiences. And there was a recent study — I put a nod to it in the book, but not the actual study, it hadn't come out yet — and the study said that two thirds of people say that their boss has the most impact on their mental health. Two thirds. And you hear that and you're like, yeah, I'm part of the two thirds. That's me. Raise my hand. But not your partner. Not your best friend. Not your parents. Not your children. Your neighbor, your roommate, your clergy person. Right. It's your boss.
Ben: You know, I had a friend a long time ago talked about managers are gem cutters at their best, right? They're shaping this precious thing. I also think, you know, people can get quite ground down. And when you thought about, you know, maybe are you in someone else's book or burn book or notebook — you know, early-twenties Mita, that might have been, let's say, hands-on would be the positive phrase of micromanaging. What was going on outside of work that maybe impacted how you were showing up in your position of authority and control at work?
Mita: That's a great question. I think I was newly married, had a big job, was living in Manhattan. All the things — just lots of stress. Like, oh my God, the rent is like this much, and then we're moving here, we're doing this. All of those sort of things. But in that situation, I do think so many of us are put into leadership roles, and we've never been given any sort of training or support. And so it's like, hey, Mita, congratulations. You're doing so well. You are gonna get this title, you're gonna get this office, and now you get to be in charge of 10 people. Yay. And you're like, what? I don't wanna be in charge of these 10 people — but also, how do I do it? And so I find that what we talk a lot about in terms of micromanagement really shows up — that first bad boss behavior — is when you go from doing to directing. And that was certainly for me, 'cause no one told me that I'm not supposed to do Ben's job for him. I'm supposed to teach him how to do his job, and oh, by the way, I need to step in to what I'm meant to do, which is to oversee this team of 10 people. But we don't often have those conversations when we promote people, but especially for the first time. It's like, here you go. Congrats.
Ben: And I think people that are ambitious earlier in career, part of the pattern recognition is people want to be a manager, even if they don't wanna manage people. Because a manager means often you make more money, you get invited to certain meetings, or you have certain perks, or you're looked at a certain way, or you are, you know, offered equity or bonus or these things that you might not. So we've set up a game in the work world through hierarchy and rank and authority that that's an aspirational thing, but people sort of want the upside, the accoutrements of that. But then there's the daily caretaking and direction and, you know, challenge of dealing with and managing people in a team, which I do think some people resent and have a bit of a sort of a management hangover when they get that first job. And some people don't wanna do it. And you're to —
Mita: Exactly. To your point, this is how our workplaces were constructed. It actually goes back to manufacturing days. You think about, we're on a line making widgets. You and I are doing really well, but for the last week I've outpaced my KPIs. So the head of the plant comes to me and says, you're doing so well at this, now you get to now oversee what Ben does and these other five people. Just because I have individual expertise doesn't mean I can now lead people and teach them my expertise. And yet too often we have forced people to lead other people. And I think a lot of what I'm seeing in tech is really inspiring, particularly when you think of the engineering track — you can actually continue to make more money, be recognized, continue to get deeper and deeper expertise, and guess what? You don't have to manage anybody. It's an individual contributor track. And so I think you'll see that happening more and more, because a lot of people just say, I don't actually want to lead other people, and I don't know how to do it. If you're not gonna teach me how to do it and support me, I'd rather just stay doing work alone.
Ben: A lot of people don't want to do both roles — both the kind of technical, so whether you're a product manager or a sales person or an HR person, the content of it, and the people supervision. But again, we've incentivized getting into this sort of bundled role. So for organizations, if they wanted to learn from how engineering or tech is doing some of this, what are they doing to kind of help separate those out and to celebrate people that are sort of that thought leader rather than the people leader?
Mita: I think it goes back to something you said earlier, which is that, why do we want to get the manager title? Like, why do we feel forced into it? It's about feeling recognized and valued. You said something really interesting. Yes. You get invited to the meetings. It's not just about the compensation. So to make people understand that just because Mita is an individual contributor and now has deep expertise and a thought leader in the company doesn't mean she's being sidelined or sidetracked. She's still invited to the meeting. She's still part of leadership. This is how it's looking different for her. You have to role model those things, because then you have to make it attractive so that other people might wanna do that. Then there has to be a balance. I mean, somebody has to be leading in our organizations. Right. But there's a balance between people who are gonna do individual contributor work and lead teams. And guess what? As you know, careers ebb and flow. So I might wanna do individual contributor track for a while and then, like, actually now I'm interested in leading people, or vice versa. And we can go back and forth.
Ben: I do think that you mentioned something very important around, you know, context stressors at work or beyond. And I keep actually Russian nesting dolls on my desk — I got this in Abu Dhabi — and I remind people, right, that things resonate, right? Good behaviors from bosses duplicate out. There's a ripple effect, but also, yes, bad ones. And thinking about a bad manager at the frontline supervision level, right, is one thing. But when you think about a bad manager maybe higher up the hierarchy, where maybe multiple chains of management or up the hierarchy — what happens when we have a bad boss in a more senior executive role?
Mita: I go immediately to how is it impacting the business and revenue and the bottom line. That's what's happening. Because a bad boss can be behaving badly in all the ways that we talked about. Fear long-term will kill your culture. It will kill creativity, innovation, collaboration, all those things. But when the boss is behaving badly, no matter what the behavior is, you're not clear on the business goal. You're not able to drive results. I think that's what individuals should be really concerned about, because for too long we've let bad bosses hide in plain sight. And I think those days are coming to a close, particularly as you look at some of the recent bad boss behaviors in the marketplace, and whether it's a range of stakeholders — shareholders, the board, customers, right? We all have a microphone over the last two decades. Social media has changed the world forever, and I can now go on LinkedIn and Glassdoor or talk to the media and talk to people about what's happening in my company in terms of bad boss behavior. The more senior you are, the more public you are, so your behavior is on display for all. Versus, I might be a new manager micromanaging, you know, the bleep out of you in the office behind closed doors and just redoing everything you do — but that might not be as much on public display.
Ben: How did it come to be that HR tolerated or allowed — 'cause HR is not blind to some of these people being bad bosses. And so what's going on organizationally that they're remaining? Because it's often not a secret internally, and increasingly externally.
Mita: So there are many theories, right? One might say HR individuals might not be skilled in the work of investigating, holding leaders accountable, particularly if you've always been taught to really just focus on controlling costs. I would actually argue there are a lot of HR professionals who are quietly doing the right thing behind the scenes. And what most people don't realize — it is not the CHRO, ultimately, who decides — the Chief Human Resources Officer, Chief People Officer — if Mita stays or goes. It's Ben — and I'm gonna put Ben in the bad light here. Ben is the CEO who decides to continue to overlook Mita's bad behavior. They come with a list of things that Mita keeps doing — like, they've got evidence — and Ben's like, oh, but he delivers such great numbers, or he's got the customer relationships, or he knows the code base, or we played Stanford lacrosse together, our families have grown up together, we went to each other's weddings. There's such a personal connection. I see this in so many early, mid-stage companies. They won't let the person who's causing the most harm to the business go, but they'll let everybody else go through that revolving door on Mita's team. And so I would argue a lot of times HR is trying to do the right thing, but it's, at the end of the day, not their decision. It lies with the business. And so then you could argue HR can do a better job of influencing and advising, and that's the role that HR really should be playing. And I've seen more and more HR professionals do that. But it's so interesting when I hear people blame HR, and I was like, actually, you should be blaming the CEO.
Ben: But okay, what does it signal? 'Cause these bad bosses are definitely — internally, people know, people on their team and probably others — the worst kept secret. What is it communicating around the organization's culture or values when someone who is so obviously a bad boss remains while other people get counseled out or performance managed out? What does that say about who gets ahead or the values or the culture? Like, what's the lesson that everyone else takes from that?
Mita: Driving the business at whatever cost it takes? Favoritism is really clear. Not everyone has an equal shot to reach their potential. There are definitely people who are protected because they've got personal relationships. I see this, you know, larger companies — because, you know, you're near Fortune 500, Fortune 100, this happens there too. There's just more rules of the road, and people are so scared about the stock price. Let's be clear, it's always, like, what's happening — I mean, we saw what happened recently with the Nestlé CEO. I mean, terminated for having a romantic relationship with the direct report. He didn't even get severance, right? No severance. And you saw what's happening with the stock price there. So in private companies, a little different, right? And so people can get away with those kind of things. But you know, when I coach leaders — if I was coaching you, Ben, and you wanted to hold onto Mita for whatever reason, I would say, you know, is Mita the person who's really going to help get you to where you need to go next with this company? Because usually there's a group of people that have founded the company who aren't gonna help you get where you need to go next. And I could also say to Ben, I know you really care about Mita. Why don't we help set her up for something new that she can do? Why don't we help create a succession plan? And also, oh, by the way, Mita just might need therapy. And I've had these conversations with founders where they've said, yeah, I'm actually gonna talk to this person. It's, you know, hurt people hurt people. Let's stop weaponizing executive coaching. Executive coaching is not gonna help when someone needs therapy, anger management, they need to take a leave of absence. Let's do all of that. And so those are the ways I would try to convince you to think about how do you still help Mita, because clearly you care for her, but also realize that this is hurting the rest of your organization.
Ben: And my therapist, he talks about multiple roles are messy. So, you know, upfront, obviously hiring fewer friends, you know, can keep you out of that. But also I think some executives don't understand that you can give people, like you said, a different role or sort of a softer landing, and alternative things around severance or placement or other things like that. I think everyone just thinks of firing someone as this very kick-to-the-curb thing, which obviously is justified by these behaviors. But if they have this personal loyalty to these folks, I do think thinking about creatively and thoughtfully, you know, transitioning them out in a way that doesn't necessarily destroy the friendship or the relationship — or hopefully doesn't. But I think everyone just resists that, 'cause they have a prediction that's gonna be terrible and they want to, you know, avoid that conflict or avoid that relationship damage. But a lot of it comes, I think, for that executive, as a lack of courage or an aversion to conflict.
Mita: Yes, it is the courage piece, right? But if you can help with the creative solution and landing — and of course, I'll also say there's some behaviors that should not be tolerated, and you should be terminating people immediately. But I say, Ben, where there's smoke, there's fire. None of these things just all of a sudden happened overnight in our workplaces. If I've been bullying people, it's been happening for a while. You can find the breadcrumbs, right? You can find the trail of things that I've done and said. And so that's what I generally have found in this work, that it's not something that this happens — you can go back in time and then see all the red flags you missed.
Ben: I was thinking about, you know, under stress — you mentioned whether it's internal or external stress, within the organization or not — I was thinking of the Hogan assessment. Measures people's strengths, but then under stress they become derailers. So if I might be charismatic, under stress I might be melodramatic. If I might be exacting or detail oriented as a strength, under stress I might be perfectionist, right? I might be, you know, a little bit rule breaking, then I could be rogue under stress. Do sometimes these bad bosses — do some of their maybe bad boss traits actually get recognized by others, who are less close to it, as strengths?
Mita: I love that question, because someone who's a bad boss for me might be a great boss for you. Context, situation matters. And someone might be, I feel like, micromanaging me to death — which is hilarious, 'cause that's my notorious bad boss behavior. I hate being micromanaged, and yet I've done it to others. But you might be a new hire. You might be new to this function, new to the company. You are happy to have some more handholding. And so that's the whole point of behaviors. Like, I talk about myself as a micromanager. I have high standards of excellence. I know what, I feel like, good, great looks like. So that translates into helping, coaching my team on inputs versus outputs and being very clear from the start on what I expect the end product to look like. But to your point, if there's stress, it can go into controlling, perfectionism, redoing people's work, focusing on details that don't matter. And so when you know that about yourself, you can watch how it swings.
Ben: You know, a lot of your work in your prior book around inclusion, Reimagine Inclusion — you know, we think a lot about where people started out in life. You mentioned with Medusa that you'd never been screamed at, right? That was a sort of new experience. But, no, some people grow up in environments or cultures where screaming is a part of figuring out what you're gonna have for dinner. So there's this sort of matching of cultural backgrounds too, in increasingly diverse workforces, that people's maybe cultural norms around a particular way of being could show up and could be viewed potentially as a bad boss behavior — it may just be a different thing. How do you figure out if someone is just a different style versus if someone's actually truly a bad boss?
Mita: I think it depends on the level of hurt and harm, and also it depends on how they receive the feedback when you talk to them about how they're behaving. I think that's really important, and so to weigh those two things, because there's a difference between how we grew up culturally and cultural differences, and how we behave in the workplace and how that's impacting others. I mean, in her case, there was some trauma there, that you think that you can scream and yell at people repeatedly, over and over again. Something's happened in her life where — and you know, in that situation, Ben, I'll say leadership enabled her. Oh, this is just how she works. She's just having a bad day. I mean, this is an individual — I will never forget — she had one team, 12 people turned over on that team in less than 16 months. She goes to lead another team, which I'm forced to join — "voluntold," as I like to say. And what do you think happens within 16 months? A dozen of those people move on as well. And so also the systems enabling the behavior.
Ben: We learn in our careers over time some upward management approaches. We learn that — this often in leadership development or coaching or things like that — and there's obviously the get out, right, strategy of a bad boss: find a different job in the organization or elsewhere. And it's good to always have choice, right? To not feel stuck. But yes, of course, you know, out of sort of empathy and compassion — for some people might live in a geographic area where there's not other employers. They might have a dependent that has special needs and they need certain benefits. They may have certain flexibility structures they don't think they could get elsewhere. And it's important — so what do you say to folks, you know, that maybe aren't in a position to leave immediately? How do they reduce some of that harm or hurt, or how do they create a little bit of distance or boundary?
Mita: Not everyone has the privilege to resign tomorrow, and it's the worst advice that I've ever been given — why are you staying? Get out tomorrow. Like, friends trying to be helpful, but being absolutely dismissive of the situation. And so my advice to anyone listening is, create your get out folder. What does that look like? Have your resume ready. Always have your resume ready. If you get one thing from our conversation today: have your resume ready. I don't care if you're happy, unhappy — always have that ready, and start to plot out companies and people. I haven't talked to Ben in a while — let me reach out to him. And start networking and reaching out to people and thinking about what you wanna do next. But what are you gonna do in the current situation? And so what I'm gonna do is, I'm gonna also try to think about, are there other places and spaces that I can go in the company? We talked about that. How bad is the behavior? If you're working for Micromanaging Mita — I have never thrown anything at anybody at work — and so the level of, you know, my bad boss behavior is probably on the really annoying, micromanaging. And so if Ben's working for me, he's gonna have an expiration date. He's gonna say, I'm gonna do this for six to 12 months. And I'm actually gonna pull up my resume and try doing this exercise: write down all the bullets of what you will have accomplished working with Micromanaging Mita. Like, put that energy towards, if I'm gonna stay, I'm gonna actually make sure I get the things I need to get out of it. And my final piece of advice is, keep rebuilding your confidence outside of work. What happens in these situations is that you'll feel like you start to lose pieces of yourself, and you start to doubt yourself and your capabilities. And so what that means is, outside of work, if you can volunteer in a local community, decide to coach somebody's, you know, basketball team, find a childhood hobby that you left long ago — for me, that was writing, and that's how I got back into it. Discover a new hobby as an adult and do something that continues to spark curiosity. And also just really having a strong sense of self-confidence so you don't lose that.
Ben: And is there any bargaining that people can do? Because I think so often there's this awkwardness, because of the power structure or authority, where people just don't speak to their manager to say, hey, you seem to be very involved in my work and it's new for me, or it's annoying, or it's upsetting. Like, what would I need to show you? Or what would it take for you to give me a little bit more rope? I mean, some of that is — it's not ever decoded or talked about. It's just this, you know, thing in the room that's never sort of discussed. Is there a way to bring it up that doesn't have the person be defensive and say there's something wrong with you, but more about the dynamic between two people?
Mita: This is the art of managing up, which I failed at so many times in my career. I didn't realize you had to manage your boss, and that — ugh — feels heavy. But it's about really how to help your boss work better with you and the team — like, you're just being helpful. And I thought about it that way, which really flipped how I thought about managing up. So I'll never forget the boss who would text me at 6:30 AM, and it was, like, random thoughts or a stream of consciousness about some new project. Or, like, why are you texting me at 6:30 AM? Like, my house is chaos. Doesn't matter if you have kids or not — mornings are sacred for whatever your ritual is. And so what I started to do, Ben, was I would actually not respond over text. I would get into my email at 8:30 and respond. I started to retrain her. But also, I would then in our team meeting say, hey team, I just started a Google Doc where anyone who has new ideas about projects, let's just all go in there, have at it, type in all your great ideas, and let's review them every Friday. Do you see what I'm doing? I'm trying to retrain the boss, but I'm also including the other team members, because likely if this person's behaving this way with me, they're doing it with other people. And so sometimes it can be difficult to have that conversation, to say, Ben, I feel like you're micromanaging me. That's never gonna happen. It's probably not gonna end well. But I also could ask specific questions, which my team once did of me when I was Micromanaging Mita. Can you explain to us why you changed the image on slide three? We noticed on slide 10 you changed the colors on the graph — is there a reason for that? So do you see? Like, yeah, I'm micromanaging. Sure, I'm controlling. I wanted a better image, right? But my team is then acting as a mirror. Because there might be reasons — like, well, the colors didn't make sense, or they didn't pop on the graph, or, you're right, I just like this image better and I should have told you what image I was looking for. And I think whether it's helping retrain the individual or the team, or mirroring back and asking questions, I think hopefully that helps people think, oh yeah, I'm micromanaging here. Like, that's what Ben's trying to tell me.
Ben: I'm just curious — you know, people listening, we talked a lot about, you know, how to deal with a bad boss. I bet some people are wondering, am I a bad boss? There's a lot of insecurity in general I think people have around being a leader or a manager — am I doing a good job? — but they're worried if they're being good enough. But what might be things people could, you know, do or understand to know if they're being a bad boss?
Mita: I think most of us know when we've behaved badly. Okay, I'm not talking about the people who have made the headlines and wreaked havoc on their organizations and need to seek redemption elsewhere. I'm talking about you and me and people listening — most people listening. I think when you've walked out of a meeting, when you've snapped at someone, you've hung up the phone, you've ended the Zoom, and then you sit — and do you have the courage to sit in the silence with yourself and say, I'm gonna trust my instincts here. I didn't behave well. I owe Ben an apology. Most of us know. And so we go back to career journaling. Can you spend 10 minutes a week at the end of your week just sitting down and reflecting on how you feel the week went? I'm not talking about, like, how projects went — how do you feel you showed up? I think there's that piece of, like, how do you cultivate self-awareness? That's how you do it, right? And then the second is, there are likely signs and you're ignoring them. I'm walking into meetings. People seem anxious around me. They seem more quiet than usual. They aren't engaged. I'm the last person to know what's going on in the business. Signs. Exit interviews — do companies even do them anymore? I hope they're not canceled. Exit interviews, when done well — they have really good insights there if you create space for people to tell you what's going on. And a few times in my career I have exit interview notes, and I'm like, wow, I behaved really badly. Like, that's what the person's telling me. And then the third is, are you asking for feedback regularly? And how are you doing that? I mean, I hate, you know, a boss who comes to me and says, Mita, tell me what you think I should be working on. I'm like, you are the boss. You tell me. Like, why are you asking me open-ended questions? And so being able to show a little vulnerability and say, here's the things I'm working on, I'd love your feedback on that — that opens the gateway for me to feel comfortable in a power dynamic. Ben is telling me that he thinks he needs to delegate projects sooner, and he's right, and he's conveyed that. So now I feel comfortable sharing ways in which I can support and help him and help him stay accountable.
Ben: And I hear just this general sense of responsibility and awareness of one's impact on others — that's part of that, you know, reflection and understanding. Because I do think that we do know that moment that we sent that terse Teams or Slack message or email, or we cut someone off in a meeting. But I do think sometimes there's a sense of shame around that, that we don't even want to acknowledge that with others. We have our own private coping mechanism, but we don't repair the sort of rupture that happened in that moment. And I do think there's a lot of things — again, people wanna look good, and when they mess up, they don't look good. But again, that can cause even more stress and exacerbate more bad behaviors.
Mita: And I hope that one of the things we all walk away from our conversation today is that being vulnerable can make you look good and make you a really good leader. I'm not saying that we're doing therapy sessions and I'm not dumping trauma on you in every one-on-one I have. But I'm saying that I say — you know, as I talk about in The Devil Emails at Midnight, I lost my dad suddenly in 2017, and that's when my bad boss phase started. And for me to say, I'm coming into this meeting and I'm missing my dad today, or it's his birthday — and so you have some sort of context on what might be happening for me, versus, like, she's just lost her mind, she's screaming, yelling, and she's disengaged. Right? For us to just show a little bit. Or, like, my kid is sick and he went to school and now I'm thinking he should have stayed home — right? Like, all the things that are running through her head. My dog is sick at the vet, might need surgery — I'm preoccupied in this meeting today. And then people are like, oh, wow, she's being human and allowing us to be human. And then we can still have this meeting and discussion, but now I might understand why she's showing up this way and might not take it personally.
Ben: So as we reframe, it's not bad boss behavior — Mita's just having a human moment, and she's told us ahead of time. I'm having some compassion and empathy for bad bosses. I think I've just often demonized them — and why did we have these jerks or these a-holes, and let's get rid of them. But when you talk about your father passing suddenly in 2017, my heart dropped. And of course that's gonna affect you. But if I just look without that context and say, well, Mita is being a, you know, toxic micromanager — versus if I'm like, Mita's dealing with a major life event that any of us might struggle with — all of a sudden the bad boss is someone I actually kind of wanna maybe take care of or be curious about, versus just someone I want to eliminate.
Mita: Let me tell you, if you had had me on your show five years ago, I don't think I've had this level of empathy for bad bosses. I've certainly gained it on the course of putting together The Devil Emails at Midnight.
Ben: You're teaching me. Now it's time for our Lift It or Ditch It segment. We'll present our guest with a list of hot topics and find out if they choose to lift them and support them, or ditch them and say goodbye. Mita, are you ready?
Mita: Oh my God, I'm buckling up.
Ben: All right. Here we go. Team dinners.
Mita: Lift it — with no pressure to drink alcohol.
Ben: Bosses texting employees.
Mita: Ditch it.
Ben: One-on-ones.
Mita: Lift it.
Ben: Surprise meetings.
Mita: Ditch it.
Ben: Forcing people to go on camera.
Mita: Oh gosh. I don't know. Can I do neutral?
Ben: Yeah, you can do anything you want.
Mita: Neutral. I'm gonna pass.
Ben: Flying on the same flight as your boss.
Mita: Ditch it.
Ben: And side hustles.
Mita: Lift it. I feel like I was on a game show.
Ben: I mean, you were, and I think you won the grand prize. This is amazing. Okay, Mita, thank you so much for coming on the show. I am thrilled that you're able to share with our audience a lot of your experiences, and that you've taught me a little bit of empathy and wisdom around understanding and maybe taking care of bad bosses.
Mita: Oh, thank you so much for having me, Ben. I hope everyone can check out the book, The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses.
Ben: Thanks for joining me this week on The Lift. For more info on what you heard in today's episode, visit our show notes. You can find bonus resources at pilot.coach/thelift. If listening to The Lift today was a good use of your time, please share it with a colleague, a friend — I don't know, your ex, your mother, anyone. Don't let good advice die with you. And for those of you who like to earn a little bit of extra credit, leave a comment on Spotify. We'd love to hear from you. The Lift is produced and edited by the team at editaudio. This episode was produced and edited by Ali Sirois. Our production manager is Kathleen Speckert. Our executive producer is Steph Colbourn. A special thanks to Korey Rich and Beth Gatsik. There's only one way to go: upward.
