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The Jerk Whisperer: How to Have Good Conversations with the Worst Kinds of People

You’d think that some workplaces are exempt from power struggles, personality clashes, and interpersonal drama
by Sarah Moriarty | Apr 25 2016

Alas! I’m a psychologist who once naively believed that she had found one truly harmonious profession, only to completely rethink that notion just months into my practice.


Having studied human behavior, I know that there are some approaches that are more productive than others when it comes to having a conversation with prickly characters. Here’s how to talk with four difficult characters that you’re likely to run into in your day-to-day, at work or in social settings.

How to talk with a hothead

If you’re dealing with someone who’s quick to anger, empathy is the key. First, help the person label what they’re feeling. You could do this with someone who seems angry by saying: “I’m trying to get a sense of what you’re feeling and I think it’s anger. Is that correct? If not, what are you feeling?” Wait for agreement or correction, then get them to evaluate the level of emotion, by asking: “How [angry] are you?” Be prepared for an emotional response, and allow plenty of time for their answer.

Next, find out why they’re angry by saying something like: “And the reason you’re so angry is because.” Once they’ve answered, say: “Tell me, what needs to happen for that to feel better.” Then, assess what each of you can do to get there. By exercising such thorough empathy, your angry conversation partner will feel felt which will help them calm down and both of you move on to a productive conversation.

How to talk with a know-it-all

A surprising strategy for having a good conversation with a know-it-all is to boost their ego by agreeing with them. This is the opposite of what the person would expect, so it dials down their need to preen.

For example, if the know-it-all starts belittling others to feed their own ego, tell them you feel lucky to have them on your side. This curries you favor and builds trust between the know-it-all and you. Now, with an in, you can have a conversation with the armor off and even gently explain how their know-it-all behavior may push people away.

Actually, the same type of strategy works for the chronically sarcastic person. Like the behavior of know-it-alls, sarcasm is meant to be a defense mechanism, but usually just alienates others. Let’s say you have a sarcastic boss who is always questioning your professional capabilities. If they say something like, “I don’t know why I’m asking you, of all people,” respond with “Yeah, me neither.” A comment like that will grab their attention and perhaps even rattle their cage a bit. Having shuffled the figurative deck, you’re ready to have a human-to-human conversation.

How to talk with a manipulator

It’s common wisdom that the better you know yourself, the better your relationship with the rest of the world will be. And let me tell you–this is especially true when dealing with aggressive manipulators deft at zeroing in on your weaknesses. To deal with manipulative behavior, it’s important to know which of your character traits can easily be exploited by manipulators.

For example, if you need constant reassurance to feel valued and respected, you might be dependent on other people’s approval for your sense of self-worth. This tendency can be easily exploited by manipulators, who can offer you simple platitudes while treating you poorly at the same time. However, if you are aware of the fact that you crave this attention and accept it as part of your personality, you can better discern when you’re being manipulated, give yourself a reality check, and recalibrate before getting deeper in your conversation.

How to talk with a certified a$$hole

Don’t – run!

If the climate’s right, we can all behave like assholes every now and again. Certified assholes, on the other hand, are people whose asshole behavior is not a temporary outburst on a bad day, but a part of their character. These are people whose bad behavior is continuous and long term, so having a good conversation might be next to impossible. In the workplace, certified assholes are the ones who constantly interrupt others while they are speaking, violate other people’s personal space, insult and intimidate them, put them down, stare at them aggressively, or ignore them altogether. Assholes leave their victims angry, afraid and humiliated.

There’s also another unfortunate effect of being around assholes: If you work in a rude and disrespectful culture, you’ll soon get used to rudeness and lack of respect and might gradually also begin to exhibit those behaviors towards others. In other words, being an asshole is a highly contagious condition, so try to avoid assholes as much as possible. It helps to think of assholes as a virus — you’d avoid close contact with a colleague who has the flu, so treat people afflicted with assholism the same way. Make it your immediate priority to keep your exposure time as short as possible.

If you’d like to do further reading on having better conversations, these books are a great place to start. Bonus: they’re all on Blinkist!

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