Be careful when taking inspiration from tech gurus. Success isn’t the only metric to good leadership.
When Walter Isaacson’s biography of Steve Jobs hit the shelves, it became an instant bestseller. Suddenly, every entrepreneur thought the key to success was emulating Jobs’ quirks — from his obsessive attention to detail to his reputation for being, let’s say, “difficult.” It was as if wearing black turtlenecks and being hard on people were the secrets to creating the next Apple.
My wife once worked for a small company whose founder idolized Jobs. He treated the biography like a step-by-step guide to leadership. Every new office policy seemed to trace back to a chapter he’d just read. He mimicked Jobs’ secretive management style, micromanaged everything, and set goals so unrealistic they felt more like dares than actual direction.
Convinced that the path to success lay in Jobs’ tactics, he ignored the realities of his own business. To no one’s surprise, within a couple of months, the team was burned out. By the end of the year, the original team of 15 had all but vanished, replaced by new hires who didn’t last long either. What was once a promising fashion company fell apart because of poor management and unrealistic expectations.
Jobs isn’t the only tech guru to gain a cult following. Leaders like Jeff Bezos and Elon Musk are also treated as icons, despite their questionable work ethics. Musk’s infamous “hardcore” work culture demands long hours and weekend shifts, framing exhaustion as a badge of honor. Bezos’ obsession with efficiency has reportedly led to warehouse employees having their bathroom breaks timed.
Harsh methods may deliver short-term results, but they often leave destruction in their wake. For most companies, this isn’t sustainable. The best work is achieved in environments where people are allowed to thrive, not just survive.
The dark side of gurus
It’s easy to admire qualities like “vision,” “drive,” and “grit” in leaders. But when taken to extremes, these traits can lead to burnout, toxic work environments, and even criminal behavior.
Vision can morph into delusion. Drive can turn into obsession. And grit can harden into stubbornness that blinds you to reality.
History is full of leaders who were celebrated at their peak, only for their methods to fall apart spectacularly. Their stories serve as cautionary tales of what happens when ambition goes unchecked.
Elizabeth Holmes (Theranos)
She idolized Steve Jobs to the point of wearing black turtlenecks. Her obsession with secrecy and success led her to fabricate test results and commit massive fraud, landing her in prison and destroying what was once a $9 billion company.
You can watch her story in the series The Dropout or read the book Bad Blood by John Carreyrou.
Travis Kalanick (Uber)
Aggressive and uncompromising, Kalanick’s leadership style drove Uber to global dominance. However it also created a toxic workplace rife with harassment scandals and unethical practices. The board eventually forced him out to save the company’s reputation.
The TV series Super Pumped: The Battle for Uber dramatizes his rise and fall, based on the book Super Pumped by Mike Isaac.
Adam Neumann (WeWork)
Neumann’s charisma and “visionary” ideas initially made WeWork a startup darling. But reckless spending and bizarre behavior, like throwing lavish parties and funding personal projects with company money, brought WeWork to the brink of collapse.
You can dive deeper into his story in the show WeCrashed or read the book The Cult of We by Eliot Brown and Maureen Farrell.
Sam Bankman-Fried (FTX)
Once hailed as a crypto genius and a leader of the effective altruism movement, Bankman-Fried’s risk-taking and unethical use of customer funds led to FTX’s catastrophic collapse. He now faces potential decades-long prison sentences for fraud.
His rise and fall is chronicled in the book Going Infinite by Michael Lewis.
You don’t have to be an jerk to be a leader
The myth of the tough, authoritarian leader has been celebrated for centuries, from Julius Caesar to Logan Roy in Succession. Fear-based tactics, relentless pressure, and hyper-competitiveness are often seen as the price of greatness. But in reality, leadership rooted in collaboration and trust consistently delivers better results — for both the business and the people driving it.
Research shows that teams led by empathetic leaders are more engaged, innovative, and productive. People work best when they feel supported, not scared. This is especially true in creative industries, where innovation requires taking risks and thinking outside the box, things employees won’t do if they’re afraid of failure or retribution.
That doesn’t mean leadership is all hand-holding and sugarcoated feedback. Tough decisions are inevitable, and accountability matters. But great leaders balance accountability and high standards with empathy. They create environments where people feel safe to share ideas and challenge assumptions.
Microsoft’s transformation under Satya Nadella is an example of an alternative leadership style. He prioritized collaboration, breaking down silos and promoting teamwork. This cultural shift not only revitalized the company but also drove innovation, leading to products like Microsoft Teams and Azure Cloud.
Even in high-pressure industries, this balance is possible. Empathetic leadership taps into intrinsic motivation, making employees feel valued and respected. Fear-based environments might deliver short-term results but often result in burnout, turnover, and stagnation.
A better way to leadership
If you want to be a leader, you don’t have to choose between results and empathy. The best leaders understand that people are not just resources to exploit.
There’s no need to make others miserable (or make yourself miserable) to achieve greatness. Just because it worked for Jobs, Musk, or Bezos doesn’t mean it’s the only way.
Great leaders achieve exceptional outcomes by trusting people. Billy Beane, as general manager of the Oakland A’s, didn’t demand perfection through fear but encouraged his staff to challenge norms. He revolutionized baseball with his leadership style. (if you haven’t watched it, you should, it’s excellent).
The most impactful leaders leave people better than they found them.
Great leaders motivate rather than intimidate. They challenge without dehumanizing. And they understand that success isn’t just measured by profits or headlines but by the lasting impact on the people who helped achieve it.
Last I heard about my wife’s ex-boss, his team was down to just him and two other employees. Don’t follow his example. Leadership isn’t about mimicking gurus — it’s about finding your own approach, one that inspires and fosters a culture where people can thrive. Write your own playbook.
Looking for leadership role models in the wrong places was originally published in UX Planet on Medium, where people are continuing the conversation by highlighting and responding to this story.