4 Ways to Deal with a Difficult Boss

Got a difficult boss? After a recent post on this topic I was flooded with private messages from people in the same boat.

hellfrigidThey’re working for someone who they aren’t getting along with and:

  • can’t tolerate the stress much longer,
  • don’t want to start looking but fear they must,
  • could lose their job if the problem continues

Basically, they’re in one “heck” of a dilemma and could really use some help.

Can you relate?
– You’ve always been successful, but somehow now you can’t do anything right.
– The more stressed you get, the more mistakes you make.
– You’re afraid if you do nothing, things will get worse.
– Going to HR is not an option.

There’s nothing worse than being in this situation. So let’s work together to help you take control and do something constructive to make things better, shall we?

First, ask yourself if you’re dealing with someone who has an opposite personality style from your own. Many times, this is the crux of the issue, so learning more about what motivates this person can help you work around their peculiarities.

Are they controlling or are they so loosey-goosey that you never know from day to day where they’ll stand on one issue or another? Are you a results-oriented person and they need to run everything through a committee? Do they take things super-serious but you’re more relaxed and don’t like to sweat the small stuff? Are they a driver with few concerns for people issues and you’re all about the relationships?

So profile them. Figure out who you’re dealing with and plug their personality into one of those assessments you took years ago. Then bump your personality style up against theirs. See where you fit and where you clash. (If you want to take an assessment, let me know and I can get you one that’s inexpensive.) What are the big sticking points and what are the minor annoyances you can put up with?

Option 1. Give ‘em more of what they need. You heard me. Make up your mind to stop fighting them and try to do things their way. I’m not saying it’s going to be easy. It could be darned difficult. But they are the boss and in most cases, they’ll win this game. You’ve got to decide what it’s worth to you.

Once you decide to play along, life might just get easier. I’m not trying to get you to become another person or compromise your values. It’s just survival. You’ve probably got a family to feed. And it won’t do your career any good to go hopping from one job to another because of a bad boss. The sooner you can lift some pressure off your shoulders, the brighter life will look, the fewer  “mistakes” you’ll make and the happier everyone will be.

Now, let’s assume that this is either something you cannot or will not do OR that it doesn’t work. The pressure doesn’t let up. You’re still in that proverbial dog house. Their behaviors compromise your ability to do your job. They act in a way that puts you or others at risk. These are serious issues, which call for a direct conversation.

Option 2. Then ask for what you want. Be very specific. State the facts. Don’t go “below the waterline” and bring up personality quirks or make broad, sweeping generalizations about their intent. You can’t peer inside their head. Tell them you are committed to make the relationship work but you fear it’s on a shaky path. You want to make things better. You don’t want to add to their worries or concerns. You need to know what they want you to do differently. Just the fact that you have this conversation might be a wake-up call to them. They go about their business each day with little understanding of the impact they’re having on others. Your discussion might cause them to self-evaluate.

Option 3. Coach them. Do it by asking questions that start with “how” and “what” so you don’t put them on the defensive. Ask them to describe the results they’re trying to get with that plan of action. Start by saying, “Help me to understand what we’ll achieve if we do X.” This will take patience. You may get small, incremental improvement over a long period of time. They may take two steps backwards once in a while. Remember that human behavior is a tricky thing and people don’t change overnight. The key here is that they believe you have their best interests at heart. If they feel you’re on their side, this will go much smoother. Do not be condescending. No eye-rolling, okay?

Option 4. Brush up the resume and break out the rolodex.

In the end, you are the only person who can decide the best course of action. You know your threshold for stress. But I hope you will consider many options before you choose your path. There isn’t just one right way to cope with a difficult boss. Give one option a try and if it doesn’t work, try something different. But don’t let yourself get pushed into a situation where you will be the loser. I want you to be happy and successful!

Many of you have been down this path and lived to talk about it. Care to share any ideas or suggestions? Please add them in comments.


  1. Laura Benjamin says:

    Joe, thanks for the in-depth description of all that could certainly go wrong. This story shows there are no guarantees and despite our best efforts, having a good boss is worth it’s weight in gold. Some say they’d rather have a great boss and a job they aren’t crazy about than the other way around. I appreciate you taking the time to write and wish you the very best!