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My Strategy for Dealing with Difficult People

How to deal with difficult people? It’s one of the most frequent questions I’m asked in my workshops and by readers, friends, and grad students. Here’s my strategy for dealing with difficult people and why it so consistently works.

Occasionally I am difficult. I don’t set out to be difficult and I may not even consider myself as “being difficult” in that moment. But I can tell by the other person’s reaction that they are considering me difficult.

Does that make me a difficult person? Probably not, because I am only occasionally difficult and that is human nature.

What if I am repeatedly difficult with the same person but not with most others in my life? Does that make me a difficult person? Probably not, because it is just one dynamic that I handle poorly.

What if I am repeatedly difficult with the same people in a specific setting, but not with others in my life? Does that make me a difficult person? While a few might say yes, most would probably still say no, because it’s a certain context that’s bringing out the worst in me but I am not routinely difficult with most people in my life.

So where is the tipping point? What does it take for someone to deserve the brand of “difficult person”? When I ask this question in my workshops, people often reply, “When someone is difficult with most of the people in their lives with some frequency.”

That seems a reasonable answer, but it has a significant problem associated with it: How can you know it’s true if you are not with that person all the time?

The problems with “dealing with difficult people”

Since it’s rare to be with someone in all parts of their life and most of the time, you can’t really know and so it would be much fairer to consider them not as difficult in general but difficult to you or in certain settings or circumstances.

Psychologist Jeffrey Kottler put it this way: “Every person you fight with has many other people in his life with whom he gets along quite well. You cannot look at a person who seems difficult to you without also looking at yourself.”

So one problem with trying to figure out how to deal with “difficult people” is that it’s virtually impossible to fairly and legitimately know they are difficult people for sure. That thinking error (“He’s difficult to me right here right now so he must be a difficult person”) then spawns myriad additional problems:

    • You fall victim to confirmation bias, the tendency to notice and/or interpret information in a way that confirms your preconceptions (“Look how difficult they’re being again! See, I knew I was right about them”). Since you’re subconsciously screening out information that contradicts your conclusion, you’re missing part of the story.
    • You fall victim to a category error, a thinking error that occurs when you over-rely on a category you’ve put someone or something in. By placing them in the category “difficult,” you inadvertently limit your ability to understand them more fully and may well fail to notice all the additional categories they also fit into.
    • You trap yourself in a reflexive loop, another cognitive error. Reflexive loops occur when you select partial data from your observations (“She’s being really obstinate…”), draw conclusions as a result of the selected data (“…wow, she’s pretty difficult…”), and use those conclusions to generate a belief about the person or situation (“…so she must be a difficult person”). Reflexive loops feed on themselves and strengthen the belief, even though it was initially generated by only limited data.
    • You increase resistance by diagnosing their frailty and acting on that (mis)diagnosis. I find that people don’t much care to be worked on (do you?); they prefer to be worked with.
    • You’re still stuck even if you’re right. If they are that rare animal, a truly difficult person, why is it that you think you’re going to change them into a less difficult person? How will you undo decades of habit? And why should they listen to you?

A better alternative: Dealing with difficult behaviors

My strategy for dealing with difficult people is this: I don’t try. I recognize that the difficulty I’m experiencing with them is in “the between,” to borrow a phrase from Jonathan Haidt. “The between” is the space between us.

Instead, I ask myself what behavior that is irritating, obstructing, or confounding me or someone else. Focusing on a specific behavior has far better outcomes because…

  • A person who is unwilling to negotiate a change in who they are may nevertheless be willing to negotiate a behavior change when they understand the behavior is creating a problem with consequences for them.
  • I can always learn more ways to address difficult behaviors and there is a lot of good material already out there on the topic (see below).
  • I give myself more margin because, frankly, sometimes something I’m doing is feeding the difficult behavior.
  • I prevent myself from the limiting traps caused by the thinking errors described above, which in turn allows me to notice information that may be crucial to resolving the conflict.
  • If they refuse to negotiate a change in the behavior, I have the opportunity to converse with myself about how crucial that change is to my relationship with them, then make choices accordingly.
  • I may recognize that the difficult behavior is time or context-related. If it is, then a different time or place may result in a far more fruitful conversation.

Dealing with difficult behaviors

I’ve written a fair amount here on difficult behaviors during conflict and I’ll no doubt write more. Here are some audience favorites:

  • The primal roots of blame and defensiveness
  • Managing difficult behavior: Lowest level of intervention first
  • High conflict personality? Not so fast
  • Just be reasonable
  • Trigger stacking
  • The fist press exercise
  • Want to influence behavior? Stop telling and ask these types of questions instead
  • The Missy Method for reinforcing good conflict behavior

Tammy Lenski

Dr. Tammy Lenski helps individuals, pairs, teams, and audiences navigate disagreement better, address friction, and build alignment. Her current work centers on creating the conditions for robust collaboration and sound decisions while fostering resilient personal and professional relationships. Her conflict resolution podcast and blog, Disagree Better, are available at… MORE >

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