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

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.”

Her attention perks. “Which is what?”

“Doing the hard thing: taking responsibility. You didn’t cause this, but you did let this situation fester. Don’t hide behind your legal team. Own up to it and stop it from continuing one minute longer.”

She sighed a painful sigh of recognition. “You’re right, but I just can’t deal with this right now. Our lawyers can. I’m going to take an Ambien to try to get a few more hours of sleep. I’ll call you on Monday, I’m sorry.”

I recognize Amy’s pain. It’s the feeling of burnout. As a clinician and executive, it’s interesting to see that empathy burnout is commonly acknowledged among those in the medical field, but virtually ignored among CEOs. This type of burnout is characterized by the trifecta of emotional exhaustion, detachment, and low sense of accomplishment, and occurs when people feel overwhelmed by the demands of caring for others, given limited time and resources.

The original hypothesis was that doctors experienced burnout due to “compassion fatigue” or having too much empathy, so they were bizarrely cautioned to not get too attached to their patients, lest they experience burnout when or if their patients don’t get better. A more mature explanation of burnout has emerged though: Chronic stress ends up diminishing empathy, and it’s actually this lack of caring that contributes to burnout. So rather than avoiding empathy, a more cognitive empathy should be cultivated to prevent burnout.

While everyone knows CEOs can be overworked, what’s less acknowledged is that the burden of being responsible for so many people also chips away at their empathy and leads to burnout. When that happens, Machiavellianism can set in, and they start to lead from a place of defensiveness instead of company values. Amy’s capacity for empathy was intact, but as she rose from being an individual contributor to managing hundreds of employees, her patience wore thin from being burned one too many times. While she genuinely wanted to improve her company’s culture, she felt her first priority was to keep the ship afloat. Perhaps it was, but she failed to see that mutiny was as big a threat long-term as running the ship aground.

In our coaching sessions, we worked on reducing her stress and rebuilding her empathy by reconnecting with the original values the company was founded upon. I knew our work was done when she forwarded me an email to a direct report, which showed she was no longer trying to avoid through delegation. The email started with: “I was wrong. I feel terrible about it. Let me find a way to make things right.”

The Conniving Executive

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.

“It’s like talking to a robotic AI chatbot,” one said. “All the right words come out, scripted just for you, but it doesn’t really care.”

In my initial conversation with Bruce, he guardedly admitted he was aware of his reputation, but attributed it to the fact that he was a more formal professional from a different generation. His “millennial employees” just couldn’t relate. But my read was that he was a mercenary who could run a militia, but whom you could never trust with anything you truly cared about.

Let me share a telling story: Everything had gone well at Bruce’s current organization until it was about to acquire another company, and he was put in charge of the merger. He told a talented member of another team this confidential news, but swore her to secrecy, making her promise not to tell her boss. Her boss ended up finding out from someone else later on.

When I confronted him about this, I already had my suspicions about his intentions. He was too smart and deliberate to make a simple mistake like this.

“So why did you put your colleague in the awkward situation of promising to keep your secret from her boss?”

He gave a calculated response. “I trusted her to stay silent, but I didn’t trust her boss to. He cared too much about the people who would be impacted.”

I countered. “No, you were grooming her as an abuser would, because you wanted to poach her later. If her boss never found out, she proved her loyalty to you. If she confessed to her boss, you know she could never become your trusted foot soldier.”

His smile turned into a frown, but I continued. “But if her boss found out about your arrangement from someone else, he would no longer trust and promote her, which would drive her into your arms for a promotion. Her lose-lose was your win-win.”

From the anger flaring in his eyes, it was apparent that the jig was up. “You cannot tell the board this. It’s my time to finally be CEO. I’ve earned it!”

I paused, letting the silence stretch out between us. “Actually, the board already knows. They didn’t hire me to vet you. They hired me to convince you to take the job anyway.”

“What do you mean, anyway?”

“What they didn’t tell you yet is that the company is going to be shuttered next year because of lawsuits it’s facing for unethical sales practices. They wanted someone exactly like you to keep the place running smoothly as it’s sold off for parts.”

His face turned pale. For the first time, he didn’t have an answer.

Bruce was not Machiavellian by nature. His conniving behavior was more sad than it was evil. He was raised by strict parents who never told him he was good enough, which made him constantly strive for approval. And it worked. He ended up becoming CEO anyway — the title and prestige were irresistible. By doing so, he became the “proto-parent” whose love he sought so desperately. The tragedy was that, as CEO, his “children” would listen to him, but they would never love him.

The Striving Employee

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.

Counterintuitively, our early coaching work focused on teaching her to apply the brakes. Though accomplished at an early age, she was still an individual contributor and desperately wanted to move into management. It was clear that she would be promoted in due time, so the first task was just to instill patience.

“You know, while I can share my experiences and give you books to read, most of this you’ll simply have to learn by doing,” I told her.

“I understand,” she acknowledged. “I just want to be prepared when the time comes.”

“I appreciate that. But it’s like being a parent. You’ll never be fully prepared. I suggest you use your current position not to learn managerial skills, but to learn the intrapersonal intelligence you need to be successful.”

She listened intently.

“You have interpersonal intelligence in spades. You understand people and they like you because you treat them well. But you can develop more intrapersonal intelligence: knowing yourself.”

“I’d like to think I know myself. What else do I need to know?” she asked, curiously.

“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?”

She gazed off into the room, and said in an almost-whisper: “Yes, there was this one time…”

I nodded in encouragement.

She continued. “An executive from my last job. She wasn’t my manager, but took me under her wing, confided in me about an upcoming merger, and made me swear I wouldn’t tell my own boss.”

Her story sounded familiar, but I stayed reserved. “Why did you agree to keep that secret?”

“To be honest with you, the merger would open up a manager position in her department. I figured that if I kept her secret, it would curry favor with her enough to install me.”

“No wonder. So what happened?”

“My boss had heard rumors about the merger and asked me if I knew anything. I lied and said I hadn’t. I felt terrible, but I wanted that position so badly. Ironically, it never ended up being filled.”

“So how did this affect your relationship with your boss?”

“It didn’t.”

“It didn’t?”

“He just carried on as if nothing happened. I thought he never found out. But he eventually left and on his last day of work, he took a walk with me. He politely asked when I had heard about the merger, and I finally confessed I had lied. He said he had known, but didn’t begrudge me because I shouldn’t have been put in that position in the first place,” she explained solemnly.

“He forgave me, and even offered to continue to mentor me,” she continued. Then she shared a last bit of advice he gave her, which she said she’d never forget:

Integrity is everything. Jobs, managers, and even companies come and go, but your name stays with you forever.

“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.