How to Work with Difficult People

Are you dealing with any toxic personalities at work, readers? Whether they're your boss, coworker, client, or subordinate, it can be tricky to know how to work with difficult people — both from an etiquette perspective, as well as the psychological ramifications — so let's discuss. Readers actually had a great thread a while back, so we'll start by rounding up their advice.

We've talked about what to do when your boss has it out for you, as well as difficult coworkers who throw temper tantrums, but not in a while. Readers, what are your best tips on how to work with difficult people?

How to Work With Difficult People: Readers' Tips

It started when a commenter had a question:

Does anyone have any good trainings or podcasts on working with difficult people? I want to get to the point where I can work well enough with some strong personalities at work (so: not optional or avoidable). I just get so nervous and worked up and it eats a lot of my bandwidth and I just feel fried. My actual daily work isn’t affected by them and I’m generally well-liked and of equal rank. Things are just contentious when we have meetings and I’d like to let things just roll off of me. I’m pretty good about not taking any bait or stirring the pot and ignoring snide remarks vs responding. I think of how some people work in customer service for airlines or other stressful jobs. Is it just a gift? Or also just a bit of a learnable skill?

Readers asked her to clarify what kind of difficult people she was talking about, noting that “frustrated people short on time/resources are different than inveterate jerks.” In her case: inveterate jerks.

Some of the best resources the readers recommended:

The Gentle Art of Self-Defense, by Suzette Haden Elgin

The reader recommended “The Gentle Art of Verbal Self Defense” — there is a classic version, as well as an 2000 version just for the workplace, which reviewers note is a workbook, so some self-reflection is needed.

One reviewer gushed over the book:

Amazing book…. how to communicate and be politely assertive and not get bullied or sucked into arguments. The author has several books in the series, all the same message with various examples and situations. Her sci fi writing is excellent too, worth checking out if you are so inclined. It does take some practice to actually make the techniques work.

Working With You is Killing Me: Freeing Yourself from Emotional Traps at Work, by Katherine Crowley and Kathi Elster

This bestseller is a “pragmatic and insightful guide” authored by a psychotherapist and business consultant to “teach you how to unhook from upsetting situations and eliminate your workplace woes step by illuminating step.”

They promise:

Through eye-opening quizzes, real-life case examples, and field-tested strategies, you'll quickly learn how to identify and handle any relationship that holds you back on the job. With your newfound emotional skills, you'll be able to:

• Manage an ill-tempered boss before he or she explodes
• Detach from annoying coworkers whose irritating habits ruin the day
• Defend yourself from idea-pilfering rivals
• Get out of the grip of toxic relationships
• Protect your personal and professional territory from “boundary busters”
• Break out of the limiting roles that box you in
• Parent your difficult employees to get the results you want
• And much more

The same authors also wrote Mean Girls at Work: How to Stay Professional When Things Get Personal.

Meditations, by Marcus Aurelius

The are actually a number of versions of this book, some allegedly adapted for contemporary readers — so poke around to see which one looks best for you. The reader who mentioned it quoted this bit:

When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous and surly. They are like this because they cannot tell good from evil. But I have seen the beauty of good, and the ugliness of evil, and have recognized that the wrongdoer has a nature related to my own – not of the same blood or birth, but the same mind, and possessing a share of the divine. And so none of them can hurt me. No one can implicate me in ugliness. Nor can I feel angry at my relative, or hate him. We were born to work together like feet, hands and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural. To feel anger at someone, to turn your back on him: these are obstructions.

More recommendations from readers on how to deal with difficult people:

• The Empathary (@empathary on TikTok) (I think Jennine has shifted to other projects, but you can still find her communication advice on TikTok!)
• Another reader recommended a workshop she took called “The Art of Productive Conflict.” She didn't specify which workshop, but it may be this one; there is a similar course based on the Crucial Conversations book.

Additional books and resources on how to deal with toxic people:

• Jerks at Work: Toxic Coworkers and What to Do About Them, by Tessa West
• Crucial Conversations: Tools for Talking when Stakes are High, by Joseph Grenny, Kerry Patterson, Ron McMillan, Al Switzler, and Emily Gregory
• Work Jerks: How to Cope with Difficult Bosses and Colleagues, by Louise Carnachan
• Outwit the Workplace Bully: 8 Steps You Need to Know to Reclaim Your Career, Confidence, and Sanity, by Dawn Johnson
• Rising Above a Toxic Workplace: Taking Care of Yourself in an Unhealthy Environment, by Gary Chapman, Paul White, and Harold Myra
• Udemy course: Dealing with Difficult People
• Psychology Today article: “20 Expert Tactics for Dealing with Difficult People”

How to Cultivate Detachment When You Work With Difficult People

One reader commented that when she's in a situation like this she thinks of customer service reps for airlines, who tend to be very detached and polite. This may only be possible when it's an outside policy you're enforcing — as one reader noted, “I think “it’s harder to let it roll off you when people are being a jerk about your work or something that really affects your performance.”

Readers had more tips on how to cultivate detachment:

When I worked with the public I’d have a physical reaction when someone would get testy with me. I’d flush, my hands and voice would shake, etc. Then I’d try to squash it and just make it worse.
It took a while but I was able to detach, like Anon says, and think “I’m having X reaction to Y behavior. That doesn’t mean I’m wrong, it’s just a normal response. I know what to do.” Which sounds clunky but it worked.

Another reader had some tips:

Two things that work for me. Calling out snide remarks under the umbrella of “I'm confused you would say x” or “did I hear you right about x, or am I confused” – it takes some practice in the out-Southerning the Southern by forcing them to politely own their comment in front of everyone. Also, I repeat to myself “your anxiety is not my anxiety” for short fused people. What I mean by this is starting to take a step back to see if someone is frustrated writ large at the situation, or frustrated at you. Nearly all the time, it is the former.

Make Outside Factors Clear

In the original commenter's case, she was in a position where she had to say no to things that people wanted because of other factors outside her control, and readers said to reframe it and express the frustration back to the actual source. For example: “Look, it sucks, I wish I could say yes to you but … there is no manpower to do the thing and we don’t have regulatory approval.”

More Tips for Working Through Difficult Situations

Writer Rebecca Berfanger had some great tips on how to work through difficult situations in general that we rounded up in our post on how to deal with extreme coworkers, including:

Remember the big picture. How does this job fit into your career path? Is it worth it to you to tolerate the extreme behaviors? Hopefully there are enough other things you like about the job: satisfying assignments, a good salary, likable coworkers, or other benefits. Plus, imagine what it will be like when you or the extreme coworker eventually moves on to something else.

Focus on your work. Your boss and coworkers expect you to always do the best job you can, which means limiting distractions. If it’s a loud person or someone who is always bragging about the sacrifices they make for the sake of this job, a good pair of noise-cancelling headphones can be your best friend. Even if you don’t listen to anything, it can send a clear signal you are focused on your task at hand. (See also: how to discourage chatty coworkers.)

Ask to be relocated. Depending on the size of your office, you might be able to request a change of scenery—away from the extreme coworker. You might end up with a smaller space or a longer walk to the printer, but a little physical distance can make a world of difference. The reason for your request can be anything from wanting a space closer to a window or farther away from an area known for being loud (break room, elevator bank, copy machine, conference table, etc.). If you feel comfortable enough telling your supervisor the real reason, he or she might be able to come up with other solutions to help you concentrate on work.

Practice self-care. If you can't escape the extreme behavior when you are at the office, focus on what you can do outside of work to handle the stress of working with an extreme coworker. For instance, social workers and therapists who have accepted primary and secondary trauma as a part of the job also know that self-care is key (check out these TED Talks about self-care for ideas). Making time for therapy can also be helpful. Self-care could also be a “meeting” on your calendar for a short walk outside for some fresh air (maybe sneak out the back), or asking a (non-extreme) coworker to grab a coffee with you.

Move on. As we suggested in the difficult coworkers post, if working with this one person is bad enough, it might be time to seek out other opportunities. Also, if what you consider to be extreme behavior is what is expected in your office, this is probably not a good fit for you.

What are some of your best resources and tips on how to work with difficult people?

Stock photo via Deposit Photos / Milan Markovic.

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