How to manage a difficult relationship with your boss

Hosted by Drew Adamek

The relationship with your boss is critical to your career; a good boss gives you the tools and opportunities to grow and advance, while a bad boss can hamper your development and breed resentment. But no matter what kind of relationship you have with your boss, it’s important to take responsibility for your career and find ways to navigate challenging relationships. In this podcast, Karen Dillon, a former editor with Harvard Business Review and author of the HBR Guide to Office Politics, offers several tips on how to thrive even in difficult relationships with your boss.

What you’ll learn from this episode:

  • Why the phrase “office politics” gets a bum rap.
  • How to develop a team mentality with your co-workers, even if you work remotely.
  • Ways to get to know your boss better and strengthen your relationship.
  • Strategies for navigating bosses who hold you back, steal credit, or play favorites.
  • Why you are ultimately responsible for your career.

Play the episode below:

To comment on this podcast or to suggest an idea for another podcast, contact Drew Adamak, a
JofA senior editor, at


Drew Adamek: We've all had difficult bosses, someone who holds you back, hogs all the credit, or plays favorites in the office. But encountering a bad boss doesn't have to make or break your career. You can take charge when your boss doesn't.

Hello, and welcome to the Journal of Accountancy podcast. I'm Drew Adamek, a senior editor with the Journal of Accountancy, and today I'm speaking with Karen Dillon, a former editor with the Harvard Business Review and author of the Harvard Business Review [Guide to Office Politics], about tools and techniques for developing and managing a relationship with a difficult boss, taking responsibility for your career, and seeing the world through your boss's eyes.

Karen, thank you so much for joining us.

Karen Dillon: It's a pleasure. Thank you for asking me.

Adamek: When we talk about office politics, what's the difference between playing office politics to win and engaging office politics in order to survive and to keep your job, and is it possible to just sit office politics out?

Dillon: Well, I don't think so. I think that the phrase “office politics” often connotes kind of nasty backstabbing, the worst instincts of people to be competitive with each other and keep their colleagues down. But I actually think office politics are present in every environment, and it really should mean just referring to having a strategy for dealing with people. You work with people. Unless you are literally writing a book alone on an island and there's no one around you, you have to work with people and you need a strategy to work with people, and that's inevitable for all of us.

So, no. I don't think it's possible to sit it out because we all need to have a good strategy for dealing with the colleagues, and clients, and customers, the people around us who are essential for us getting our job done.

Adamek: What's the biggest, as you see it, misconception that people have about office politics?

Dillon: Well, I think most of us are affected by it. If you look at the data, there's a giant number of people that are upset by what they describe as office politics. Think about how many of us come home and complain about somebody at work who did something to us, or unfairly got credit for something, or in some way is a favorite of somebody. We bring it home with us. It surrounds us and it feels so enormous, and the biggest misconception, I think, is that we can't do anything about it. We're just unlucky. We have the wrong boss, the wrong colleagues. We're in the wrong job. And I don't think that's true. I think we have a lot more control than we think if we have a healthy attitude towards dealing with it.

Adamek: So let's start with the most politically important and probably sometimes fraught relationship that you have in your job. How do you identify what kind of relationship that you have with your boss and how do you start to evaluate the relationship between you and your boss?

Dillon: Well, it's a very important relationship, as you said. It can be one of the most significant relationships in our lives because we'll spend so many of our waking hours at work, so many of our weeks at work, it can become as significant as a family member or a very close friend. That person is very present in your life. So what you hope is that you have a healthy relationship with your boss, you have a boss who is supportive, who you like, who you enjoy working with, who sees the potential in you, and invests in you, and respects you. That's the best-case scenario, a boss who is going to be a catalyst for you going on to greater things.

Unfortunately, bosses are human, too, and even with the best intentions, bosses oftentimes aren't many of those things because they're worried about their own job, or they just have a personality misfit with you, or maybe they're panicked about someone else judging them in their own career. There are a lot of very human reasons that bosses can be imperfect. Most bosses are imperfect. I was imperfect as a boss to people, and I've had imperfect bosses above me. But I think if you come to understand that everybody benefits from you having a healthy relationship with your boss, both you and your boss, then I think you can begin to try to work to make sure you have one, which is good for everybody and it's good for the company.

Adamek: So you mentioned imperfect bosses and I want to pose a couple of questions about the types of imperfect bosses that we see and how finance professionals can learn to take responsibility, to take ownership, for those relationships. And I want to start with a common complaint: the boss who doesn't give you credit or who steals the credit. How should someone deal with that kind of situation?

Dillon: Well, you first have to start by realizing there could be a lot of reasons that it's happening and not all are nefarious. It could be that the boss knows correctly that you are not yet ready for scrutiny by higher-ups, or you're not experienced enough to answer questions under stress, or whatever it might be, and the boss sees it as his role or her role to represent you and protect you but sort of you represent the department, and the boss is then representing the department in whatever the opportunity is. So it's not always for bad reasons. It can also be that the boss is very, very grateful to you but just in the moment sort of panics and worries about himself or herself being under scrutiny and inadvertently takes credit for something.

So there can be reasons that someone's very unintentionally doing it, not meaning to, and in no way meaning to disparage you, but it just ends up being how they act. There can be other reasons that are less healthy, where the boss is panicked about his or her own job and wants to make sure he or she looks good, where the boss is a micromanager and doesn't want anything to come out of his or her department or group without it looking like he vetted it, approved it, he was on top of the details, and usually, by the way, people who are micromanagers aren't really on top of the details. That's why they panic. They sort of have an intermittent need to know everything, maybe know too much, and then lose track of something, and they're not on top, so it's kind of a panicked response on their part.

It could be that the boss is just a jerk. It could be that the boss does want credit for everything and is not willing to see you grow, wants you to stay sublimated, you being the person whose job it is to make him or her look good, and then you have an unhealthy situation.

But the start is recognizing there's a whole arc of possible reasons, and they're not all bad reasons, and they're not all intentional.

Adamek: And how do you approach a boss in a situation like that?

Dillon: Well, you have to be careful, because you don't want to walk in with a chip on your shoulder saying, "You've taken credit for my ideas. I'm sick of this," or you don't want to at all undermine them or embarrass them in a public way in front of their superiors or their peers, your hand up in a meeting, "Well, when I wrote that memo —" that you didn't implied, or, "I don't think you understand that what I was intending ..." You can do things that make them look bad on the spot, which are not likely to be effective, in any case.

I think I would start by saying, if you actually have a good relationship with your boss, if your relationship with your boss is just entirely transactional, "Here's the report. Here's what you asked for. I got that done. I'll have it by Friday," you haven't built anything other than transactions out of it, and so to some extent, they will treat it like a commodity, the work product is a commodity that they expected from that transactional relationship.

On the other hand, if you find ways to get to know your boss as a human being, to understand what he or she is thinking about, caring about, going through at work, outside of work if possible, you build a relationship that has multiple dimensions and it's just always easier to be kind to, to be generous to, to be supportive of, people we like. It's just human nature.

So I would start by assessing, “Do you have a transactional relationship with your boss, or do you have a whole relationship with your boss?” If you don't have a whole relationship with your boss, then you need to work to build that.

Adamek: If it's a worst-case scenario and the boss is just a jerk, are there strategies for getting your work noticed throughout the company that aren't harmful for you?

Dillon: Yes. Again, always staying diplomatic and careful. I mean, I even think till the day you walk out the door, I would not bad mouth — till after you're out the door, I would not bad mouth the boss or appear in some way — unless it's important. Unless there's something really unethical or something going on. But if it's not, I think life is long. The road is long. You can look like just as much of a jerk being complaining about somebody that you work with.

I would take a high road, but I would look for opportunities to connect with other people in the company who might have some power and influence. They can be peers of your boss. They can be superiors of your boss. They can be people in other departments. Now, you're not looking to go over your boss' head. You're not looking to implicitly suggest that your boss is not competent, thus you're stepping up, but what you're looking for are ways that you could introduce yourself with, connect with, perhaps work on a different project with somebody in other parts of the company.

The more people at a higher level or in other parts of the company who know you, who know what you do, who know what you're capable of, who know your interests, the more likely you're not depending on a single point of failure, your boss, to either represent you, or to see opportunities for you, or allow other people to see opportunities for you. You broaden the prospect of you either finding other people who become your champion or opening up other job possibilities within the company for you.

Allowing only one person to kind of be the gatekeeper to you is a really big mistake. So slowly, subtlety find ways to connect with other people. It can even be as simple as at the company outing, talk to other people. Don't be isolated. Don't allow yourself to just sit with everyone who already knows you.

Connect with other people so that people begin to know you as a full person and not just the name on the report or the name not even on the report, the work product person. You're a person who has a lot to offer and a lot of dimensions of what you offer.

Adamek: So I want to take a slightly different tack. You have a boss that doesn't give you any credit, but then you might also have a boss who gives too much credit to someone or a boss who plays favorites. What's the first step in changing that relationship with a boss who plays favorites?

Dillon: The answer is, again, people are human and they do have favorites. They do tend to, and I've been the beneficiary of that sometimes in my career and I probably have also given other people that grace. You don't mean to. You don't think you do. You just tend to like somebody better or count on them a little bit more. The gravitational pull of working with, and delegating things, and having a favorite, can be very strong.

What I would say is — this is probably the biggest mistake I've made in my own career, I think — is you cannot let it get to you. You can't control, you're not gonna be able to stop the boss, or the manager, or other people from liking or admiring that person, and in fact, the more you think about complaining, or undermining, or showing that they're not really worth that extra attention, the more you will actually end up looking like the jerk, the problem person. So I think you have to be at peace with you may not be the favorite. There may be another favorite. That's just gonna happen. But what I would say is work to be a favorite yourself, not necessarily of your boss but just a colleague that people like working with, that people connect with. Maybe you're not the boss's pet, but you're everyone's pet. Everyone likes working with you. You're known to be. Rise up rather than try to take the other person down. I think that's the healthiest possible thing to do because it's very easy to fixate on how unfair it is but your boss or manager has somebody else that always gets the favorite stuff.

I remember at one workplace, my boss would take everybody to a Red Sox game, or people to a Red Sox game, and it was always this sort of nod, who was the favorite? Who's in, who's out. And I sort of waited for my opportunity to get asked to the Red Sox game, and you get obsessed about silly things like that. You know what? I did good work. I connected with my boss and with others well. That pays off far more in the long run than obsessing about the kind of ins and outs of who's the favorite.

Adamek: On the other side of that coin is a boss who treats the workplace like a competitive blood sport or pits employees against each other. When you're faced with that kind of situation as an employee, how do you take ownership?

Dillon: Again, some bosses do like that. I've seen actually bosses literally declare it, "I like a little healthy competition among the staff." I would, again, get a healthy attitude about it. Don't allow yourself to see yourself as competing with that person. You are trying to do work that shines. Your work should stand for itself. Your work should be better. Your work should be strong.

But it's not the other person who's the embodiment of all that you're fighting against. You're fighting against other companies, the competitors outside the company. Your energy should be spent on things that actually matter to the company, not having a kind of internecine battle.

So again, reframing it as, "I want my work to be strong," and that will speak for itself. "I want my work to be the winning work or the one that's most respected or admired." Start with that. Don't make it personal. And when the boss does make it personal, I think it's not unfair to ask for ground rules. "How will you decide? When will we know? What are my chances of getting X or Y thing?"

You don't want to be competing for something in a vacuum where you don't understand the rules and it feels like blood sport. It's not unreasonable to say, "I just want to make sure I understand how you're gonna make your decision about this or when we're going to work together again." Get some frame of reference from your manager because I think that's reasonable to ask for so that you can perform well but not see it as this endless rivals, that he's built up a rivalry within the company, which is not really good for everybody in the long run.

Adamek: As technology changes the workplace, how is that changing both office politics and interpersonal relationships within an office as people go more remote, as people are able to communicate in different ways with colleagues all around the world?

Dillon: Well, there are both pros and cons to that. Being remote and being able to work differently can mean, for some of us, lower stress. We don't always have to be fighting a commute. We can work how and when and where suits us in some way. And we can work collaboratively with different people than we might have seen in our office. And I think all that's great. It exposes other people, and us to other people, in new ways that can be fantastic. It allows us to work differently in a really positive way.

The negative thing about that is I just don't think much replaces human connection, the ability to chat with somebody at the water cooler, to laugh at something funny that happens outside the window that you can all see — a dog running down the street and the owner chasing him, or something. There's something about being together and feeling together, being part of something, that I think is really important, and we know, research tells us, that a lot of great collaboration happens from kind of incidental contact with people, for talking about something in the presence of someone else, learning about something at lunch that's interesting.

Those kinds of things don't happen when you're working remotely, so I think you have to either work to manufacture them in some way or look whenever possible to make sure that you do have some physical connections, check-ins, so that you don't become a team of people who are disconnected other than through email or any of the other forms of technology.

And the last thing I would say is I know it's very easy just to misread something when you can't see people's faces, misread the joke, or the intention, or something about what they meant to do, or when they didn't expect an answer, or you read an email too quickly and you misinterpret what it said completely. I think those things can never replace picking up the phone, talking to someone directly, solving a problem, before it stews three or four emails back, and/or looking someone in the eye and just saying, "I need you to explain that to me,” or "Why did you do that?"

The ability to talk to someone and get something out of it is so much stronger when it's in person, or, the minimum, on the phone.

Adamek: What are the skills that people need to develop to improve their ability to engage in office politics?

Dillon: I think really truly sort of practicing, and remembering, and understanding that most people don't come from a bad place. Most people are not trying to hold you back, or trip you up, or make you look bad. They're probably far more worried about making themselves look bad or themselves screwing up. So just understanding that what's behind an action that may be frustrating to you seldom has to do with you and certainly is seldom designed to injure you. It may be some cases where that's true, but I would start with allowing goodwill on people's parts, one.

And then, two is rather than letting it fester and stew, whatever is grieving you or making you annoyed, find healthy ways to ask about it, talk about it, speak one-on-one with people. Because it's so easy to take a little grain of sand of annoyance and somehow it gets built up to a pearl of an annoyance in the course of time, and you end up becoming the person that looks like the jerk rather than whatever it was that annoyed you in the first place.

And I know in my own career, when I've had the courage to ask somebody something directly or express myself directly, that, "It bothered me when you said X," or, "I don't understand why you didn't accept my idea Y," it's almost always been solved in a few minutes of conversation. Either I learned something important that I didn't know, or the person realized that they had been misunderstood. So I think having the courage to speak up for yourself diplomatically in the right circumstances and recognizing most people don't mean you harm is a really good start.

Adamek: Karen, thank you so much for joining us.

Dillon: You're welcome. It's been a pleasure.

Adamek: I'm Drew Adamek, senior editor with the Journal of Accountancy, and I've been talking with Karen Dillon, a former editor with the Harvard Business Review and author of the Harvard Business Review [Guide to Office Politics], about how to manage your relationship with a difficult boss. Thank you for listening and please check back regularly for more podcasts from the Journal of Accountancy.