How to Work For a Difficult Boss

If you’ve been employed for any length of time, chances are good you’ve worked for at least one domineering and tyrannical boss. It might have been that assistant manager you had as a teenager in your first job at the local grocery store, or now that you’re in your 40’s, your current micromanaging boss from hell that drives you insane. The point is, at some point, you’re going to have a manager that puts you to the test mentally every day. How well can you handle it?

Unfortunately, unless you won the lottery recently or are independently wealthy from that app you developed in high school, most of us need our jobs and just can’t quit. Our only choice is to gut it out and hope something changes. (“C’mon Powerball^™ … daddy needs a new life!”)  Reporting to a toxic boss can be challenging to say the least. Their command-and-control, dictatorial, and downright inconsiderate behavior isn’t only frustrating … it can be unbearable. But, don’t despair … there are things you can do to make your current work situation bearable, and possibly even positive. Because, if you can get that tyrannical boss on your side, life can be pretty sweet.

But before we get to our four steps, I can personally attest that this can work. I once worked for a man that was the poster child of the boss from hell. Think of an elderly male version of Meryl Streep’s, Miranda Priestly, in “The Devil Wears Prada” only without a conscience. We joked that our boss ate babies’ souls for breakfast every morning before he came into work. We also surmised that he was probably more than two thousand years old, but was kept immortal by that.

It took a few months of doing what I describe below, but all of a sudden, he started to come out of his office and personally compliment me on some ad copy that I wrote. He started calling me into his office to … are you sitting down … ask my opinion on how we should market a new product! Even better, he truly had been a great copywriter at one time and I got to the point where I could pick his brain about becoming a better writer. By the time I left that job a few years later, he had become more mentor than tormentor.

Here are four of the things that I did to turn the relationship with my personal tyrannical boss around. Hopefully, they work as well for you:

1. Keep your boss informed. No one likes surprises at work—especially tyrannical bosses. If your boss gets blindsided in a meeting by something you should have informed him about, it will be bad for you. Really bad. To make sure this doesn’t happen, keep him in the loop about everything. From the most miniscule detail to major project decisions, you need to keep your boss informed. These bosses are controlling, so you need to make them feel included in every aspect of your work. If you’re unsure about telling them something because you think it’s insignificant, err on the side of telling them.
2. Gain their trust. Trust is the hardest thing to gain from tyrannical bosses. Their one-sided decision-making process isn’t conducive to outside opinions. But if you work to gain their trust, they’ll be more willing to listen to your suggestions. Try to become the messenger for your coworkers. Let them know that you’re willing to communicate their problems and questions to your boss. It may be intimidating to be the one who relays everything to the boss, but many of these bosses lack people skills. So by acting as the buffer between your boss and coworkers, your tyrannical boss will begin to develop trust in you.
3. Do the dirty work. Though these bosses love to micromanage, they also see many workplace tasks as below them. While they may want to create the entire sales strategy for a new product, actually communicating that strategy to their employees is like pulling teeth to them. Instead, offer to do their dirty work for them and present the strategy to your coworkers. Whatever the undesirable task may be, offer them your services. They may not show it, but they’ll be grateful you did. With luck, eventually you’ll begin to get more tasks delegated to you and your reputation around the company will grow.
4. Express your feelings. Make the attempt to discuss your feelings with your boss in a way that is constructive and professional. In other words, don’t be whiny. Practice going over the key points of your discussion ahead of time. When you’re actually in your boss’s office, keep calm, remain positive and encourage an improved relationship between you two.

The best way to do this is to say something such as, “Sometimes I feel as though my work doesn’t satisfy you, or it’s consistently inadequate. Is there something I could fix overall, or steps I could take to address this?”  Keep focused on the work, not personalities. Calling your boss a “big doody-head” won’t help the situation even if it makes you feel better for a minute or two.

Ultimately, however, you have to know when it’s time to cut the cord.  It’s naïve to think that you can repair every relationship at work. Even though mine worked with my one boss, I had another one that I couldn’t fix no matter what I did. Luckily, she left after one year and one of the better bosses I’ve worked for in my life replaced her.

When you’re working for a tyrant, always have an exit strategy in your back pocket. First, decide what you want to gain from the job. It could be experience, improved skills, or a chance to build your portfolio. Then, figure out how much time you need to stay at your job to complete your goals.

If your tyrannical boss is so maddening that he or she literally makes you crazy, then you may need to risk the shaky job market and quit then and there. No job is worth putting your health at risk. While you may not be able to change your tyrannical boss, it is possible to manage him or her. Hopefully by following these four steps, you’ll make your workplace a little more bearable.