How I Dealt With A Boss From Hell

In January of last year, I took a job that taught me a lot about interpersonal relationships, office politics, and how to deal with an alcoholic for a boss.

Within the first week at this company, my boss was already bad-mouthing employees in front of me, asking me (at noon) if I wanted to join him for a shot of whiskey, and speaking disparaging things about women, arabs, and black people in casual conversation (he believes racial/ethnic slurs are only politically incorrect). Within a couple of months, he was bad-mouthing me to the CEO’s daughter, inviting my interns to the bar after work, and aggressively endorsing Trump at company events. I’d had other bosses before so I knew what it meant to be professional. This guy was a real piece of work.

Luckily, this person was only the boss I directly reported to, so there was a hierarchy above him that I could approach concerning his behavior. Here are some tips on how to deal with a boss like this.

  1. Take them to lunch. Why would you want to take someone like this out to lunch? If they’re behaving this way, it could just be that there’s something going on in their personal lives. Try to create a respectful work relationship (since they couldn’t) and show them that you’re on their side. This may not work but it’s worth a try.
  2. Keep record. If your boss tells you to change something on an assignment or do something other than what you should be working on, ask them to send you an email request. If they deny the email request, notify your boss, your team, and relevant higher ups via email that you’ll momentarily be working on a different assignment or changing the project at hand. If your boss’s decision ends up being questioned by their boss, they won’t be able to blame it on you (I learned this the hard way).
  3. Set boundaries. If they start talking about subjects that are unprofessional or make you uncomfortable, politely redirect the conversation. If they continue circling back to these topics, tell them you don’t like discussing those topics at work.
  4. Don’t drink with them. It took me a month to figure out my boss was an alcoholic. Before this, I’d joined him and the team out for drinks after work a few times to get to know them. While it’s definitely okay to grab drinks with coworkers every once in a while, my boss did this at least twice a week in addition to his showing up to work hungover and drinking on the job. If you notice that your boss is a alcoholic, don’t participate in drinking behaviors with them. If they ask you to go for drinks, ask them for coffee or tea instead.
  5. Address the problem. Chances are, the both of you know there’s tension between you. Schedule a meeting with your boss and HR to talk about it. If things don’t improve or if they worsen (as it worsened in my case), schedule a meeting with your boss’s boss (or a relevant authority to whom you both report to/hold meetings with). Do not invite the boss who is giving you trouble to this meeting. I had this meeting with my boss’s boss (he was always in our team meetings and we already had a professional and friendly relationship). While the meeting didn’t help to improve my direct boss’s behavior, it did change who my direct boss was. I no longer had to report to the disrespectful boss because his boss changed the office hierarchy so that we both had to report to him.

As you can imagine, this change really bothered my now former boss. He became more erratic and drank even more. The situation at the company wasn’t really changing so I began looking for a job that allowed me to work remotely until I started medical/law school (I had taken this managing position after graduating university and was using it to fill time while I decided between medical school and law school). I’ll be starting law school in the fall and am very grateful for the time I spent at that company. I learned a lot about how to deal with people (terrible bosses in particular) and I know that it will be invaluable to me in the future.

13 thoughts on “How I Dealt With A Boss From Hell

  1. Good advice. Very useful things for people to know. It’s good that there was a hierarchy above him–and that they were willing to listen. Too often, I’ve seen problems like this compounded because upper management doesn’t care.

    Liked by 1 person

  2. You are so wise at such a young age. You will make a terrific lawyer, no matter what area of law you go into. Of course what your boss was doing could have been reported to the Dept of Labor as creating a hostile workplace. The entire company would have paid the price. I am glad you were able to work it out with them.

    Like

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