Wright Foundation | December 2, 2021

How to Deal with a Difficult Boss

Dealing with a difficult boss isn’t always easy, but there are steps you can take to empower yourself.

Learn how to deal with a difficult boss without worrying about making work uncomfortable. You can take charge of your career.


I hate my team leader!

My boss is a jerk!

I cannot deal with my supervisor—she’s the worst!

If you’ve been in the workforce for even a few years, chances are you’ve had a run-in with a tough boss, frustrating supervisor, or manager who makes your blood boil. Knowing how to deal with a difficult boss is one of those work skills that’s not taught in college (but is all too necessary).

The thing about dealing with a difficult boss—or a tough boss—is that sometimes it’s not just them. I hear the comment, “my boss is a jerk,” a lot, and yes, in some cases, your boss might actually be terrible. Some abuse their authority and power position. But in almost every situation, there are steps that subordinates can take to empower themselves and address the problem.

So, here’s how to deal with a difficult boss (before you decide to quit).

“It’s Not You. It’s Me.”

I’ve heard many people say they think their boss is a jerk. My answer to them is, “has it ever occurred to you that you may have authority issues?”

Now, most people don’t like to hear that. I admit it may sound harsh at first. But it’s up to each of us to deal with our situation, build rapport, and find ways to improve our situation. Otherwise, we’ll see that the “bad boss” mentality follows us throughout our careers. One bad boss may be a fluke, but a string of bad bosses? It’s probably time to look internally at our reaction to power and authority.

I’ve worked with clients who have had some of the toughest, most challenging bosses on the planet. So the first order of business is always getting them to operate in good faith with their boss as we would in a relationship—assume goodwill. Assume that a boss wants their team to perform and to do a good job.

I will add the caveat that if a boss is truly a jerk—abusive or demeaning, then we should address those cases with human resources immediately.

When we face a truly intolerable situation with someone who tears us apart, it may be time to liberate ourselves from the job and find other employment that’s a better fit. It’s within our power to refuse to be mistreated by a boss (or anyone else). We do not need to be a victim of someone else’s bad behavior.

But in most cases, we may need to look at our behavior and our reactions to the challenges put forth by our boss. For example, if we feel our boss is pushing too hard, raising expectations higher, or offering more challenges, could it be that they actually believe we’re capable and competent?

Is it that we don’t want to give the situation our best effort? Are we offering 100% for the time that we’re paid? Are we working our best and working in good faith—doing our jobs with the intention to succeed and empowering others on our team to achieve as well?

Often, when we take a step back from the frustration of the situation, we may realize we’re not pushing ourselves as much as we could. If we’re operating in “bad faith,” we may believe that our position or territory matters more than the success of our coworkers (or even the company). We may be more interested in passing up our peers than lifting up our peers. We might not be helping others reach their potential.

The truth is that many people seek a job where they can phone it in. They want a position where they walk in, punch a card, and do a mediocre job. But an easy job is a recipe for a job that they hate. When we pick an easy job, we will often resent a boss who calls us out on a lack of motivation. We will resent coworkers who care about their positions and work for the well-being and success of the company.

However, when we shift our mentality and decide to engage, speak up, and buy in, we can completely change our perspective about both our job and our boss. When we start seeing the company’s success as our success, we take ownership. We push ourselves further, seek new assignments and new opportunities. We zone in instead of zoning out.

When we aren’t working for what’s best for the company and what’s best for our boss, then we aren’t operating from a trustworthy position—we’re letting our problems with authority get the better of us. So when we point the finger at our “jerk boss,” it may help to remember that three fingers are pointing back at us.

Deal with a Difficult Boss by Dealing with Unfinished Business

When it comes to working, our relationships often mirror the relationships we have outside the office. Our connection with our boss may mimic the relationship we once had with our parents. After all, the boss offers us resources (money), direction, and (sometimes) praise. In many ways, it’s similar to a parental relationship.

How do we address these issues and frustrations we might have with our parents? Again, it comes back to what’s called “unfinished business.”

Like it or not, each of us carries around limiting beliefs about ourselves that stem from our early childhood. These beliefs include the idea that we’re too much, that we’re not enough, that the world is dangerous, or that we can’t get what we need.

Today as an adult, we probably think we don’t carry these beliefs anymore. Logically, we know that we’re grown up, but our limiting beliefs are often still there under the surface. These beliefs may dictate what we do, our perception of the world around us, and our relationships with others and ourselves.

For some of us, our parents may not have had our best interests at heart. Maybe they had their own interests instead. Or perhaps a parent was abusive or hurtful. We may have had a parent that made excuses for another parent’s bad behavior, defending them with excuses like, “He does this because he cares about you,” or, “She acts that way because she loves you.”

These messages stick with us throughout our lives and cause us to fall into familiar patterns, especially in our work dynamics. We may find our relationship with a coworker is similar to a sibling, or a supervisor reminds us of our parent.

We may fall into patterns depending on our relationships growing up, including what doctor and author Stephen Karpman called the “Drama Triangle.” The triangle consists of three roles: Rescuer, Victim, and Persecutor. We may fall into the role of victim when our boss acts as a persecutor. Or we may rush to rescue a coworker when a manager offers harsh feedback. We may even trade off the different roles, depending on the situation. For example, when given authority, our inner persecutor may come out.

As humans, we’re all drawn to drama. Look at our love of reality television and dramatic movies. We get sucked into the classic storyline of villain, savior, and unfortunate, hapless victim. But truthfully, the drama triangle is an unhealthy zone. It’s disempowering for all participants. It robs us of our ability to stay in control of ourselves and the situation. The drama triangle masks as engagement, but it’s pseudo-engagement. We’re stirring a pot, but it’s not going anywhere.

As we reflect on this, some of us may think, “I had a perfect childhood! I never had any drama.” It’s common for people to assume that they must not have limiting beliefs if they had a great childhood. But by the very nature of childhood, all of us experience limiting beliefs. The world is big, and we’re small. The world is unsafe, and we look to our parents to guide and protect us.

As we grow, the world is no longer too big for us—we can reach the pedals and read the signs. We’re now operating in a world made for adults our size, but we still carry around those limiting beliefs and unfinished business. It’s up to us to work through our business, or it will continue to crop up in our relationships in our personal life AND at the office.

So if our boss is a jerk, we can ask ourselves, how are we allowing them to be a jerk? Are we falling into the drama triangle, hoping someone will intervene and rescue us? Do we fall into a role because it feels safe to let someone else fight our battles?

Standing Up to Jerks

A client came to see me. He was a C-level officer of a major global company. He was in charge of many people and doing well professionally, but he had the same complaint that so many have: “My boss is a jerk.”

So he and I started to break down the situation. We examined his unfinished business and what he could do to address it. He worked hard to build the courage to stand up to his boss. Finally, one day he did it. He called him out in a very public situation—a stakeholder meeting. He did it abruptly and angrily and ended up humiliating his boss.

In some ways, the confrontation was a significant success in addressing his authority issues. But, unfortunately, now he had a more substantial problem—he’d lost any chance of good faith and rapport with his boss. So he and I began to work on ways he could address the issue. I started coaching him on how to win his boss over.

It all clicked when he realized he needed to give work his all. He needed to push himself to take on more challenges. But, more importantly, he needed to be straightforward with his boss. He needed to build back the trust with unwavering honesty.

Fast forward a few months, and he became his boss’s closest confidant throughout most of his career. Then, one day a close friend of his boss walked up to him and said, “Once this guy has an opinion, he NEVER changes it. I’m blown away by how you went from a person he didn’t trust to becoming his closest advisor.”

The client had been reacting to his boss due to his own unfinished business with his family. As he worked through the business, he stopped projecting it onto other people and situations. He was able to move to a place of good faith with his boss. He stopped using his boss’s behavior—even bad behavior—as an excuse for his own bad behavior.

When the company faced changes, he was the most valued person in the transition. As a result, the company went through a very successful change and growth, thanks to my client’s work with his boss.

When we’re dealing with a difficult boss, we need to look at our behavior and reactions. Are we falling into old patterns? Are we jumping into the drama triangle?

It’s always possible to turn around our relationship with our boss and start working toward a place of mutual good faith. We need to find ways to challenge ourselves and push ourselves past our comfort zone. We need to express our feelings honestly to our boss—even if we don’t like something. We should learn to speak up rather than shy away from confrontation. When we come from a place of honesty and authenticity, we will start to move toward the career we want.

For more ways to boost your career and build better connections, please visit Wright Now. We offer an array of courses to help you get more from your work, relationships, and yourself. Start getting more of what you want now!


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The Wright Foundation for the Realization of Human Potential is a leadership institute located in Chicago, Illinois. Wright Living performative learning programs are integrated into the curriculum at Wright Graduate University.