How To Tell If You Are In A Dysfunctional Relationship With Your Boss

If you feel like you’re just trying to please your boss rather than do your best work, you might be in a dysfunctional relationship. Here’s how to tell.

How To Tell If You Are In A Dysfunctional Relationship With Your Boss
[Image via Unsplash | Justin Leibow]

Like many realizations, Jennifer Winter had an epiphany as she was crying into her beer. It was at one fateful happy hour, she recalls, that something dark dawned on her: she was in a dysfunctional working relationship with her boss–and she needed to get out.


As she shares her story at the Daily Muse:

After growing up as a pretty normal, happy kid, the term “dysfunctional” seemed more Jerry Springer than Bob from accounting, but there I was, crying over my beer at happy hour, venting about my horrible boss and how I felt like I could never measure up to his expectations. It was at that moment that my drinking buddy stopped me to clarify: “Wait, are you talking about your family–or your boss?” Oof.

Having that indistinguishability between familial and professional relationships might sound strange, especially if you put stock in the phrase “it’s not personal, it’s business.” But sociologists and organizational psychologists have found that while one kind happens at home and the other happens in the office, work and personal relationships are both fundamentally relationships.

Which means that the relationship you have with you boss can have negative patterns of behavior, just like personal ones. So let’s suss out what that might be like.

Unsavory boss relationships can come in a variety of flavors.

Sometimes the bad work relationship stems from the higher-ups behavior, like if you have to deal with a micromanager, a yeller, or a neglector. Each of those can be addressed in kind.

But from what Winter says, a toxic employer-employee dynamic can also come as a two-way street. Like, she says, in the case of the rebel dynamic, where you and your boss are constantly challenging one another on every point. Or the sufferer dynamic, where there’s some expletive-fetching power dynamics at play–like, for instance, if your boss is dispatching you to get her dry cleaning. But the most difficult to catch, we think, is one that’s also terrible for building your career or making ideas happen–that of the perpetual people pleaser.

Keeping your boss contented with your work is a good thing. But making all your work about keeping him or her content is not a good thing. Winter describes the situation she got herself into:


… when (my boss) was pleased with my work, my quality of life in the office improved exponentially. For example, if I handled a situation well–usually one he didn’t want to deal with himself–he’d make a big show of it in the office or take me out to lunch or a drink. And when I didn’t meet his expectations, all hell broke loose. I quickly learned that making him happy was the only way I could make it through the week.

The problem with this was that I wasn’t focusing on how to innovate or improve my role or my skills, but rather what mood my boss was in that particular day and how I could get on his good side.

Why is this a problem?

1. You career stalls.
Because Winter was preoccupied with “keeping the dragon in his lair” rather than evolving her career: the careful work of making measurable changes, training in-demand skills, and forming bonds within the organization.

2. Your company suffers.
If Winter was spending all her time keeping up office harmony, she wouldn’t be able to do the experimental work that the best companies prize–and thus the whole organization would get into innovation debt.

What to do about it

Winter’s situation got so dysfunctional that she had no choice but to leave. But if the situation can still be salvaged, it might be time to give your boss some thoroughly constructive feedback.

Hat tip: the Daily Muse


About the author

Drake Baer was a contributing writer at Fast Company, where he covered work culture. He's the co-author of Everything Connects, a book about how intrapersonal, interpersonal, and organizational psychology shape innovation.