5 Examples of Controversial Leaders (and Why the Best Leaders Are Often Polarizing)

Jayson DeMers
4 min readJul 17, 2020


Photo by Hermes Rivera on Unsplash

We like to fantasize about great leaders being idealistic in every dimension; they’re strong, smart, noble, calm, easy to get along with and almost anyone who meets them can see plainly that they’re cut out to be a great leader.

But in reality, many of the greatest leaders we praise and envy are controversial figures, conjuring as much ire and resentment as loyalty and admiration. They’re polarizing, which is somewhat surprising — until you realize that this polarization could be part of what made them successful in the first place.

Let’s take a look at five examples of controversial leaders and how their polarizing practices helped to make them a success:

1. Steve Jobs.

There are countless examples of Steve Jobs’s dismissive, arrogant and condescending behavior, due in part to his attitude of not caring what other people thought. He would ask flabbergasting personal questions in interviews to intentionally put prospective employees under stress, he would fire people without warning and had a zero tolerance policy for mistakes and failure.

Though some of these practices led to his getting fired from his own company, he returned with the same culture to help build Apple into the tech powerhouse it is today.

2. Jeff Bezos.

The culture Jeff Bezos has created at Amazon has been described by a human resource director there as “purposeful Darwinism,” a ruthless policy that demands high performance, lest you face serious consequences. Long hours are expected, mistakes aren’t especially well-tolerated, and anything that interferes with your productivity — including personal issues — will put you in a “performance improvement plan,” a euphemism indicating you’re in danger of being fired.

Nevertheless, highly competitive and highly productive people have no problem fitting into the culture and Amazon has had a long history of success and innovation because of it.

3. Larry Ellison.

One of the richest people in the world, Oracle founder Larry Ellison had a knack for finding amazing talent, especially considering most Oracle executives have gone on to create or manage some of the biggest names in the modern tech industry. But his style irritated a lot of people.

Ellison has been described as a highly competitive egomaniac, using other people’s fear and greed as motivational tools and encouraging internal competition whenever he got a chance.

4. Andy Grove.

Former CEO of Intel Andy Grove was kinder than some of the other examples on this list, and was named Man of the Year in 1997. Still, he had a controversial leadership style, marked by his quick temper. He would berate people for offenses as small as showing up late for work, and held all his employees to ridiculously high standards.

He constantly pushed for more, and looked to the future and as a result, he helped build Intel into a juggernaut.

5. Travis Kalanick.

Travis Kalanick has caught significant and justified criticism for encouraging an environment of sexism and ruthlessness that nearly caused Uber to crumble after its incredible pace of growth. Still, Kalanick’s boldness, brashness and competitiveness were important ingredients in influencing the company’s rapid expansion to a $70 billion empire.

During its early years, Kalanick pushed his employees and expanded his company relentlessly and it’s only after public criticism that he was forced to step down. Sexism can’t be tolerated in any work culture, but competitiveness and ruthlessness are valuable tools.

Why the Best Leaders Are Polarizing

So why are some of the most successful leaders so polarizing? These are just five of the reasons illustrated by the examples above:

· Specific demands. Polarizing leaders tend to have very specific demands; they have a singular, detailed vision and are fiercely committed to achieving it. Accordingly, they’re inflexible and demanding, which can filter out certain types of people who might not fit in with a certain kind of company culture.

· Uniqueness. Leaders that push and bend the rules also tend to create controversy, but following all the “right” rules and doing only what’s expected leads entrepreneurs to complacency. The uniqueness factor makes controversial entrepreneurs break the mold, distinguish themselves from the competition and make a bigger mark on their respective industry.

· High expectations. Entrepreneurs often become polarizing because of their high expectations as well; they have little to no tolerance for failure and demand peak performances from their employees. Accordingly, they tend to drive more innovation and get more done than their competitors.

· Passion and loyalty. Fiery, controversial entrepreneurs tend to be more passionate and charismatic, inspiring more loyalty from the team members who stay — even if some of the other team members flee.

You shouldn’t act like a jerk for the sake of acting like a jerk, nor should you intentionally make decisions to inspire resentment, but there are benefits to staying true to your vision and making high demands of your employees — even if it means ruffling feathers.

Keep this in mind when developing your own leadership style and you, too, could become a polarizing, yet influential leader.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!



Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!