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Dealing with a Difficult Boss

| November 9, 2021

by Jim Bruce

[Jim Bruce is a Senior Fellow and Executive Coach at MOR Associates.  He previously was Professor of Electrical Engineering, and Vice President for Information Systems and CIO at the Massachusetts Institute of Technology, Cambridge, MA.]
It is wonderful to have a good boss, one who is understanding, supportive, provides challenging assignments, shows an interest in you and your work, etc. You get the picture. I have had two such excellent bosses in my career. They were great and were real partners with me in getting the work done. However, that is not always the case.

Most of us will encounter a difficult boss or two or perhaps more in our careers. I had two in my some 40 years at MIT. One never seemed to follow through on his important commitments and the other always had the “right” approach or answer which too often wasn’t. Also, on my list are two additional individuals who often fell asleep during one-on-ones. One of these fell asleep while I was interviewing him as a candidate to be my boss. (When I told the individual, who would become this person’s boss about the candidate’s falling asleep, he responded that he had that problem too. I already knew that as he had fallen asleep in previous meetings with me.)
There are a number of lists in the literature (see here, here, and here) of traits that bad bosses exhibit. These include:

  • Bosses who take credit for your work and that of your team.
  • Bosses that don’t empower those who work under their direction.
  • Bosses who don’t support you in front of your team and your clients.
  • Bosses who don’t care if you are overloaded or have impossible deadlines.
  • Bosses who never give you exciting or challenging assignments.
  • Bosses who don’t set clear expectations.
  • Bosses who avoid conflict, sweeping problems under the “rug,” etc.
  • Bosses who know “everything.”
  • Bosses who are micro-managers.
  • Bosses who have poor listening skills.
  • Bosses who only care about themselves.
  • Bosses who say it’s my way or the highway.
  • Bosses whose singular focus when there is a problem is to ensure that the blame is focused on someone else.
  • Bosses who don’t respect the staff.
  • Bosses who are not self-aware.

In spite of this list’s length, it is not exhaustive. I’m sure that you have other examples to add from your own experience.
I see two big take-aways here: First, it is very likely that there is no way you can escape working, at one or more points in your career, for a difficult manager who exhibits some of these characteristics. And second, when this happens, you need to feel compelled to ask yourself “what do I do” and get an answer to your question, and not just ignore what’s happening or run for the door.
Though we are very likely to think of our bosses as being good or bad, Mary Abbajay1, president and co-founder of Careerstone Group, LLC, a woman-owned, full service organizational and leadership development consultancy, suggests that it is not helpful to think of bosses and managers in that way. Rather, as career coach Sarah DiGuilio2 suggests, you should think about your manager in terms of three qualities – is he or she organized, does he or she help get things back on track, and does he or she deliver on the goals of the organization.
DiGuilio also notes that an effective manager supports the people they are managing, values these people, listens to them, coaches them, and cares about their engagement and their well-being. She also notes that managers listen, are honest, trustworthy, and hold those who work with them accountable and provide support where needed.
So, what do you do when your manager is not effective?  There are three general answers to this question: You can complain to your manager’s manager, you can find another position at your present (or another) employer, or you can work to make your current situation better.  In the remainder of this essay our focus will be on the latter, making your current situation better.
What specific things can you do to be more effective working for your difficult boss. Here is a list of six things that you may find helpful:

  1. Start by taking care of yourself. This begins by clearly defining and holding fast to your principles. Those define who you are. At a minimum, get enough exercise, spend time with you family and friends, and get enough rest each night.
  2. Understand your boss as much as you can. Don’t make assumptions about what he wants or doesn’t want, ask. Don’t make hints about what you want or need. Be direct, ask. And, just because your boss says that he or she will deliver on your request, they sometimes, perhaps even often, won’t. You will have to rely on your judgment as to whether, and how, to ask again. Not delivering may be your boss’ way of saying no.
  3. Carry out your assignments. Your excellent work is your best “weapon.” Take pride in the professionalism and quality of your work. Your good, timely, work and the professionalism through which it is done make you, your boss and your group look good to your clients. This is valuable.
  4. Add value.  Lead by example, show up with integrity, be professional, don’t let your difficulty with your boss impact your work or your relationships with your clients of others. 
  5. Make specific requests. Difficult bosses often don’t take feedback well, often don’t handle assumptions you may make about him or her and what he or she wants or would be okay. So, ask. For example, rather than assume you can ask a colleague on another team for help, it would likely be better to go ahead and ask your boss. 
  6. Deliver on your commitments, both large and small. If you cannot, don’t assume that your manager won’t notice or, that it will be okay. Be up front as far in advance as possible. Explore options that you have considered with your manager, ask for advice.

Working for a difficult boss is a challenge. It can be nerve-wracking, it may make you want to scream and cry. It can also be a time when you really grow. And, it may be a time when you decide you have to go and there is no shame in that.
If you are now working for a difficult boss, I trust that you will find this essay helpful. I wish you every success as you continue your journey, whether you stay or move to your next opportunity.
Do all you can to make it a good week for you, your team, and your manager.
.  .  .  .  jim

  1. Mary Abbajay, What to Do When You Have a Bad Boss, Harvard Business Review, September 2018.
  2. Sarah DiGuilio, How to deal with a bad boss, NBC News, March 2020.

Other Reading:

  1. Mary Abbajay, Managing Up: How to Move Up, Win at Work, and Succeed with Any Type of Boss. John Wiley & Sons, April 2018.
  2. Forbes Young Entrepreneur Council, 12 Traits Bad Bosses Have in Common, Forbes, September 2018.
  3. Jared Shelly, Managing Up: 10 Ways to Deal with a Bad Boss, Catalyst by Convene, undated.
  4. Ron Carucci and David Lancefield, Every Leader Has Flaws. Don’t Let Yours Derail Your Strategy, Harvard Business Review, September 2021
  5. Jim Clemmer, Bad Boss: Learn How to Manage Your Manager, The Clemmer Group, undated.