5 Ways to Work With a Difficult Boss

I got a call last week from an old friend. After we exchanged some pleasantries about our families, the reason for his call came quickly.

“Hey Scott, I have been reading your leadership blog for several years now and I was wondering if I could ask you a question. We just did a reorganization at work and I got a new boss. I connected well with my previous supervisor but this new one is off to a rocky start. Wondering if you have any tips?”

After asking if my friend had experienced rough starts with other supervisors in the past, and getting a “not really” response, I started thinking about how it feels to work with difficult people.  

The first thing that clients I have had in the past want me to focus on is changing the other person, in this case, my old friend’s boss. Since I am not working with the old friend’s new boss, the odds of me invoking any kind of advice to change that person is slim to none. 

What we can work on, however, is how my old friend is responding to his new boss. Here are the things we talked about that day:

5 Ways to Work With a Difficult Boss

  1. Maintain Long-term Focus: It is so easy for us to get caught up in the emotion of the moment. All of the frustration and anxiety that can come from a new relationship can seem paralyzing. Keep in mind that the supervisor you had prior to this one took time for the relationship to develop. Even if it started off on a good foot, relationships take time to evolve. So if this relationship gets off to a rocky start make sure to keep a long-term perspective. When I asked how long my friend had worked for the previous manager he said about 2 years, which is about how long he has worked for anyone over the last 20 years at the company. Supervisors tend to be temporary, and very few work relationships last forever. 

  2. Find and Convey the Good: When we have irregular people in our lives (those that are hard for us to connect with), it is really easy for us to focus on all the negative things. Focusing on the negative does one thing, it forces us to only look at all the bad. A simple recognition of what is not going so well is ok and something to process with a coach or trusted advisor. But dwelling on what is negative is not helpful in the long run. So make a list of all the positive things the new boss is bringing to the table and do the best you can to focus on those. 

  3. Have a Spirit of Acceptance. There are many reasons that a relationship with a boss might get off to a rocky start. Very rarely, the reason is that the boss is innately evil. While I always want to give space in a relationship for moral hazard, most of the time the new boss just wants to win, maybe they have been told to shake things up, or they have strong preferences based on their past experiences. Whatever the reason is for how the new boss is behaving, as long as it is not immoral or illegal, you can try to approach them with a spirit of accepting them for who they are…warts and all. I try to keep in mind that the new boss is checking me out as well and I might have a few warts myself.  Sometimes all a boss needs from us is to connect with them without judgment.

  4. Set some clear boundaries for yourself. It is very true that you might not be able to control or change the other person but you can always control your own actions. According to John Townsend in his book The Hiding Dilemma, “People with healthy boundaries can say yes to the good and no to the bad.” The person who is saying yes to someone else’s demands out of fear is setting themselves up for failure. Plan what you can say yes to and what crosses the line in your mind that you must say no.  Resist the temptation to just say yes to try and please them or get on their good side. As you plan your boundaries, keep in mind what you are willing to do in certain situations and what you are not willing to do.

  5. Stay Open and Curious. If a relationship is tense from the start, our natural inclination is to protect ourselves and fight. None of us wants to get hurt in a relationship or get sideways with a boss especially if we really enjoy our work. According to Edgar Schein, if you practice “Humble Inquiry” you will stimulate more truth-telling and collaboration.  By staying humble in your own character and curious about what might be going on you can stay out of judgment and see more clearly what the boss is all about.

Your Development

From time to time we are all going to work with people, who are for whatever reason, tough for us to process. Here is a case study for you to write about yourself to help you see how you might strive to improve the relationship. Remember you are the one sensing the tension. You are the one who may have to flex and find a new approach.

  • Think about a conversation or situation with a boss that went very well.

  • Now think about a situation or conversation with a boss that did not go well.

  • Compare your Thinking, Feelings, and Behavior in each circumstance. Use the chart below to guide your thoughts:

As you study the chart above, what are you learning about yourself and your approach to working with people who are more difficult for you to relate to?