I’ve got a confession… I’m a people pleaser. And most days, I’m still terrible at dealing with difficult people and standing up to strong personalities.

This has played itself out in dozens of different ways over my career. I’ve taken on too much work. I’ve left meetings only to ask myself, “Why did I agree with that? I don’t really think that’s the best strategy.” I’ve apologized in emails for being the “squeaky wheel” while waiting to get approval on a project. Over time, I’ve gotten really good at learning simply how to avoid working with difficult people.

But I’m working on it… and here’s why.

Why It’s Important to Learn How to Work with Difficult People

Here are two realities I’m learning when comes to working with difficult people:

1. If left unaddressed, the situation typically gets worse.

Difficult people have distinct personalities. They’re strong-willed, stubborn (aggressively or passively), and emotionally demanding. Some they thrive on conflict and debate. Others are inconsiderate or passively unresponsive.

Regardless of the specific traits they possess, I’ve often learned that difficult people don’t even realize they’re difficult. That’s why it’s critical to address the situation. They might have zero awareness about how their actions are impacting your ability to work together.

Learning how to address frustrations also helps you because it helps to get it out of your head. Unresolved conflict will fester to the point that you are miserable going into work each day.

2. There will always be “difficult people” to deal with in the workplace.

The reality is there will always be work relationships that are challenging. Difficult people aren’t going anywhere. Putting an anonymous note in the person’s mailbox is not a viable option. Placing a bottle of mouthwash on a coworkers desk is not an effective way of telling him his breath smells bad.

Learning how to navigate complicated work relationships and difficult people now will help you learn skills you’ll need for the rest of your career.

What I’m Learning About Dealing with Difficult People

While I’m definitely still in training when it comes to learning how to work with difficult people, here are a few principles I’m learning to make the process a little bit easier.

“Difficult People” Might Not Like Me… and That’s Ok

Wanting everyone to like me is one of the primary reasons I tend to give into what difficult people want or avoid having a conversation with them. But the truth is, not everyone will like you, and that’s ok. However difficult a person might be, we can still learn from them.

“Difficult People” Don’t See the World the Way I Do

The fact that people see the world differently is one of the primary causes of frustration amongst co-workers. For example — High D’s on the DISC Personality Test might get frustrated with Low D’s because they’re not working fast or hard enough. A High S might get frustrated because a Low S only seems to be concerned with finishing a project at the expense of others. One is task-oriented. The other is people-oriented. When we realize that we’re wired differently, we can be more understanding when a difficult person acts they way they do rather than being constantly frustrated by it.

“Difficult People” Might Never Change

In the past, I’ve hoped that “killing them would kindness” might help win-over a person and help them see the various ways they can improve. But I’ve come to realize that despite my best intentions, some people might never change. Learning how to interact and respond to difficult people is a lot more effective use of my time than covertly trying to get them to change.

I Might Be the “Difficult Person” Sometimes

If we’re honest, we might be the difficult person to work with in some situations. I’m sure there are plenty of things I’ve done in the past to cause my workers to be frustrated or annoyed. Working with difficult people takes humility times. Often, that humility is cultivated when we realize we can be just as difficult to work with in some ways.

Working with difficult people is one of the most challenging aspects of working in a business or organization. But the next time you’re tempted to write someone off as “impossible to work with,” remember these principles. Don’t be afraid to have a difficult conversation if necessary. But also embrace humility, recognizing none of us are easy to work with 100% of the time.

Photo by Samuel Zeller on Unsplash
Photo by Taylor Nicole on Unsplash


Dealing with difficult people is a challenge none of us can escape. If we're willing to try, however, there are ways to make it easier.