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4 Tips for Dealing with a Difficult Boss
No matter what occupation you work in, you’ll always have a boss above you. How you handle that boss can make your life easier or harder, but sometimes managing them takes a lot more work than imagined. Here’s how to “manage up” a difficult boss to make your life easier.

1. Understand Thy Foe

Perhaps looking at a difficult boss as your enemy is a rather strong way of going about things, but Sun-Tzu had some valuable advice. He said that if you know neither yourself nor your enemy, you will probably lose all the battles you enter into. Know yourself but not your enemy, and you may win half of them. But if you know both yourself and your foe, you have the best chance of winning all your battles.

Apply this concept to your boss by learning how to speak his or her “language”. The better you can understand them, the better you can identify what it is exactly that’s making them difficult.

2. Turn Weaknesses into Strengths

The close-to-ideal employee will be able to look at their boss’s weaknesses and flip them on their head. Let’s say your boss is disorganized and can barely remember their mother’s own name, let alone her birthday. If it doesn’t interfere with your workload, have that information on hand without them having to ask for it. Yes, it does fall into the enabling category, but it’s a super easy way to keep them happy and off your back.

3. Keep Your Behavior Separate

It’s so easy to give in and shout or nitpick back at your boss, but sinking that low is an excuse and only has to do with you. We’re not saying it’s easy, but keeping your integrity is one of the most important things you can do.

As a side note, every wall and window has ears and you should assume you’re always being watched by someone or something. Act like there’s constantly a live-feed camera trained on you, and don’t let yourself slack off by taking longer breaks or lunches than you’re allowed, sneaking out for an extra smoke here and there, or under-performing. Your boss may have their life falling apart, but you don’t need yours to as well.

4. Be Straight Up and Honest

I’ll admit, I don’t have the easiest time navigating social situations and it’s taken a lot of trial and error to learn the smoothest ways at talking to people (something that I’m still not even close to mastering). One thing that’s been golden? Being honest with people and telling them, “Hey, I feel awkward about bringing this up because I know it’s a touchy topic, but I respect you and wanted to be as honest as possible.” It’s disarming and to-the-point, and lets the other person know that you thought long and hard about it.

Once you’ve gotten that out of the way, remember to use the “I feel that…” tactic, as in “I feel that you’ve been tense lately/under stress/something’s been going on” and ask what you can do to help. If your boss is dealing with the crisis of a lifetime, the last thing they’ll want is for you to be one more negative thing. And if you try and make their life easier, they’ll remember it gratefully forever. You can’t read minds and don’t know what exactly is going on, so just ask.

Getting through your workday is tough enough, and adding a difficult boss to the mix can really complicate matters. But if you follow these four tips, it can make your life a lot easier.


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