Tricky Situation: Working With a Difficult Boss

Goal Setting in the New Year

ALL of us would like to work for a boss who sets clear expectations, is supportive, and wants us to succeed. In the beginning of a new relationship, they may show signs of being that type of manager or supervisor. However, what if things change over time or they become more challenging and difficult as the relationship matures? What can you do? What do you do?

Successfully managing the relationship with your boss requires you have a firm understanding of both your boss and yourself, particularly strengths, weaknesses, work styles, and needs. Learning to better “manage the relationship” with your boss is not about political maneuvering or brown-nosing; it’s about the process of consciously working with your boss to obtain the best possible results for you, for them, and for the company. Most importantly, it’s making sure that your boss knows that you are committed to being in alignment with the things that are important to them.

So, how do you do that in a way that also feels good to you?  Here’s an example of a recent coaching engagement where this issue arose:

Shelia was a very talented media executive who had risen through the ranks by being good at her job, working hard, and delivering a great product. When her engagement began, Sheila admitted that she had never thought managing her boss was a part of her job. She had never been forced to manage a relationship with a difficult boss and was a little shocked that she was being asked to “find a way” to do so, now.

In this case, it wasn’t a matter of merely a personality conflict. It was a misalignment of expectations. Her boss believed that he was being measured by “being in the know” about everything that was going on in the work environment. Sheila believed that she was expected to lead the team with little involvement from her boss. Her boss was being called on continuously to deal with complaints related to Shelia’s unreasonable and unrealistically high expectations. Shelia’s boss wasn’t aware of any performance issues among her team because she didn’t think he needed to know.

In this case, Shelia needed to sit down with her boss to better understand what the issue was and why it was important to him. Shelia needed to agree to modify how she communicated her high expectations in a way that was more palatable for her team and avoid the need to be so self-sufficient. It was a matter of being more open to sharing critical information that would bring her into closer alignment with her boss’s expectations.

So, in this case, it wasn’t Sheila’s boss being difficult to work with, but being out of alignment on their expectations of working together. Sheila and her boss were able to agree on a set weekly touch base where both of them could share information about what was going on, as well as set some clear and mutual expectations going forward, to better meet both their needs.

If you find yourself in a similar situation or just believe you and your boss are having difficulty communicating, here are some things that might help:

  • First, make certain that you are delivering good work in your role!
  • Then, fully understand what your boss’s goals are and how you can help him achieve them; how is they are being measured?
  • Seek to contribute more than just getting ahead
  • Pick the battles that really matter and make a case for why they matter
  • Build relationships with other key executives in the organization (this can be helpful in building advocacy for your work)

And, if your boss is really difficult to work with, be willing to act and tell someone that has the ability to change the situation.

Look for more ways to handle “Tricky Situations” in future blogs about this topic. And, to learn more, email Patty at pprosser@cciindy,com or call 317-727-6464.

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