Dealing with Difficult People in the Workplace

Kevin Underhill

There’s no getting around it. You will encounter someone in the workplace with whom it’s difficult to get along. Because you’re a lawyer, that point could well come as soon as you walk in the door. And so, you will quickly need to develop skills for dealing with such people. Print out this guide and hang it in front of your face, or maybe tattoo it on the inside of your forearm, so you’ll know what to do in an emergency.

Have A Good Place to Hide

The best way to deal with difficult people is to avoid them. Your capacity to do this at work is limited, so don’t underestimate the value of a good hiding place. Remember, your colleagues are just as intelligent and terrified as you are, so the obvious places will go quickly. You don’t want to open a cupboard and see it’s already full of coworkers trying to hide, frantically waving you off. Time is short, and you just wasted some.

Remain Calm

Well, your failure to hide effectively means you now must confront this person. Now you must remain calm, and appear calm, which won’t be easy because you’ll be panting and sweating due to your frantic failed efforts to hide.

Claim to Have an Unpleasant Tropical Disease

Malaria is a good one because it explains the sweating and shortness of breath. Don’t panic and throw out something like ebola—that’ll draw way too much attention, and later you’ll have to explain your failure to die.

Try to Understand Their Motivations

Often people only seem difficult because you don’t really understand where they’re coming from. Instead of just reacting, try to imagine what’s motivating them. Or, if you’re not good at imagining things, maybe go through their trash at home to see what you can learn from that.


Explain Your Own Motivations

Someone who seems difficult may be reacting to a perception that you are difficult. Often the explanation is that this person was raised in a cult where the members informed on one another in a desperate effort to gain favor with the leader, thus developing an acute sense of paranoia, but it is also possible that there has simply been a misunderstanding. Remain calm and explain your position.

Attempt to Build Rapport

This may be difficult with those who are truly loathsome, but few people really are. Consider biting the bullet and trying to connect with these individuals on a personal level. Invite them to lunch, or to dinner, or to join the pit crew of your Formula One racing team. Anything will do—it’s the shared experience that matters. Don’t take this person to the opera, though, because opera sucks.

When You Get Mixed Messages . . .

Mixed or even contradictory messages are more common than you might think. Often, it’s easier to just ignore the message you don’t like and pretend you’ve both agreed to the other one. Most likely, the other person will either believe you or be happy to join you in pretending they never had that bad idea in the first place. (Not even kidding about this one. It worked during the Cuban Missile Crisis. Look it up.)

Remember, Life Is Short

This is important for at least two reasons. First, it will help with perspective. Life is just too short to get angry or upset every time someone is being difficult. Do the best you can. Second, because the most difficult people are probably older than you are, you can always cheer yourself up a little by remembering they’ll probably die before you do. It’s not ideal, but it’s something.


Kevin Underhill

Kevin Underhill practices in the San Francisco office of Shook, Hardy & Bacon LLP. He is, in fact, a partner. He also writes the legal-humor blog Lowering the Bar (