Ten Things: My Boss is a [Censored] – What Do I Do?!

One of the most frequent questions I get from in-house lawyers is how to deal with difficult bosses. I have been very fortunate because – while practicing law for almost 30 years – I can count on a couple of fingers the times I was stuck with a boss who was a real asshole.   After talking with a lot of other lawyers (at firms and in-house) I realize how lucky I have been in my career.  While rare, I definitely remember how miserable I was the few times I did draw the short straw.  Practicing law is tough enough without having to dread coming into the office because of a boss that just makes your life miserable.  Still, I survived and got through it.  But it wasn’t always easy and some days it really took a toll.  I think my revenge was getting to the General Counsel chair a few times and swearing a blood oath to myself that I would never, ever be a jerk boss – something I remind myself of every day.  Unfortunately, the problem of crummy bosses in legal departments will never go away.  They are out there and they always will be.  So, if you want to be a successful in-house lawyer you’re going to need to learn how to deal with them whether they are legal department lawyers or executives in the company (lawyers have no monopoly on being buttheads).  This edition of “Ten Things” will set out some of my tips on how to deal with troublesome bosses:

1.   Are they really an asshole or just a hard-ass?  Yes, there is a difference.  A hard-ass is someone who sets high-standards, expects you to get your work done on time and done well, calls you out when you mess up, tells you that t-shirt and sandals are not appropriate work footwear, and probably isn’t going to approve your vacation time in the middle of an acquisition you’re working on.  They are tough, but consistent and fair.  There is nothing wrong with any of this.  I have no problem working for a hard-ass, and neither should you. In fact, you should appreciate it.  An asshole, on the other hand, lies, is disrespectful, yells, blames others for their mistakes, takes credit for others’ work, sets ridiculous arbitrary deadlines, and puts themselves before their team.  They are tough, but inconsistent and unfair.  Working for a jerk like this is always a problem and there is nothing to appreciate about this problem.

2.  Is it you?   If you think your boss really is a jerk, you need to ask one more question: is it you?  First, jerk or not, your boss likely had to get something right to get to the position they are in.  Promotions to management are usually not handed out to incompetents, so, they are probably not a total idiot.  Do others in the department or company see them the same way you do?  If not, do some more thinking here.  Are you doing the things needed to be a successful in-house lawyer or are you just mailing it in? Are you the last one in and the first one out?  Do you ever volunteer for projects?  Can you be counted on at crunch-time? Do you shut down at 5:00 pm and don’t check emails until you get to the office the next morning (or not at all over the weekend)?  Do you spend a lot of time playing on the Internet while at work?  If any of these things describe you, you may be the one in need of an attitude adjustment and not your boss.  Being an in-house lawyer is not easy, and it certainly is not a “9-5” job.  And if you don’t want to work this hard, you may have made the wrong choice of career or at least the wrong legal department.

3.  Ask others for help.   If you have gotten through the first two questions and still think your boss is the problem, then you need to start taking some proactive steps to stop the abuse and preserve your sanity.  The first thing to do is to ask others in the department (or those who are peers in the company) for their advice.  Anyone else who works for – or knows – your boss should be able to help you figure how best to deal with him or her since it’s highly unlikely you are the only victim (and if you are the only one, see No. 2 above).  Your colleagues may have developed coping mechanisms or other ways to deal with the boss’ outlandish behaviors that you can adopt too.  Plus, sometimes it’s helpful just to talk to someone about your problems.  Misery loves company so huddle up and help each other learn how to survive.

4.  Document everything.  Sorry to say this but sometimes it makes sense to document every bad incident or interaction with your boss.  Every time they lie, yell, embarrass you, or whatever the unacceptable behavior may be, write it down immediately so you don’t forget what happened.  Writing things down is important because you must capture as much detail as possible: the time, the place, who was there, what your boss was wearing, the project you are working on, exactly what was said or done by your boss and by you.  Detail is important because it lends credibility to whatever you are capturing.  Short statements with little detail look conclusory, so, if you are really faced with a major-league asshole boss, spend the time needed to write out what happened.  Then email a copy to yourself (at your personal email address) so you have a time stamp showing that the document was created at a certain time or date.  That way no one can claim you wrote it at a different time.  Similarly, as you go through the year keep a separate diary of your accomplishments, along with the times you came in extra-early, stayed really late, worked all weekend, and so forth.  At a minimum, this information about your performance will come in handy at review time.  And worst case is you will have a pile of ammunition in your favor if you find yourself being set up for a performance improvement plan (“PIP”) or otherwise have your efforts and accomplishments challenged or belittled by your boss.  I recognize that it’s sad that you may have to write things down like this but it may be your singular saving grace later if things really get bad.

5.  Does sticking it out make sense?   While it sucks to have a jerk boss, sometimes it makes sense to stick it out regardless.  Here are some reasons why:

  • Your eye may be on a bigger prize.  For example, you know down the road that if you obtain the right skills you can parlay that into a bigger role somewhere else.  If so, you’ll want to learn as much as you can, as fast as you can, even if you have to put up some pain.  Simply put, stay until you learn what you need to learn, then start looking move on to a better job with a better boss if the problems are not solved.
  • Consider what is it you like about your job?  If you like your company, your colleagues, your pay and benefits, your commute, work-from-home opportunities, the work you do, and other things, then all of that may outweigh working for a real asshole.   It’s difficult to find the perfect place the work, so if there are enough good things going on at your current job it might make sense to live with your boss’ awfulness.
  • Maybe you’re close to retirement, or you feel you need to stay put at your job until your children are out of the house, or until some other landmark event occurs, i.e., you are willing to “take one for the team” until the event occurs. Once you clear this hurdle, then you will feel free to make a change.  Sadly, sometimes events around you force you to accept less than desirable job circumstances.

Whatever the reason or the rationale you need to make the determination whether if, on balance, you’re better off staying with the idiot boss, at least for now.

6.  Talk with your boss.  This one is kind of scary because deep in your heart you don’t really think having a talk with your boss about their behavior is really going to make any difference.  But it might, and for that reason alone it is critical that you have a respectful conversation with your boss about the things he or she are doing that you think are unwarranted, unfair, demeaning, or just not right.  Before you go in, prepare carefully for the meeting. Do not try to wing it on the fly.  Write out the key points you want to make, but keep the list relatively short, i.e., just the important stuff.  Don’t create a giant list of everything that bothers you about your boss.  Be sure to have examples of what you are concerned with and not just generalizations about your feelings.  And when you are done with the conversation, good or bad, write down everything said and that happened.

If the meeting is a failure and the abuse continues, it’s time to consider going to the human resources department.  But, do not take this step unless you have had a conversation with your boss and nothing changes.  Going to HR first, without talking to your boss about your issues, is likely going to make things worse.  Additionally, do not go to see HR unless the problems are really bad.  Talking with HR because your boss yelled at you one time is not a smart move.  And, if your boss is really bad it may be that others are already raising issues.  You don’t necessarily have to file a complaint, you can ask the HR professionals for advice on how to handle the situation (and at a minimum, you are putting a marker down in the event you feel you need to file something formal down the road).  Moreover, this will be one of the times your written documentation will come into play.  The more detailed it is, the better for you and the issues you are raising.  One caveat to the advice about not going to HR first:  if the problem with your boss involves any type of sexual harassment or physical bullying then you should go to HR first (or otherwise follow your companies process for such complaints).

7.  Things to do.  There are several things you can do when things are going sideways with your boss in real time. The first and most important is take a deep breath think hard before responding to whatever it is he or she is doing or saying.  This is probably one of the hardest things to do in your work life, but when faced with a total asshole of a boss you need to consider the consequences of the next words coming out of your mouth.  If getting fired is not on your agenda for today, don’t take the bait.  Even if they are yelling themselves red in the face.  Saying “Yes, I got it” repeatedly in a calm voice can quickly diffuse the situation (even if you don’t really mean it).  If an unfair email from your boss comes into your inbox, wait as long as possible before responding and even then, if you’re upset, do not hit send for your response until you have had a chance to cool down and re-read what you wrote.  Sending any email when angry is a bad idea.  Once the incident is over (and you have documented it), when the next project comes your way ask your boss to give you their expectations as to what they want from you.  Ask lots of questions so you can make sure you are getting them what they want and how they want it.  If they only want full-margin, 12 pt. Arial font, on every document then give it to them.  What do you care?   I have even sent emails to my boss setting out what the assignment is and what they have asked me to do so if there is any disagreement they can weigh in before I get started.  Also, a little “sucking up” from time to time can’t hurt.  And, of course, the best way to silence a problem boss is to do great work and get great results.  In-house lawyers that deliver great results are gold.

8.  Things not to do.  When dealing with a jerk boss, there are a few things that you simply should not do.  While doing these things might make you feel better, they will not serve you well if push comes to shove.  Your boss is in a position of authority, and as such deserves a certain level of respect and decorum – regardless of how big of an asshole they are being.  Here’s the short list:

  • Don’t yell at your boss or raise your voice.  Stay professional at all times.
  • Never get physical.
  • Do not be a smart-ass.
  • Don’t trash your boss in the office.
  • Don’t trash your boss on social media.

9.  Go Zen.  Okay, it might be pretty damn miserable when you have to engage with your crummy boss daily.  Or, if you’re lucky, your boss is only a part-time asshole, say Tuesdays and Thursdays.  Regardless, one way to deal with a boss like this is to “go Zen.”  In other words, find something that can relax you and take your mind off whatever it is your dingleberry of a boss is up to today.  Practice “mindfulness” which is simply living in the moment (a form of meditation) and a way to reduce stress, improve mood, and spend less time dwelling on negative thoughts.  In other words, a way to calm down and see your boss for the comedic joke of a person they are.  Listen to music (I always went with Crowded House), find something distracting on YouTube (Funny or Die is good), or focus on something you are looking forward to, like getting home to your family.  The point is to find something that can get you through whatever bad moment you are experiencing with your boss.

10.  Quit.  When all else has failed and you are just utterly miserable you may have to quit your job.  You must decide if it’s worth your time and energy to keep going into the office.  Sometimes the assholes win.  Life isn’t fair, and neither is the real world especially in a high-stress environment like an in-house legal department.  That said, don’t be stupid about it.  If you’re going to quit, have something lined up and be sure it’s better than your current situation.  Also, don’t forget that “quitting” doesn’t mean you have to leave the legal department or the company, i.e., you can quit your current job and move into a different area of the department or the company.  A lot of in-house lawyers go into the business side of things.  This might be your opportunity to “quit” and stay put.


Sadly, there are no magic bullets for a bad boss.  Sometimes, those are the breaks.  The above gives you a number of things to try to make your work life better if possible.  As usual, most of it is common sense.  That said, their abusiveness should not be rewarded, so keep a record and go see HR if it gets really bad.  But, if none of these work for you, your only option may be to quit your job and move on.  If that is the case, just do it smartly so you can go out on your terms if possible.  If you’re looking for some additional advice, check out Robert Sutton’s “The Asshole Survival Guide: How to Deal with People Who Treat You Like Dirt.”  If you have a good boss, be extra appreciative because not everyone is so lucky.  And if you are a boss, don’t be an asshole.

Sterling Miller

April 30, 2018

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