Strategies for Dealing with Difficult Coworkers

ALISON BEARD: Welcome to the HBR IdeaCast from Harvard Business Review. I’m Alison Beard.

Work can be challenging for lots of reasons; deadlines to meet, bugs to fix, profit margins to hit. But most of us have probably come to realize that what makes or breaks a professional experience is people. We all have our own strengths and weaknesses, our own habits and hangups, and we’re lucky if we find colleagues we gel with. Invariably, though, you’re going to encounter a boss, peer, or direct report that isn’t at all fun to work with. They’re very difficult.

Today’s guest has spent a lot of time thinking about the best ways to deal with these kinds of coworkers, how to identify them, engage with them and how to manage yourself through the conflict. Amy Gallo is a contributing editor at HBR. She wrote the new book Getting Along: How to Work With Anyone, Even Difficult People and the HBR article, “How to Navigate Conflict With a Coworker.” Hey, Amy.

AMY GALLO: Hi Alison.

ALISON BEARD: So happy to have you on the show.

AMY GALLO: I’m happy to be here.

ALISON BEARD: You are not a difficult coworker. You’re one of my favorites.

AMY GALLO: Thank you. And likewise. I never find you difficult.

ALISON BEARD: So in a world where we are increasingly trying to not label people, can we really pinpoint certain individuals as being “difficult”?

AMY GALLO: Oh, I’m so glad you asked this first because I have mixed feelings about the use of the archetypes in the book. There are eight archetypes. They are personalities that we all recognize: the passive aggressive peer, the biased coworker, the insecure manager. However, I don’t want people to use them as a pejorative label that really either tries to diagnose someone or distance yourself from someone. They’re meant to be a tool to help you get the advice you need for your specific situation. They’re meant to be an internal usage, not something you say out loud.

ALISON BEARD: And to not put the colleague into a box that says, that’s all you are. You’re only a know-it-all. You’re only a passive aggressive person.

AMY GALLO: Exactly. That’s where the confirmation bias can be really dangerous. If I decide Alison’s a know-it-all, every time you say anything with any sort of confidence, I might say to myself, “Oh, there’s the know-it-all behavior.” And that’s why it’s important to be open to change. Ideally, you’re engaging in a conversation with this coworker because you want a more positive relationship, and being so certain that you’re seeing it the right way and they’re seeing it the wrong way is only going to lock you into position and not give room for the dynamic to change.

ALISON BEARD: And so you seem to be suggesting that each of these types need to be approached in a different way. There is directed advice, but is there also some common advice?

AMY GALLO: Of course, yeah. There is a lot of general advice that works regardless of what category people fall into or if they defy categorization together.

ALISON BEARD: Let’s start with common advice first. What’s a first step?

AMY GALLO: The first real principle to keep in mind is that your perspective is one perspective. It’s easy to say, “Oh my gosh, they’re a know-it-all, they have no humility whatsoever. I just can’t stand working with them. Their behavior’s totally inappropriate.” That’s just going to lock you into a negative dynamic. You have to remember there are many different perspectives involved in this dynamic. There’s yours, there’s the other persons, there’s people outside that dynamic who are observing it. And that helps you to open up to different interpretations of the behavior.

I remember years ago I was complaining about my husband wanting to go surfing during a blizzard. We had an infant. I was like, “What? Who does that? Who goes surfing?” And my friend said, “Well, your husband does.” And I thought, “Okay, yeah. For him, that seems like an appropriate thing to do.” And I think that’s the kind of attitude you need to have with your difficult colleagues is, think about yes, this may seem inappropriate. It may even be causing some harm for you and for others, but in their head, there’s probably a rational explanation for what they’re doing. And your goal is to figure out what that might be, to figure out a way of interacting that’s much more healthy and productive.

ALISON BEARD: Yeah. As we’ve discussed before, I think we have very similar husbands. But so this step at looking at yourself critically, making sure you’re seeing the issue from the other person’s perspective, particularly when you don’t like them, or it’s just very clear to you that they’re not behaving appropriately in a workplace setting, what advice do you have for people getting over that hump to a place where you can honestly say, “Okay, I see where they’re coming from and actually, maybe I’m part of the problem too.”

AMY GALLO: Mm. I think one of the best pieces of advice I can give around that. When you start to feel that way, and when the person’s really being a jerk, it’s hard to get over that, is to find someone who likes working with that person. Chances are there’s someone in the organization who either feels positively about them or at least neutrally. And I would go talk to them and not in a gossipy like, “Oh, don’t you hate Adam too?” More of “I’m struggling with Adam. I’d love your advice about how you work best with him.”

They might say, “Well, he’s really brusque in email, but once he get to know him…” Or “He’s insecure so he often talks about himself and his accomplishments, but he’s really invested in the team’s success.” Someone who can give you a little bit of a different perspective. I think that’s one tactic that can help you get over that.

The other is to really think about: use empathy. Think about what pressures they’re under. Are they new to the organization? Are they in a part of the organization that feels less valued than other teams? Try to really put yourself in their shoes. That’s a strategic tactic that helps you unhook from the story you’re telling yourself about how horrible this person is, to maybe open yourself up to a different narrative around how you all interact and how you both might be contributing to the dynamic.

ALISON BEARD: Is your advice any different based on whether the person you’re dealing with is a direct report or a boss or a peer? Do you need to handle each situation differently just like you would handle the different types in a different way?

AMY GALLO: The advice generally works across whatever the reporting relationship is with the other person. However, which tactics you choose to use and how you implement them will be slightly different. With a peer, you’re probably just going to implement these tactics very straightforwardly, not have to think much about the power dynamic. With a direct report, you have to keep in mind how much power you wield over them in terms of what assignments they get or what their salary is.

And with a boss, you have to do the risk assessment of, is it worth pushing back on this behavior? Is it okay for me to be as direct as I want to be? Do I need to maybe be a little more subtle in my feedback or my requests for their behavior change? Because you don’t want to damage that relationship. It’s an important relationship, and in many organizations, that hierarchy will require that you not directly confront them.

ALISON BEARD: A lot of times the advice you hear is to have a frank and open and collaborative conversation about it. But how do you decide on the right timing for that, the right tone for that? How exactly do you do it?

AMY GALLO: Yeah. A lot of the advice I share is about not being direct, actually trying to find ways to sort of nudge them to productive behavior, partly because some of the archetypes I explore in the book, like the know-it-all or the insecure manager, don’t respond well to direct confrontation. That said, you know me well enough to know I’m a fan of the direct conversation, the collaborative conversation. You do have to do the risk assessment of what will happen if this goes sideways, if they get really defensive, if they get upset, if I get upset? But at the same time you want to do the risk assessment of what if I don’t do anything?

That’s the first thing is really be clear with yourself about the costs and benefits of that conversation. And then set it up for a time and a place where you can be your best self and they can be their best selves.

Because we often, or at least I should say I often think about, “Well, how do I catch them? How do I get them in a moment where they’ll hear everything I have to say and admit they’re all wrong?” But you don’t want them to be in a poor frame of mind because then it won’t be a productive discussion. Think about when are you both going to be the least stressed out? When are you both going to be not in a rush? When are you going to both be hopefully slept and in a good mood?

After a productive meeting where you and the other person maybe agreed on something, that’s a great time to sort of pull them aside and say, “Hey, can we chat about how we’ve been interacting lately?” Or “Can we chat about what happened in the meeting last week? I thought this one went well, but there were some things that happened last week that I really want to bring up with you.”

ALISON BEARD: Is that really the right strategy? You’re progressing, and then you’re like, “Oh, but let’s talk about all of our problems.”

AMY GALLO: I mean, it’s a good pushback. Because on the one hand, if things are going well and you think they will continue to go well, and you can let go the past bad behavior. Great. Right? That’s path of least resistance. I love that. However, if you suspect that they’re going to do it again, or things are going well, but you’re worried you’re not going to be able to let go the resentment you have about their behavior, you don’t want that to leak out later. So I do think it’s good to bring it up. And when things are positive, they’re going to be much more open to hearing from you. I’m not promising, it’s going to go a hundred percent easily, but they’re more likely to hear you.

ALISON BEARD: Yeah. Let’s dig into some of the archetype-specific advice. I’ve heard you mention the know-it-all, the insecure manager, and the passive-aggressive peer a couple of times. Maybe those are the most common and we’ll tackle those?


ALISON BEARD: Okay. What’s something that you would do with a know-it-all that you wouldn’t do with the other types?

AMY GALLO: One of the things you have to remember, is that the know-it-all is the overconfident person. We all tend to be overconfident at times. One of my favorite statistics about this is how many people actually think they’re better than average drivers. It’s something like 76%, which obviously is statistically impossible. So overconfidence is normal. It’s something we all experience. And so you’re trying to make sure that, that overconfidence doesn’t outshine you, doesn’t harm others either.

Oftentimes the know-it-all is the classic, “I blow your candle out so mine shines brighter.” And the first thing you need to do defensively is make sure that your good work is known. Oftentimes the know-it-all will take up the airtime in the room. And so you need to make sure you have the space and the visibility that you need.

This is a strange piece of advice, but I’ve seen this work many times, where you actually ask them for advice. It sort of incurs an altruistic mode for them to, “Oh, I can help someone. Someone wants to actually hear from me.” Now, of course, they might go right into proclamation mode and you’ll have to be willing to tolerate that. But by asking for their advice, what we know from research is they’re more invested in your success.

I also think with the know-it-all you do have a little bit more leeway to push back. And that’s because of that overconfidence. You’re not going to really damage their ego like you would with a insecure manager. So with the know-it-all, you have some room to say, “Oh, what are the facts and data you’re basing that on?” Or, “Huh, you seem really sure of that. What makes you know that?” And you have to take the snark out of your voice. You have to really do that neutrally, which is hard. But sometimes pushing back and doing it over and over, shows that you’re not going to just let them tell you that the product is going to fail or your customers aren’t interested in that feature.

ALISON BEARD: Yeah. Okay, let’s turn to the insecure manager now.

AMY GALLO: Yeah. So the insecure manager, and I hate giving this advice, but we know from research it works. Oftentimes you have to flatter them. And it’s the last thing you want to do, because there’s so many costs of working with an insecure manager. Your team may not be getting the resources you need. They may be making you look bad, so they don’t feel as bad about themselves. The last thing you want to do is tell them they’re great. But we do know from research that soothing their ego, calming, what research is called ego defensiveness, tends to make them better managers. They’re more open to your feedback. They tend to be more collaborative.

Important caveat here. It has to be a genuine compliment. So if they’re terrible at being organized and that’s what’s really causing a lot of problems for the team, don’t go in and go, “You’re so organized,” and hope that’s… They’re going to know right away that that’s false. So find something that they do genuinely well, often flattering them in front of other people, people they care about, whose opinions they care about, can be really helpful. It can be a tiny bit soul crushing to have to do that. But we know, again from research and what I’ve seen in practice, is that it really does help that person just be in a better frame of mind.

ALISON BEARD: And maybe helps you because you can focus a little bit on the positive?

AMY GALLO: Exactly. It helps you actually search for what’s actually good about them. Because of the costs, we’re so focused on the damage they’re causing or the inconvenience or the stress they’re creating, but it helps you, like you say, see the positive. And even if it’s like, “I like your shirt.”

ALISON BEARD: You have a good fashion sense.

AMY GALLO: Exactly. I mean, it can help again start to create a stronger bond between you two, and then they can come rely on you.

ALISON BEARD: Okay. Last one we’ll do passive-aggressive colleague. I know that so many people struggle with this.

AMY GALLO: Honestly, this is the question that made me write the book, is that when I wrote the Guide to Conflict and started doing talks and workshops, inevitably someone would ask at the end… And I still happens. I can count. It’s usually the first, second, or third question is someone says, “How do I deal with someone who’s passive aggressive?” And it’s one of the most vexing archetypes to deal with, because it feels like shadow boxing. It’s so slippery. It’s hard to land. Even if you try to be direct, sometimes they’re like, “Nope, everything’s fine.” Right?

Two things I will say about the passive-aggressive peer, is that oftentimes that behavior, again, which all of us exhibit at times, I actually know I did it even this morning, we all do it at times, is that often it’s based on a fear of rejection, failure, conflict. And so if you can do anything to make them feel less afraid, so show them it’s okay to have disagreements, show them that you’re not going to reject them, that can help a lot.

And oftentimes you can do that by focusing on the underlying message, rather than the sort of snarky wrapping around that message. So rather than focusing on the tone they used, focus on, “Well, what is it they’re really trying to say?” And then do something called hypothesis testing, where you say, “Well, I heard you say this. Is that right?” And that shows them it’s okay to actually be direct about what you’re thinking and feeling.

Another thing I’ve seen work, especially in a team context, is passive-aggressive folks tend to respond well to positive peer pressure from a group. Not necessarily from an individual, but if you can set team norms. So as a team, what do we want to agree to? What are the ways we’re going to interact? And one of those might be, if you commit to something in a meeting, we’re all going to write it down, we’re going to follow through. If you don’t, you come to the next meeting with an explanation for why. Or it may be that we spend five minutes at the end of a meeting discussing what we wished we had said earlier, but felt afraid to. That can give, again, that passive-aggressive person a little more space to feel more comfortable.

ALISON BEARD: And you talk in the article also about setting realistic goals. So trying all of these interventions and then trying to figure out what place you want to get to with the relationship. Talk a little bit more about that, why it’s important and what you mean by realistic.

AMY GALLO: Yeah. Setting a goal for the relationship in general is just a great idea. Because I think when we’re stuck in an unhealthy interaction with someone, or a pattern of interaction, we get really focused either on being right or showing them how bad their behavior is. If I go into a conversation or an interaction with a colleague, would that being my goal? I don’t really have anywhere positive to go. Either I win and they lose, or they just feel bad. So setting a goal, like, “I want to not cringe when I get an email from this person,” that can be a real-


AMY GALLO: Low bar. Low bar. But I think it also gives you a sense of progress. Because what we think we want is, “I just want everything to feel fine with them. I want to get along with them.” And sometimes that’s not realistic and it’s a long road to get there. So you need to break it down into goals you can actually achieve.

You might also choose a goal of, “I’m going to try three tactics for the next six months and see which ones work.” Or, “I am going to make sure that my boss doesn’t speak negatively about me in front of others. I’m going to focus on how I can curb that behavior,” rather than, “I’m going to make them a better person.” I have tried that, by the way, trying to force my colleagues to be different people. And it just doesn’t work.

ALISON BEARD: What happens though, if you set realistic goals, you follow all the general and specific advice that you’re giving, and there’s just no change?

AMY GALLO: You quit. No, I’m kidding. I jokingly say that, but I want to actually address quitting, because I think sometimes people think, “I work with this awful person. My work life is miserable. I don’t want to be around them.” And I think quitting is both an overrated and an underrated option. It’s overrated in that there are going to be difficult people everywhere. So sometimes the enemy you know is much easier. But it’s also underrated in that I think people shouldn’t stick around in these relationships, especially if they’ve tried in good faith some of the tactics, they’ve given it time, they’ve really addressed the way they’re contributing to the dynamic. It’s not worth going to a workplace or spending time with colleagues every single day who are causing you like physical, psychological, emotional harm. And so quitting is an option, but you have to try several things before you get there. So, if nothing else fails, you also have the option always of escalating. So can you bring it to someone who might actually be able to do something about it? And in some cases that might be HR or your manager or someone who this person just trusts and is willing to follow their guidance. But one of the keys there, and I really caution about going to HR because you want to choose someone to escalate to who actually has the interest, the motivation and the skills to intervene. It’s rare that people in organizations actually have those skills. So you have to really think about, will this help in the end or will it just make me feel better to have set it to someone in power?

I think another tactic, if you’ve tried everything and you’re really not making progress is to really set clear boundaries, and those might be very specific. So I deal with a colleague who’s a pessimist all the time and every time I interact with them, their negativity just brings me down. So I’m going to set a time limit of, I will talk to them for five minutes, no more, get what I need get out. That might be one tactic. Or I might decide every time I interact with them, I’m going to go find my work BFF and chat afterwards so I feel more positive after that interaction. Or you might decide, I only want to interact with this person over email because face to face is just too difficult or vice versa. But setting boundaries so that you aren’t getting the negative effects of that relationship even if you can’t change the dynamic, if you can lessen the negative impact on you, that’s going to help you a lot.

ALISON BEARD: Okay. So now here is the really tough question. What if you are the difficult person, like how do you figure that out and what do you do about it?

AMY GALLO: So when I handed in the manuscript for this book, I think it was 50% longer than it was supposed to be and every chapter included this section. If you are the passive aggressive peer, what to do. If you are the insecure manager. It makes me so sad we had to cut them out because I do think it’s really important that people recognize that sometimes they are that archetype, they are exhibiting that behavior, and yet it is so hard to see that. I do think reading the common behaviors at the beginning of each chapter will help you see of like, ooh, do I do that? Does that sound like me? And if you suspect it does, ask someone you trust for some frank feedback, someone who’s going to really tell you how it is. And think back on your reviews, think back on the feedback you’ve gotten, does it all add up to some of this difficult behavior?

If so, first of all, you’re in great company. We’ve all been there. We’ve all been that difficult person on the team or in an interaction. So don’t beat yourself up, have some self-compassion of we’re not always our best selves. We all bring baggage into our workplaces, into our relationships. And then start doing a little bit of experimenting the same way you would, if you were trying to improve your relationship with someone else. Think about, okay, if I’m passive aggressive is it because of a fear of failure? Is it a fear of conflict? Is it a fear of rejection? What can I shift in my consciousness or in my work interactions that will help assuage that some? Or are you being insecure because you’re concerned people are going to find out you’re not as qualified as you have projected yourself to be? How can you take steps so that fear is no longer a risk? How can you make clear what you’re capable of and what you’re not in a way that makes you more comfortable in the way you interact with your coworkers?

ALISON BEARD: Yeah. And if I’m a manager of a team, how do I keep an eye out for these difficult people on the team, conflicts between teammates and try to facilitate solutions or should I be more hands off and empower people to do it by themselves?

AMY GALLO: I definitely think the latter in terms of empowering people to do it themselves, the more you intervene, the more you will need to intervene. Because people will say, oh you solved this problem for me last time, I have a new problem you can also solve for me. So as much as you can, let them or empower them to resolve it themselves the better. That said, you should be keeping an eye on the dynamics and asking people, how’s it going, working with the team? Do you have any concerns? And hearing those people out. I think oftentimes managers fear hearing about problems they don’t know how to solve. And sometimes just listening to the problem helps with the solution. And you actually don’t have to have an answer, but you can take steps to do many of the things we’ve talked about.

ALISON BEARD: Yeah. And what can be done about difficult people on the organizational level?

AMY GALLO: Oh gosh, there’s so many things. I mean, I think number one, creating a culture that does not tolerate these bad behaviors. Meaning, people it comes up in their performance reviews. There are team norms that really guard against some of the behaviors. People who are very productive or high performing, but don’t treat others well. Make sure those people are not continually promoted over and over, because then you’re saying it’s okay to be a jerk. So I think you really have to create a culture consciously in which these behaviors are not tolerated. And you might name the specific behaviors. We do not tolerate micromanaging, passive aggressive behavior, mansplaining, right? You might be make very clear, this is not what we tolerate. Or you might say, “As an organization, here’s how we treat each other.” And positively describe how people will interact. We often tell people the goals, we want them to achieve, the targets they need to reach, but we don’t describe how we actually want them to interact with their colleagues. And some people need it made explicit for them.

ALISON BEARD: Okay. This is a fun one. Who has been your most difficult colleague ever? You don’t have to name names. Pseudonyms are fine. And how did you deal with them?

AMY GALLO: Okay. So one was a boss, and everyone told me, “She’s not the easiest to work for.” And I was like, “Yeah, whatever. I can deal with anyone.” And I was in that job, I think it was three months, maybe even less before I was like, “Oh, I can’t do this.” She micromanaged, she talked badly about other colleagues, which I had to presume she was also talking badly about me. Her expectations were wildly unreasonable. She had the attitude of, I made all these sacrifices in my career. You should make the same ones. And I was not ready to do that and didn’t even feel it was necessary.

And I’ll tell you, my instinct was to quit, but I’m glad I didn’t. I ended up tolerating a lot of the behavior, setting a lot of boundaries. She was someone who would email at 6:00 PM with five requests. And then at 8:30, the next morning be like, “Did you get those things done?” And so I had to really decide, I was … I would just respond back, “No, I will get to them this morning. Here’s when you’ll have them.”

I really set boundaries around listening to her talk badly about other people. I had to make clear, I was not going to do that. Partly by either countering what she said with some more positivity. So if she said, “Oh, I don’t think anyone” … there was one person she’d love to say, “I don’t think she did anything yesterday.” And I would say, “Oh no, actually I saw her in this meeting. She sent me an email.” I would sort of just try to counter it.

And that sent the message, I’m not going to listen to this and just hear it out. And I lasted, I think 18 months in that job. I still left because of her. We never became best friends. I’m sure she’s going to read the book and-

ALISON BEARD: Know exactly who she is.

AMY GALLO: Know exactly who she is and think, “Oh, wow. Okay. I guess we’re still not friends.” So, that was how I dealt with that one. At the end of the day, I felt like I behaved in line with my values. And I think that’s one of the most important things you can do, because these people often trigger the worst in us and we say and do things we regret and then you’re not happy about it. And then that just makes a bad situation worse for you.

ALISON BEARD: Yeah. Amy, thanks so much for being on the show.

AMY GALLO: Thanks Alison. This was fun, as always.

ALISON BEARD: That’s Amy Gallo, contributing editor at HBR. She wrote the book Getting Along: How To Work With Anyone, Even Difficult People. And the HBR article, “How to Navigate Conflict With a Coworker.”

If you like today’s episode, we have more podcasts to help you manage yourself, your team and your organization. Find them at or search HBR in Apple podcast, Spotify or wherever you listen.

This episode was produced by Mary Dooe. We get technical help from Rob Eckhardt. Hannah Bates is our audio production assistant and Ian Fox is our audio product manager. Thanks for listening to the HBR IdeaCast. We’ll be back with a new episode on Tuesday. I’m Alison Beard.