How to Survive a Difficult Boss

We've all had them: bosses who are micromanagers, who are never satisfied, or who seem to enjoy making our lives difficult. While it's impossible to change your boss's personality, there are a few things you can do to make your work life more manageable.

Document Everything

Delete nothing. Keep a detailed record of all your communications with your boss, including emails, texts, and voicemails. This will be helpful if you ever need to prove your point or that you had, or didn’t have, certain interactions with your boss.

Make Notes to the File

In addition to saving your written communications, it's also a good idea to make notes to memorialize conversations and phone calls. This means contemporaneously documenting writing your interactions with your boss, particularly verbal communications that would not otherwise have a written record.

So, if your boss casually mentions as you’re passing each other in the hallway that it’s OK for you to do something or not do something, either send them a quick email confirming what was said, or make a written record for yourself. This can be helpful in protecting yourself and your reputation in case your boss attempts to rewrite history or deny what was said at some point in the future.

Confirm Receipt of All Messages

When you receive a message from your boss, be sure to confirm receipt. This literally can be an email response saying “Confirming receipt. Thanks.” This will show that you're paying attention, that the boss is being heard, and that you're taking their requests seriously.

Repeat and Confirm

After your boss gives you instructions, repeat them back to them to make sure you understand what they're asking. This may help to avoid misunderstandings and mistakes.

Ask for Prioritization

If your boss gives you several projects or tasks, ask them to prioritize the order in which they want them completed. This will help you to deliver the results your boss wants.

A Deeper Understanding

It's important to remember that your high-maintenance boss may simply be operating out of fear. They may have been disappointed by people in the past, leading them to micromanage and demand perfection. While this doesn't excuse their behavior, it can help you to be more empathetic. 

When I was a young law firm associate, I worked for a very difficult partner. One day, I very nicely told her that when she asks me to do something, she should know that it will get done. She responded that she had so many bad experiences where she was burned by associates in the past, that she had trouble trusting people.

By understanding the root cause of her behavior, I was able to approach her with a bit more empathy and patience. While it didn't change her personality, and I never liked working with her, it did help me to manage our relationship, and my stress level from working for her, a little more effectively.

The Bottom Line

Working for a difficult boss it’s never fun, but it’s an unfortunate reality in many workplaces. By improving communication, bringing a bit of empathy to your interactions, all while taking steps to protect yourself and your reputation, you may make the situation easier to deal with.

Helping you Thrive,

Judy

Founder, Selby Strategies

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