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

The Hard-Driving Leader

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 was coaching through the inevitable rollercoaster ride of startup life. Amy was smart as a whip, an optimist to a fault, and one of the most genuinely nice leaders I’ve known. As a young, first-time CEO, she has done an admirable job of building a first-rate company, and, more importantly, possesses the humility to seek help to fill in her blind spots. Today, her usual confidence was overshadowed by worry, as she revealed that her company was facing another sexual harassment complaint.

“I swear that 75 percent of my job as CEO is just fixing people’s problems,” she confesses. “I had no idea I’d have to deal with all this!”

“No one does,” I commiserate. “But the primary role of a CEO is to be Chief Psychologist. Often that’s recruiting, hiring, and retaining talent. But it also means fixing the people problems no one else wants to touch.” I ask her about her strategy, and I can hear the frustration rising in her voice.

“Look, I’ve tried to get HR to fix this. I’ve met with each employee personally, I’ve held three meetings, even tried moving people around. …I’ve done all I can. I’m going to sic our legal pitbulls on this to threaten the claim away.”

I empathize with her predicament: “You’ve clearly tried a lot of different solutions to address this. It’s not from a lack of trying.” And then I begin to gently share my advice with her. “But you’re confusing process with problem solving. All of your steps seem perfectly logical, but they’re actually an avoidance of the issue.”

Beyond the will to live and the drive to reproduce, one of the most powerful human motivators is the desire for approval. Most successful people were first motivated by praise they received from their parents at an early age. So it’s unsurprising that some people never quite outgrow it, and later seek approval from a surrogate parental figure: their boss. Few things are more depressing than seeing a 50-year-old executive, with their parents long gone, still striving to be whole in another’s eyes.

Bruce was that person. I was hired by a VC board member to interview him for a CEO position at a hot startup. On paper, Bruce was a seemingly consummate executive: wonderfully conscientious, meticulous at consensus building, and a fearless navigator of political waters. His bosses loved him, but his 360-degree reviews were a little more mixed, despite his efforts to carefully cultivate his reputation. I knew something was amiss when I interviewed his direct reports, the more deeply intuitive of whom said they just didn’t trust him.

Psychologists try not to have favorite clients, but Grace was admittedly one of mine. She was a self-described “Southern belle,” and one of the warmest and well-mannered clients I have ever coached. But that persona belied Grace’s fierce ambition. She graduated Vanderbilt law at the the top of her class, and was given two promotions in less than two years. Her future seemed bright and secure, but she hired me anyway to accelerate her growth. Because many clients I take on are dealing with significant issues, it provides me a nice balance to get to work with people who, like a professional athlete, just want to be better.

“That your ambition is a double-edged sword. What got you here won’t get you there.”

She nodded slowly, as if taking notes in her head. “Explain…”

“Your ambition brought you success, and you should be proud of that. But effort alone won’t necessarily get you to the next level. History has shown that unfocused ambition can sometimes cause people to make compromises.” I paused. “I’m curious. Has your ambition ever led you astray?”

“Wow.” I was awestruck. “You know, I take it back. There is another way to learn to be a good manager besides doing.”

“What’s that?” she asked, remorse written all over her face.

“By observing. Your manager showed you the meaning of grace even though you lied to him. Usually only loving parents can turn the cheek and show that kind of benevolence. You now know what a good boss and an evil boss are, and it’s up to you which kind of boss you will be.”

The tears swept down her face. She closed her eyes and nodded.