8 Ways You Can Win When Dealing With Difficult People Put these tips into action and see your life get a lot easier

We all have to deal with difficult people. They may be co-workers, clients, friends, family members, or lovers. We can’t avoid contact with them.

And with our narcissistic world being what it is, more and more difficult people are injected into the course of life every day. Our societies breed them. Here are a few of my tips on how to deal with the annoying trouble-makers we know are out there.

1. Do Their Thinking For Them

Difficult people don’t really like to think. They think they are “thinkers,” but the thinking usually revolves around the most banal of subject matters. What difficult people have, instead, are fixations: obsessions with how this is, how that is, how this isn’t going well, or how that isn’t going well.

Part of your job in the beginning in dealing with the difficult person is identifying his obsession. Find out the obsession, and you’ve gone far in learning how to deal with the person.

Difficult people also like to cause trouble: that’s why they’re called “difficult.” You need to be able to anticipate their trouble-making moves in the beginning before they make their move. That way, you can head off their little games before they even have a chance to implement them.

Think someone’s going to stiff you on paying a bill for services? Make sure he pays up front before you do any work. Think someone is going to forget an appointment date or time? Remind him in writing multiple times. Think someone’s going to have an issue with making payments to you? Make them use post-dated checks.

The possible examples here are endless. But the point is the same: anticipate the difficult person’s lame excuses or shifty behavior ahead of time, and head it off at the pass.

2. Flattery Is Usually A Sign Of Bad Things To Come

This is not always true, but it is often true. There is nothing wrong with people giving you compliments. But there is a certain type of difficult person who sees flattery as a substitute for upholding his end of the bargain. This type of person thinks that flattery is interchangeable with paying for services that you may have provided him.

And it is not.

With experience, you will be able to tell when compliments are sincere, and when they are not. In the meantime, you should get very wary whenever someone starts complimenting you in an unsolicited manner.

3. The Best Records Win

Difficult people can’t play their games when written documents are staring them in the face. Your job is to make sure that such documentation exists. There should be a paper trail for everything.

That way, the other person can’t wriggle out of his end of the bargain, or try to say something that isn’t true. Trust me, being good about this will save your ass many times in your life. Because difficult people lie all the time. You don’t want to be in a situation where it is your word against his. You want the records to do the talking.

Save all your emails, letters, faxes, and other documents. Scan things for electronic storage. Have back-up systems in place. Look, for example, at the recent developments in the Cosby case, which may turn on whether an “immunity agreement” was ever in effect.

If you can’t prove something with a written instrument, it’s close to saying that it never happened.

4. Be Nice To Difficult People

Everyone hates difficult people. I generally try to befriend them. Not all of them, of course. But sometimes I almost look on it as a challenge. Sometimes these people are so eager for any warm human contact that they will trip over themselves to return the favor to you.

I like to charm difficult people. Call me masochistic, if you want. Maybe I see it as a challenge.

And you just never know. Sometimes the people you think are the biggest assholes are the ones who actually help you the most. This has happened to me a number of times in my life. It’s strange, but it happens.

5. “Nobody Knows Nobody”

I like this little rule. I took it from the 2006 film Running Scared.

I love this crazy little movie. There is a scene when one character gives a little speech about how we never really know other people.

The idea is that anyone can be capable of anything. If you make this assumption, it will help you implement the other survival tips I’m writing about here. Be prepared for almost anything from anybody.

Even if you’ve known someone for a long time, you just never can tell for sure. It’s wise to be cautious, to tread carefully, and never rule anything out unless you are sure 100%. Because the one time you are not sure 100% will be the time it comes back to bite you in the ass.

So never completely turn your back on a difficult person.

6. Difficult People Need Some Skin In the Game

People are more apt to cooperate with you if they have some stake in the outcome. You’ve got to arrange your dealings with such people in a way that forces them to have such a stake.

The difficult person doesn’t care if he screws you over, but he will care if he screws himself over. So make him have some skin in the game. Make him invest some amount of time or money in the outcome. You should never care more about a difficult person’s problem more than the difficult person himself does. 

That way, he’ll be less likely to drop the ball.

7. Control The Flow Of Information

Sometimes bad news needs to be revealed right away. Sometimes it needs to be released little by little, like drops of water. And sometimes it will be better if it is delayed for a time.

It all depends on the type of difficult person you are dealing with.

8. Get The Monkey Off Your Back, And Put It On His Back

In every interaction with a difficult person, there is some “monkey.” I mean some problem, some issue, or some point of contention that is being dealt with.

We can see “monkeys” as friction points, issues, problems, hot-potatoes, and the like.

Everyone wants to dump the problem on you. It’s human nature. Don’t let the difficult person dump the monkey on your back. Or if the monkey has to be on your back for a short time, get it off as soon as possible.

These are my general guidelines for dealing with those insufferable characters in our daily lives. With some practice—and some luck—you’ll be able to navigate with, through, or around them, as the case may be.

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