Don’t work with psychopaths

Unless you are a trained therapist.

Dumb Ways to Die

I saw a tweet today, asking “If you could tell one piece of advice to yourself at 21, what would it be?” and without hesitation I thought, don’t work with psychopaths. You’d think you could handle it but you’d be wrong. I always thought I could, and I was wrong. You can’t outsmart a pathology.


I learned about a management tool many years ago called the Delta File. The idea is to maintain a written document, for your eyes only, where you capture observed behaviors (and consequences) that you find objectionable.

The purpose is to understand, change or act differently should you find yourself in the same position. It allows you to reflect over time on actions that you find problematic; sometimes you learn that you were naïve and when presented in the same situation you then understand why a person acted in a certain way, other times you can make a different choice and rise to the occasion — it helps you prepare for that moment.

PS: Don’t ask me for my Delta File. It is and will always be private.

A short-term side benefit of the Delta File, is how it’s a great way to let go of tolerable crap you have to deal with. When you see something objectionable and there is nothing you or anyone can do about it, just writing it down and acknowledging it’s “a bad thing” can help you handle the emotional burden.

I wish I had used my Delta File more prolifically over my career because I might have learned earlier just how much damage working with psychopaths did to me in the long run.


I’ve always said I enjoyed working with “difficult teams” or “turn-around environments”; that’s because those are usually euphemisms for “egos and other extraneous stuff are getting in the way of getting real work done”. Diagnoses range from “poor communication” and “lack alignment” to “they don’t know what they are doing” and “it’s a shit show”.

We each have traits that we pride ourselves in. For some reason—which I have not fully examined—I have in the past prided myself in being able to handle bullshiters and megalomaniacs well. Not just for shits and giggles, but in the service of a good cause.

I have been told I am a good listener. This is often people’s impressions of folks who are just quiet so I don’t take this as great praise, but I have used that perception as a tool to do my work effectively.

When people feel comfortable talking to you (because they think you are a good listener or you are showing interest or whatever the reason), they are much more likely to be receptive to questions and criticism.

This is why it matters. Showering people with facts and counter-arguments is much less effective in persuading or pointing out a problem with one’s thinking, than questioning and helping one question their assumptions and assertions for themselves.

So that’s how I’ve always done it. I let people talk. A lot. I ask clarifying questions. This simple type of exchange allows people to find error in their conclusions as they dig deeper into their rationales. They are then able to recover for themselves. It’s the ideal outcome. I don’t have to tell them whether or not I knew there was a problem in the first place; there is no glory in the I-told-you-so.

This works really well for most people. But then there are the psychos. The egotistic, non-empathic and deceitful. I also let them talk. And for those who are malignant, the bullshitters, the evil, the intentionally harmful, I hear all the self-affirming tautologies, circular arguments and straight out lies. Most of them are rather charming, charismatic too (these are known and consistent traits of psychopaths).

I observe the arrogance, the deceit, the explicit language and framing choices. (In a somewhat bizarre way, it is so creative that it’s really interesting). I also ask clarifying questions. But here’s the thing: they are much better at this game than I am. More sophisticated. Remorse is not part of their repertoire. They are in it to win it, regardless of the reality of facts or the consequence of actions.

The outcome from this scenario is I absorbed most of the crap they ditched and nothing was changed. There was no new insight. “You win some, you lose some” has been my attitude in these moments. However, that’s the problem with working with a psychopath. You do this day in, day out and you don’t even realize how you are the one that’s internalizing all that, even if you are fully aware of their problem.


I read my Delta File today to write this post. It made me so sad and exhausted. I paused half-way and noticed the grimace on my face. I was relieving those moments; cringing, biting my tongue, seeing the knowing looks in other people’s eyes. I had to go outside and just sit for a moment. It made me think of how people experience post-traumatic stress disorder.

The psychos were far more traumatic to me than I even knew. Even a long time after the fact. Thinking about my time working with them (yes, more than one, sadly), specially after a long time working with them, I start to recall how my own behavior deteriorated. It’s embarrassing to admit. They enabled a terrible work environment. Gaslighting is the word du jour and very descriptive of the psycho co-worker or boss’s approach; they don’t always flat out lie (denying they didn’t say or do something they said or did), but they’ll tweak meaning. Over and over. You are the problem, you misinterpreted, you lost your cool, you didn’t give them a chance, you, you, you. It is so taxing. It’s beyond exhausting.

That burden is invisible—to yourself and to others, but no less a burden. And you think you can handle it. Letting one bad behavior go by for some greater goal seems worthwhile at the time. You might have handled the situation at hand, but don’t fool yourself that you were not affected by it. Or that you are letting the bad behavior “go by”. When it repeats itself over and over, you are taking it with you, not letting it go. You’ve come to expect it and you develop tools to go with it, but not to deflect it.

In the long run, we expect fairness, reason and civility. In the long run, you’ll see how you were deprived of these so frequently when working with a psychopath (and how you discounted these actions at the micro level), that you fail to acknowledge the aggregate effect, the macro impact on you.

“We judge people by their behavior, we judge ourselves by our intent.” The psychopath will try at all costs to convince you of their good intent and you will use all your energy to show how their bad behavior is not compatible with that. And you will lose.

The feeling stays with you far longer than the job or the project and it has nowhere to go. Anger, resentment, self-doubt. There are so many possible vessels to hold that damage.

Don’t work with psychopaths. The cost to you is immeasurable and as far as I have learned, the lasting impact irreparable.


Note: I am not interested in debating psychopathy or sociopathy. I am not a physician or therapist and not particularly interested in the nuances and varieties of this characterization. I am using this term because it best captures the traits that when combined are used to give this diagnosis of “psychopathic characteristics” to people. Also, a jerk is a jerk, not a psychopath.

On that note, do not confuse psychopathy with psychosis or mental illness in general. As I pointed out, I am using this term to encapsulate the egotistic, non-empathic, deceitful traits of people who are truly taxing and harmful to interact with on an ongoing basis, not those who are sufferers of conditions that stem from chemical imbalances, other disorders of various kinds and who struggle but don’t express what I’m encapsulating in this abhorrent behavior.

While psychopathy is studied by the same field as various mental illnesses, it’s explicitly different and unique, that’s why it’s characterized as such. Sadly mental illness, all too common, is often mistaken or misunderstood as the same or similar thing, causing people to exclude, discount and further classify sufferers as “less than” people. Don’t be that person.


Post-script:

I have also, fortunately, worked in psychopath-free environments. It’s AMAZING in contrast. It’s completely different from my experience in those other places; it gave me perspective and was a true tonic for my mental health. All challenges of any work environment still exist in places like that, but they seem more worthwhile by comparison. I highly recommend it. Also, they are hiring.