Why Good People Become Evil Bosses

Three Stories of How Ordinary People Became Machiavellian

All I do is win, win, win, no matter what
Got money on my mind, I can never get enough.

— DJ Khaled, All I Do Is Win

Previously, I explained that assholes exhibit what psychologists call the “Dark Triad” of personality traits: psychopathy, narcissism, and Machiavellianism. While one is generally born a psychopath, and develops narcissism from early childhood, almost anyone can become Machiavellian given the right circumstances. Thus, I argue that Machiavellianism is the most dangerous trait of all, and is flourishing due to the Silicon Valley culture that promotes winning no matter what. The following is an answer to the organizational paradox of why good people become evil bosses.

Here are three archetypal stories of those who “break bad” into Machiavellianism.

The Hard-Driving Leader

iStock/Getty

My cell phone lights up on a Saturday afternoon with a text message that reads: “URGENT: Call me!” It was from Amy, a CEO I…