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4 Steps to Help You Deal with a Difficult Boss

4 Steps to Help You Deal with a Difficult Boss

July 12, 2022
Lead Self
Joseph Cook

Throughout the last several years leading team and leadership development programs at WinShape Teams, one of the most common obstacles for leaders and team members when returning back to work is dealing with a difficult boss. Participants frequently come to our programs, become inspired, and are reminded of simple practices that lead to more effective results, but then the dark cloud of who they report to diminishes their hope for a preferred future. 

While dealing with a difficult boss is, unfortunately, extremely common, what makes each boss difficult to work with may be unique to each person’s particular setting. With that being understood, it will be impossible to provide a clear answer for how to handle every situation involving challenging leaders; instead, the purpose of this article is to share some general tips for where to start when dealing with a difficult boss.

4 Steps to Help You Deal with a Difficult Boss

Four Steps to Help When Dealing with a Difficult Boss

Here are four simple steps that can create some clarity as you lead yourself through this challenging obstacle. It is important to remember that these steps work best when they are used together. Following through with the first step and halting without moving forward will prevent lasting change from occurring; it could possibly also do more harm than good, so try to ensure each step is given the attention needed for progress. 

Step 1: Define the Difficulty 

During my years in the fire department, I was blessed to have had many servant leaders as captains, but there were also some difficult “bosses.” One example is when a supervisor would take over and do everything himself rather than coaching the younger firefighters to be more effective. This may be appropriate when stakes are high and the lives of citizens are on the line, but this would occur in low-risk and even training environments. It was hard to grow when the opportunity to do so consistently got taken away. This boss was overly controlling and a severe micro-manager. 

I am sure you have experienced an example like this and many others, but the first step in dealing with a difficult boss, regardless of the situation, is to define what is specifically difficult about your boss. Avoid the temptation to say, “Everything!” Spend some time and dig in deep to reflect on what it is that makes following this person difficult. Are they a micro-manager, unavailable, close-minded, etc.?

Defining what is difficult about your boss does not make them easier to work with, but it does set a good foundation for moving forward. It is also important to be respectful during this process, so be careful to avoid gossip and slander; this step is a personal reflection exercise.

We are not defining the problem so we can tell them off more accurately. It is purely for the purpose of working towards a solution.

4 Steps to Help You Deal with a Difficult Boss

Step 2: Lead Yourself 

After defining what is specifically difficult, the second step in dealing with a difficult boss is to lead yourself to make any necessary adjustments. Julian Rotter, a psychologist who specialized in social learning theory, authored the concept of locus of control. He explained that a person with an external locus of control believes they have little to no control over what happens to them, and a person with an internal locus of control believes they do have the ability to influence outcomes.  

It can be natural to claim that your boss is too controlling, close-minded, or unavailable and convince yourself that there is nothing you can do to control them. You would also be right; you cannot control anyone, but you do have the ability to influence the outcome for them and for you. It is easier to control yourself than others, so start with making your own adjustments rather than waiting on others. 

In graduate school, my professors had different personalities and expectations, and do you know what I did? I just wrote papers the same way, no matter what, hoping they would lead to an “A.” No, that would not have been productive. I spent the start of each class paying close attention to what my new professor expected and changed my style accordingly to meet their expectations. 

I am not asking you to change who you are or your core values and beliefs. I am referring to a two-degree shift; micro-adjustments that could have a big impact on how you interact with your boss.  Try to demonstrate the change you want to see in others. Making adjustments on your end could make the most immediate impact. 

Step 3: Seek Understanding 

When others behave in a way that conflicts with our beliefs, values, or expectations, a natural reaction is to jump to judgment and create a narrative in our head about the other person. After defining what is specifically difficult about your boss and making any micro-adjustments on your end, the next step is to seek understanding 

In the fire department, the captain of a company would own the role of making a 360-degree assessment as soon as we arrived at the scene of an emergency. This would involve walking completely around the perimeter of a structure to quickly inspect the scene. This assessment is a critical step because the captain needs as much information and context as possible in order to direct our team with how to appropriately respond.  

The reason I bring up this example is because, as a firefighter, I knew that the captain was able to see things I could not see from my vantage point. In the moment, I followed the command without hesitating; later at the fire station, I would ask questions about what the captain saw or heard that influenced his or her decisions. This deeper understanding helped me grow as a firefighter by clarifying expectations for future emergencies and what to expect from my boss in those settings. 

Abraham Lincoln once said, “I do not like that man; I must get to know him better.” I love the simplicity of this statement but also how profound of an idea it is in our world today. Lincoln held the belief that getting to know others better with a deeper understanding provided a way to ease tension.

Instead of avoiding interactions with your difficult boss, try leaning in a little more to build a stronger relational connection and clarify expectations for your role. 

4 Steps to Help You Deal with a Difficult Boss

Step 4: Make a Decision 

Even if you follow the steps above, your boss may still be difficult. This may be an acknowledged, explicit misalignment of values, low competence, or a complete lack of self-awareness, and positive change may not be on the horizon.  Your next step may be as simple as a two-way fork in the road.  

The final step is for you to ultimately make a decision. Do you continue to follow this leader, or do you decide to jump on a different bus? The good news is that this decision is yours 

While that sounds overly simplistic, I know there are several factors that influence this decision. It may not be so easy for you to willingly leave a job when providing for your family is on the line and the opportunity of another job is not guaranteed. This is understandable, but YOU are still making the decision. You are deciding to stay with your current boss, and that may be the right decision for you.  

It may be time for you to “fire your boss” by choosing to leave your current environment to find another job, and this may also be the right decision. It is understandable that bosses sometimes have to fire people when values and expectations are misaligned, but you have the same power. Employees can fire their bosses by saying, “I am choosing to no longer follow you.” 

If you choose to stay with your current difficult boss, again, that is okay. Just do not give up trying to apply steps 1-3 over and over again until it helps or until there is a better opportunity to leave. If you choose to leave, that is okay, but pay attention to what you learned through the process. Your experience dealing with a difficult boss may help you discern what to look for in your next boss.

To the Bosses 

Many who are reading this may be picturing their current bosses or bosses they have had in the past; however, have you paused to consider if you could be a difficult boss? While this article is not targeted at bosses, it may be helpful in your growth to think about this question: If you had to follow you, would you want to?

4 Steps to Help You Deal with a Difficult Boss

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