In “The Performance-Values Matrix,” I argued that the biggest reason company culture degrades is that companies hire, retain, and promote “assholes” (mercenary employees whose lack of empathy causes interpersonal issues). I also introduced the Performance-Values Matrix as a reinforcement system to assess and address this very problem. Let’s now dive deeper into a clinical understanding of “asshole” behavior and how it can be carefully managed in a corporation.

Part I: Anatomy of an Asshole (The Dark Triad)

“Asshole” is not a term I use clinically or scientifically, but rather commonly because it provides a shared understanding of something you “know when you see it.” My goal here is to offer insight into and clearly categorize a pattern that you probably intuitively recognize.

Clinically, there are three distinct types of socially aversive personality traits, known as the “Dark Triad”: psychopathy, narcissism, and Machiavellianism. These traits are dimensional in the sense that all of us fall somewhere on the spectrum, but only those who are very high in the trio of traits can be considered diagnosable with antisocial personality disorder. If you’re curious, you can take the online Short Dark Triad personality test to see what percentile you exhibit in these three traits, compared to the general population.

The key to understanding the Dark Triad is that while all three share a callousness toward others that encourages manipulativeness, they do so for distinct reasons. Psychopaths are driven by short-term tangible rewards and engage in reckless, antisocial behavior to get them. Machiavellians are fueled by long-term tangible rewards and will strategize schemes to get them. Narcissists are motivated by whatever boosts their ego, whether it be tangible rewards or simple praise that validates their idealized self-image.

Psychopathy, aka the Gordon Gekko

Psychopaths are your typical movie villains. Their emotionality is callous and aggressive (manifested as angry outbursts or even physical violence with little remorse) and their behavior is impulsive and irresponsible (often blatantly disregarding the safety of themselves or others). They gleefully defy norms and laws, and use deceit and manipulation for profit or, even more alarming, self-amusement.

Though only 1–2 percent of people in the general population can be clinically diagnosable as having antisocial personality disorder (as stated in “The Diagnostic and Statistical Manual of Mental Disorders,” or DSM-5, a widely respected mental health atlas), they are unfortunately overrepresented in corporations, especially among CEOs. Favorite cinematic depictions of psychopaths in corporations include Gordon Gekko in the 1987 film Wall Street and Patrick Bateman in 2000’s American Psycho.

A unique aspect to psychopaths is they tend to have a short-term focus: for example, they will lie for immediate gratification, even if those lies compromise their long-term gains. Other short-term behavior such as recklessness and thrill-seeking tends to drive ambitious and reckless criminal behavior. For further reading, I recommend the book, Snakes in Suits: When Psychopaths Go to Work.

Machiavellianism, aka the Frank Underwood

The Machiavellian is a strategic, calculating manipulator who believes that the ends justify any of the means. While as manipulative as psychopaths, Machiavellians are far more future-oriented: planning ahead, forming alliances, and carefully maintaining their reputations. They tend to achieve the latter by shielding close friends and family members from their nefarious ways.

Unlike psychopathy, which is partly genetic and rarely remediable, Machiavellianism can be more of a fluid state as opposed to a permanent personality trait. As the Milgram and Stanford prison experiments suggested, normally prosocial people can act in surprisingly Machiavellian ways when in certain situations, under certain conditions. In fact, I have seen corporate leaders, who appear to be genuinely kind in their personal lives, act surprisingly Machiavellian when their companies are put into difficult financial dilemmas (e.g. hiring and refusing to fire mercenary employees). Corporate culture, particularly in Silicon Valley, encourages such behavior by glorifying leaders that “do whatever it takes” to ensure their company survives and succeeds.

The irony is that startups say they love “hustlers” (i.e. proactive employees that do whatever it takes to get the job done), although the term hustler also means someone who cons and cheats others. Coincidence? Probably not. For further reading, I recommend the classic books Machiavelli’s The Prince and Sun Tzu’s The Art of War, and for a more modern rendition, Robert Greene’s The 48 Laws of Power.

Narcissism, aka the Tony Stark

Most people are familiar with the most obvious features of narcissism: grandiose self-confidence and self-centeredness, which comes off as smug and self-serving. However, the narcissist is actually very insecure and on a never-ending quest for ego-reinforcement, which includes going so far as to deceive himself. Narcissists seem to believe their own boasts and feel entitled, even when it can be verified that they are exaggerating their competence.

Emotionally, narcissists feel anger and aggression if their fragile ego is threatened, in what’s known as “narcissistic rage.” Given that they cannot be vulnerable enough for true intimacy, their relationships tend to be unempathetic and superficial. Behaviorally, they tend to act antagonistically toward others — manipulating, lying, and threatening their way to their desired results — and engaging in uninhibited acts that are irresponsible, impulsive, or risky to seem exciting or daring.

It is important to note that some degree of ego is actually healthy and necessary to form a resilient sense of self that allows one to persevere through trying times. The distinction is that healthy self-confidence is an attitude based on mastered accomplishments, adhered values, and respect toward oneself and others, while narcissistic self-confidence is actually a psychological defense against underlying inadequacy (which is why it’s referred to as “malignant self-love”).

At some point in their lives, about 6 percent of people will meet full criteria for narcissistic personality disorder, with more men (almost 8 percent) than women (almost 5 percent) qualifying. As with the rest of the Dark Triad, narcissists are overrepresented among leaders , especially leaders of nations. For a psychoanalytic perspective on how narcissism develops, I recommend Alice Miller’s book, The Drama of the Gifted Child.

Part II: The Accidental Asshole (High-Functioning Autism)

Distinct from the Dark Triad spectrum is a condition that can actually be useful for work, called Autism Spectrum Disorder, in which high-functioning cases were formerly known as Asperger’s syndrome. People on the autism spectrum are not usually assholes. But they share an impaired sense of empathy that can make them seem like assholes.

The key distinction is that people with Dark Triad traits are often insensitive to others, while people with autism can be indifferent. They have difficulty picking up on cues that would prompt them to do or say what’s considered socially appropriate. One of the best showcases of this distinction is in the movie The Social Network. To be clear: I am not attempting to diagnose Mark Zuckerberg (who was my Harvard classmate and a nice guy), but am discussing his somewhat fictional movie representation in line with the rest of this post.

The film starts with Mark and a fellow college student Erica going out on a date. She quickly breaks up with him because he says offensive things, which she interprets as him being an asshole (i.e. Dark Triad spectrum). However, by the ending scene, Marilyn, Mark’s attorney, recognizes that he’s less an asshole, and more painfully oblivious (i.e. on the autism spectrum), and is trying to mimic the hard-nosed behavior of what he believes other CEOs do.

Opening scene [Erica]: “You are probably going to be a very successful computer person. But you’re going to go through life thinking that girls don’t like you because you’re a nerd. And I want you to know, from the bottom of my heart, that that won’t be true. It’ll be because you’re an asshole.”

Ending scene [Marilyn]: “You’re not an asshole, Mark. You’re just trying so hard to be.”

Cognitive vs. Affective Empathy

Most people think of empathy simply as understanding others, or confuse it for sympathy. But psychologists distinguish between two main types of empathy: cognitive and affective. Cognitive empathy is the capacity to understand another person’s mental state, while affective empathy is the capacity to respond with an appropriate emotion to another person’s mental state.

For example, if you see someone fall and rip their jeans, experiencing cognitive empathy would be to place yourself in their shoes and realize the other person would likely be thinking “How embarrassing!” But affective empathy would be to actually experience feeling embarrassed for them along with a compassionate desire to help them in that moment.

As seen in the matrix below, people on the autism spectrum have impaired cognitive empathy and intact affective empathy, while people on the Dark Triad spectrum have the reverse: intact cognitive empathy and impaired affective empathy. Thus, people on the autism spectrum have interpersonal difficulties because they have difficulty understanding social situations, while people on the Dark Triad spectrum understand social situations well, but often have antisocial objectives. So people on the autism spectrum are asocial, while people on the Dark Triad spectrum are antisocial. It is also possible to have both autism and Dark Triad spectrum traits, and thus feel little cognitive or affective empathy.

Unempathetic Partners in Crime

It would seem that people with Dark Triad and autism spectrum traits would not likely be friends, given that people with Dark Triad traits can often be (superficially) charming, while those on the autism spectrum often have trouble fitting in socially. But these individuals often become partners in crime because their respective deficits in empathy allow them to work together in a strangely parasitic symbiosis. This metaphor is useful in understanding how their motivations differ at work:

“[People on the autism spectrum are] focused on ‘building a better box’; on the box itself, on how it’s made, on improving it, on what else it can be used for, on other boxes like it, and often wants others to hear about the box and their ideas, share in their enthusiasm, or at least be understanding or respectful of their enthusiasm about ‘the box’.

[In contrast, people on the Dark Triad spectrum are] focused on getting credit for ‘building a better box’ (whether they built it or not), getting seen as the ‘box-builder’, getting credit for being the Most Expert Box Builder, how the box can be used to make themselves money or to further their personal agendas, how to hide the fact that someone else built the box.”

My favorite movie portrayal of this dynamic is from the 2013 biopic, Jobs. In a dramatic scene, Steve Jobs convinces his friend Steve Wozniak to help him design a new video game for Atari, but lies to him by offering to split a $700 bonus (which was really $5,000). Years later, Wozniak found out about Jobs’ duplicity while reading a book on Atari’s history and was brought to tears.

Thus, those with Dark Triad traits tend to prey on people on the autism spectrum and use them as “sidekicks” to exploit their loyalty and talent. However, when the person on the autism spectrum figures out their true intentions, the Dark Triad person often turns on them in order to avoid being exposed. For example, a manager can influence an analyst to produce promising but questionable data to push their own agenda, which later results in a falling out between the two (often after irreversible damage is done).

Part III: Managing the Darkness Within

Even if they are competent, people who strongly exhibit Dark Triad traits at work need to be remediated or separated in order to maintain the company’s culture. However, if they stay, it is critical to recognize the degree to which they are socially and occupationally impairing, and take swift steps to mitigate damage when social dynamics become disrupted or exploitative. In my experience, Dark Triad employees work best at values-congruent companies if they are in niche roles that accentuate their strengths and minimize their weaknesses.

They often work better as individual contributors, given that empathy is a key aspect of being a successful manager, and the perception that your manager genuinely cares about your well-being is one of the strongest predictors of employee job satisfaction. Thus, individuals who strongly exhibit Dark Triad traits and have to regularly interact with others often need to be specially managed in order to ensure both their personal success and the well-being of those around them. Using the Performance-Values Matrix is a helpful management structure to reinforce prosocial behavior and punish antisocial behavior.

It’s important to note that there are exceptional CEOs with these traits that are still wildly successful and admired. In the case of Steve Jobs, he exhibited these traits, but he was also an incredibly talented visionary with a complementary team. Being surrounded by operational leaders with high emotional intelligence (EQ) can help balance the high IQs and temperaments of visionary CEOs and steadily steer unicorn companies forward.

In case you take such success as an excuse to flaunt your darker traits as a leader, just remember: you are not Steve Jobs. Unlike a renaissance prince, as a CEO, it is much better to be loved than feared. Effective leaders must embody the light by understanding and managing the darker traits of their employees.

Continued in Part 3: Why Good People Become Evil Bosses