How to Lead a Difficult Boss

(Part 2 of 3 of my Leadership Series)

We’ve all had a difficult boss at one time or another. . . . you know, the one that gets under your skin or even makes you dread going to work.

I think most of the time we assume that organizational leaders become leaders, because they know how to be leaders.

In my experience, that is almost never the case.

The majority of the time people get promoted to leadership positions, because they were great individual contributors.

Unfortunately, most organizations do a great job training an individual contributor but do a poor job at training leaders.

So that terrible boss?

Maybe they don’t mean to be difficult or even want to be difficult. Maybe they just don’t know how to lead. Now don’t get me wrong. Some people purposely want to be hard to work with. I’m not talking about them. I’m talking about the majority of leaders who just don’t know how to do it.

I’ve always taken the approach that I get to train my boss how to rock at their job. Some tricks that have helped me do this:

1. Understanding their why. If your boss is pressuring you or putting unreasonable demands on you, more than likely they’re getting the same pressure and demands from their boss. Sometimes just understanding where they’re coming from and what they’re trying to accomplish can help you be more patient. It can also lead you to working with your boss to find a solution for everyone.

2. Ask clarifying questions and take good notes. Some leaders can be hard to work with simply because they’re not clear in their communication. Asking clarifying questions and following up with an email or a shared document with your notes gives your boss space and time to clarify their intentions and what they’re looking for.

3. Be honest with your boss. Sometimes the best path is the direct path. Tell your boss you're having a hard time working with him or her, but you want the situation to be better. Then come up with a solution together.

4. Take the high road. Don’t allow yourself to get caught up in bad behavior too including gossip, passive aggressiveness, resentment, and pride. Your personal brand is more important than getting the last word in.

5. Lastly, never ever accept abusive or demeaning behavior from your boss. Any behavior that creates an unsafe workspace for you or others in your organization is not acceptable. If the situation is really bad, make sure you’re working with your Humans Resources representative to ensure the best approach is taken.  

Not all bosses are created equal. Sometimes they need training and leadership as much as you do, but when you take the time to realize that they’re human too and that you can help them, you’ll see massive change.

(As seen on Present Future Foundation.)

Originally Published 4/9/21