On this episode of The Heidrick & Struggles Leadership Podcast, author Mita Mallick joins Christina Cary to delve into the formative leadership missteps that inspired a new approach to studying “bad bosses.” Mita outlines common triggers for negative behaviors, from external market pressures to spillover from personal crises. She pulls back the curtain on her own experience with poor workplace management, including with a leader whose intimidation drove short-term output but degraded culture over time, and a “toxic positivity” cheerleader whose unwillingness to meaningfully address new challenges hindered his team’s professional development.

Reflecting on her own leadership, Mita urges leaders to coach, not control; set clear guardrails and expectations, take ownership of truly matters to you, and explain the “why” behind decisions. She emphasizes peer support via specific, compassionate check-ins and urges leaders to proactively seek feedback.

Welcome to The Heidrick & Struggles Leadership Podcast. Heidrick is the premier global provider of diversified solutions across senior-level executive search, leadership, assessment and development, team and organizational effectiveness, and culture shaping. Every day, we speak with leaders around the world about how they're meeting rising expectations and managing through volatile times, thinking about individual leaders, teams, organizations, and society. Thank you for joining the conversation.

Christina Cary: Hi, and welcome to the Heidrick and Struggles Leadership Podcast. I'm Christina Cary, partner-in-charge of the Heidrick and Struggles Washington, DC office and a member of the Human Resources Officers and Global Technology and Services practices. Today we are joined by author and workplace strategist Mita Mallick. 

Mita has been both a marketing and human resources executive with a strong track record of transforming businesses. Her first book, Reimagine Inclusion: Debunking 13 Myths to Transform Your Workspace is The Wall Street Journal and USA Today bestseller. And I actually had the pleasure of discussing that book with her on an earlier Heidrick Leadership Podcast episode. Mita's latest book, The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses, explores how poor leadership shows up in the workplace and what effective leaders can learn from it. Mita, welcome once again. Thank you so much for taking the time to chat with us. It is great to have you back. 

Mita Mallick: Thank you for having me back. I'm excited to be a repeat guest. 

Christina Cary: What drove you to write a book on this topic specifically? Especially since, I would imagine, it probably required you to reminisce about some less than enjoyable situations and people that you had to engage with. 

Mita Mallick: So, the genesis of the book is—my mother's home was flooded, almost destroyed, pretty much, two years ago. And so here I am in my childhood bedroom, trying to save all these things from elementary school: spelling bee certificates, report cards, book reports, and all these things, and I come across a notebook from my twenties. I had a list of bad bosses: nicknames for them, little vignettes, and things they had said and done. And I've always been a writer, and I've always journaled, but I was sort of surprised to find this, and in such detail.

So as I was driving away from my mother's home, I had this moment where I thought to myself: What if I'm in someone else's notebook? I wanted to take a different approach to the topic of bad bosses. It's really easy to talk about all the bad bosses we've had, but what can we learn from them? What can good leaders learn from bad bosses? That's the question. 

Christina Cary: I'm curious, what are some of the negative leadership patterns that are most common, and are there certain organizational cultures or situations that tend to foster those negative leadership patterns?

Mita Mallick: I really boiled it down to three moments where bad boss behaviors can show up. One is [when] there's something happening in the external marketplace that’s causing pressure on your company. We're sitting in the US right now—lots of conversations around tariffs, what’s happening with the economy, what's happening with AI, competition, all of these things. Bad boss behavior shows up. 

Number two: Christina's working for me, and I'm the bad boss. And this is Christina's first time leading a team. She doesn't have a better role model. It's Mita. And Mita has a lot of bad boss tendencies, and Christina is absorbing those, whether she realizes them or not. 

And then the third is [when] something happens in your life, a personal earthquake. You lose someone you love. You have a miscarriage. You divorce, break up, move. You are sick, someone's sick. I could go on and on. But we can't compartmentalize these things anymore. It's not like I can shove grief in the kitchen drawer and then show up to work and think everything's fine. And when I feel any kind of loss of control in my personal life, what's the easiest thing to do? I show up at work and try to control my team because, sometimes, they have no choice.

Christina Cary: Talk about one of those bosses. You reflect on a lot of them in the book, but is there one in particular who had a particularly negative effect on team dynamics, or on you in the short term or in the long term, and what did that boss teach you about leadership?

Mita Mallick: The one that I still can't wrap my head around years and years later is Medusa. I do nickname all my bad bosses. There was nobody in my life, not my parents, not my husband, not my brother, and I certainly didn't tolerate this behavior from friends—no one ever screamed and yelled at me, until I showed up and worked for Medusa. She publicly and privately humiliated people. She was the equal-opportunity toxic bully, meaning some bullies will isolate and have a team. They try to divide and conquer. She went after everybody. She had tantrums like a toddler. She would routinely throw pens across the table. When she was frustrated, she threw a Chanel shoe at a colleague.

And this behavior continued on and on. It's like the system enabled her. But what was really interesting was, here's what I learned: Fear drives short-term results. It does. I showed up at work scared every day. The analogy I would use is when I hear there's a black bear in the neighborhood on some WhatsApp group: Something's happening! “Oh my god, it's on the neighbor's deck,” “Oh my god, it's on our deck.” And that visceral reaction you have, it's this adrenaline rush. You're going to fight or you're going to run, right? What are you going to do in that moment? 

And so that's the feeling every day that was happening at work. And I was working really hard, because I wanted her off my back, wanted her to like me. I wanted her to recognize the things I was doing, and I thought if I could just outwork the bully, she would leave me alone.

It didn't matter. She was going to come after me anyway. So then what happens? Fear kills culture long term. Because what ends up happening is that I'm tired of being scared. I'm tired! It's exhausting! And then I'm like, it doesn't matter. So let me just go under the radar. Let me do a little less. It's like the candle analogy I use when the flame starts to flicker out—that happens with us. You're like, “I don't even know why I'm here anymore.” So that is the biggest lesson. And it's the same story I see happening over and over again in so many teams and organizations. 

Christina Cary: Wow. You've talked about challenges that you've had as a leader yourself. It sounds like you talk about yourself as a bad boss in the book. How did you realize that? Was there a tipping point or a specific instance where you said, “Oh man, I need to make some changes,” and then how did you shift your approach going forward? 

Mita Mallick: I was a notorious micromanager. I can say that I had really high standards and that I wanted things a certain way, all the things we say to ourselves, but it was that I thought I was supposed to do my team's job for them. I didn't understand that I was supposed to coach and teach them.

I'll never forget, there was this one instance where I'm sitting with my team and they very thoughtfully asked me a series of questions. We’re looking at a deck, and they said, “Could you explain to me why you changed the image on slide two?” “Can you explain to us why you changed the colors on the graph on slide seven?” What was I going to say? That I am just obsessed with images and I needed to get it right? That was it! There had to be the perfect image of a woman washing her face, and I had to pick it. 

I'll never forget that story because what I think about now is that if there are things that you must do yourself, if there's something like an image in the deck, or something you're working on for a client proposal, then as the leader, own that part and say, “I'm going to take on A, and I'm going to give you B, C, and D. Let me tell you the guardrails, the guidelines. There might be a template. I know the client likes to see it this way. We need to include the data in the appendix.” Whatever it is, give them all of the guardrails upfront so that you're very clear on the output, and that's what I got better at doing over time.

Let's say we're working together, and you shoot me over the client proposal, and we had already aligned on the inputs, right? I spend about 45 minutes redlining the whole thing, and I write back and I say, “Christina, thanks so much. See my edits.” And you receive that and you're like, [this is] devastating. In the moment, you're like, “What is this? The whole thing is redlined.” Versus me getting on a call or writing to you and saying, “Christina, this is a great first draft. I wanted to go through it. Now having had the week to think about it and talk to some of the other partners, there are some things we know that this client wants. And so I want you to understand why I redlined, or, even better yet, can I sit down with you with the document and talk through it? Not go through every line, but sort of talk about the themes of why I redid things.” And that's coaching. That is coaching and teaching versus micromanaging. 

Christina Cary: Absolutely. Is there one bad boss behavior that we don't really talk about enough, or maybe isn't as obvious as some of the ones that you've already mentioned?

Mita Mallick: One of the ones we don't talk enough about is the boss who was filled with toxic positivity. This boss, I nicknamed him the cheerleader. He was the corporate pied piper, Christina, in a time where people are trying to get people back into the office. You wanted to be in the office to be around him. He was funny, charismatic. He took the time to teach you, invited you to meetings and events. You're like, “Well, what's the problem, Mita? This sounds like a great bond.”

But [he] was surrounded by yes-people. And I'll never forget this one business example: We were working on this really great cereal innovation. It was going gangbusters; people are buying cereal for breakfast, lunch, and dinner, and it is doing so well. Of course, what ends up happening? We can't find the ingredient, like the key ingredient. Our supply chain people have told us it's not available for the next three months.

I know many people listening to this can relate to this, right? Something's happening in the market, and we can't get a hand on this, but customers are demanding it. It's flying off the shelves, right? And so we tell the cheerleader this. We're like, this is a situation. 

[He replies,] “We're going to add a million dollars to the forecast. Don't worry about it. We'll figure it out. I believe in you! What doesn't kill you makes you stronger! Go team!”  And it's the constant Instagram reel where suddenly you're like, “No more rainbows and lollipops and cotton candy. I am exhausted by this lack of grounding in reality.”

Christina Cary: We need to acknowledge the real situation here. 

Mita Mallick: What do you think happens? Fast forward: we missed the forecast. Of course, we're never going to make the million-dollar forecast. We couldn't produce the product! And so, I'm sitting in the performance review, and I get no merit increase. I get barely a bonus that covers my Starbucks obsession, not even. I get a low rating, and the rationale is, “Well, you missed the forecast.” And I'm like, “Am I in the twilight zone? We told you we couldn't make this forecast, right?” This is really dangerous because what's happening in this market right now is goals are constantly changing.

So can we be grounded in reality and say, “Okay, rather than the 100 percent, can we get to 70? Can we get to 80? What's it going to take?” But too many bosses will have their heads in the cloud and be like, “Oh, you’ll figure it out.” It's like, no, we're not going to figure it out. We need your help to reset the goals and help us figure out what the new measure of success could look like in this moment. 

Christina Cary: When a peer is struggling as a leader, someone that you work with closely, are there specific things you think other leaders can do to offer support and guidance without seeming as though they're trying to insert themselves in the situation? How can we lean on each other to grow, to improve, and move forward? 

Mita Mallick: If you have a close relationship, if it's Christina and Mita working together and Christina's seeing me struggle, she could take me out to coffee and just say, “Just want to check in on how you're doing this week. I noticed in this meeting you seemed pretty irritated; your face was red and you dropped an F bomb.” Can she sit down with me and act like a video recorder, just sort of play back the things that she's seeing? And if we have a trusted relationship, I'm going to say, “You know, I'm really struggling. I went from [managing] 10 people to 20, and now I have two different areas of responsibility where I'm not finding much synergy. Thanks for asking.” And then Christina might say, “You know, that happened to me a few years ago, and here are some of the things I tried,” or “Here are some of the things I'm doing, and I'm happy to check in with you once a week.”

I think so many of us see people struggling in the workplace, right? And I wish we had more courage to intervene and just ask the question. Because Mita is struggling—Mita knows, most of us know—but she's trying to push through it, not work through it. She's trying to push through it. But with Christina, if she can come and be a mirror, I can start to work through it.

Christina Cary: What are some of the pieces of advice that you'd give a leader who thinks they have room for improvement, and has actually acknowledged it and said, “Hey, sure. I know I have issues with respect to my style, with respect to how I engage with the team.” What are some of the tips and tricks you would say to those individuals?

Mita Mallick: I would say ask for help. And this is not something we've been born and raised in corporate America to think about. Leaders are at the top. You got to the top for a reason. And I know a lot of this has changed, but there are still leaders who are afraid to ask for help because of it making them look weak or vulnerable to their teams.

I think we need more vulnerability in the workplace. If Christina was on my team working for me, and let's say we were having coffee on Friday, here's an approach I might take: I might send her a note saying, “Christina, I'm excited to catch up with you on this client and the status on Friday. I also wanted to let you know I'm working on delegating proposals faster, and I'd love your advice and feedback on that. That's something I want to work on this year. See you Friday.”

There are a few things I've done: One, I've taken accountability for the thing I want to work on, and I'm sharing it with you, right? So I'm modeling vulnerability by sharing the thing I need to work on. Two, I'm putting it in writing. Now, this is important. I'm giving her time to process it in advance and not putting her on the spot, so she has time to think about it. And then three, depending on the culture, I might not use “feedback.” I might use the word coaching.

Isn't that interesting? In some cultures, feedback can feel heavy, rather than saying, “Christina, I'm just looking for some coaching on this thing.” And then when we meet, Christina might say, “I actually think you're doing that quite well. May I offer something else?” I say, yeah, sure. Go ahead. And then my job there is to say, “Thank you so much for sharing; I really appreciate it. I'm going to process and get back to you.” Because not all feedback is meant to be accepted; context, situation matters. I've gotten a lot of feedback in my career that I haven't thought was very fair, and then there's been feedback that's been really good, and I just wasn't ready to hear it.

So you want to take the time to process and then come back with a plan to say to Christina, “I actually really liked what you offered. I'm going to work on this, and I love that you feel comfortable to hold me accountable.” Or I go back and say, “You know, I appreciate that you shared this. I'm going to go back to working on the original thing I wanted to work on. And I'm going to revisit your piece of feedback in the next six months.”

Christina Cary: Yeah, I mean, we talk a lot here at Heidrick about being willing to have that courageous conversation, right? And making sure, also, that the person you're speaking with is ready to receive the feedback. Because if they're not ready, oftentimes it's going to fall on deaf ears, and also, it could potentially backfire, right? So, assessing the situation. But then as you said, being vulnerable as a leader and as a boss and willing to acknowledge your faults and what you need to improve on can just go such a long way with your team.

Well look, I am super excited to read the book, and I just can't thank you enough for coming back for a second time. Really appreciate your guidance

Mita Mallick: Thank you for having me. I loved being on the show and I can't wait to hear what you're going to start working on in terms of your own leadership style. So thank you. 

Christina Cary: Amazing. Thanks so much, Mita.

Thanks for listening to The Heidrick and Struggles Leadership Podcast. To make sure you don't miss the next conversation, please subscribe to our channel on your preferred podcast app. And if you're listening via LinkedIn or YouTube, why not share this with your connections? Until next time.

About the interviewer

Christina Cary (cbcary@heidrick.com) is a member of the Human Resources Officers and Global Technology and Services practices; she is based in the Washington, D.C. office.