How Bill Gates was like Michael Jordan while running Microsoft

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Bill Gates helped build Microsoft into one of the world’s most valuable companies. But between the hard work it took to get the company off the ground and the pressure to succeed against fierce competition, the billionaire Microsoft co-founder wasn’t always such a nice guy to his employees.

Gates, much like fellow tech icon Steve Jobs of Apple, was known to push employees to the limit during his tenure atop Microsoft.

In a recent interview on the “Armchair Expert” podcast, Gates admits that his own intense work ethic as the CEO of Microsoft often made him extremely tough on any of his employees’ mistakes.

“I certainly wasn’t a sweetheart when I ran Microsoft,” Gates tells the podcast host, Dax Shepard, in the interview. 

In fact, while discussing his sometimes harsh demeanor as Microsoft’s CEO, Gates even agrees with Shepard’s comparison of Gates to Michael Jordan. The NBA Hall-of-Famer’s famously intense work ethic is often credited as one of the reasons why Jordan is considered possibly the greatest basketball player ever. 

Jordan’s intense drive made him extremely tough on himself as well as on his teammates, whom he expected to work just as hard as he did to strive for greatness. That type of intensity has parallels in the business world, as well, with countless stories surfacing about founders and CEOs with seemingly impossible standards.

During the “Armchair Podcast” interview, Shepard brings up ESPN’s “The Last Dance,” the popular docuseries about Jordan and the Chicago Bulls dynasty that aired in April. Gates calls the series “fantastic.” He also agrees with Shepard’s assertion that there are similarities between Gates’ leadership style in Microsoft’s early days and the famously harsh demeanors of the NBA Hall-of-Famer and the Apple co-founder Jobs.

One aspect of Jordan’s personality as a teammate that Gates says “I think you can say for Steve or myself” has to do with the fact that their high expectations for their colleagues and employees were only extensions of their own incredibly high standards for themselves.

“I never asked [Microsoft employees] to work any harder, or be tougher on their mistakes, than I was on myself,” Gates says, comparing himself to someone like Jordan or Jobs. “It doesn’t completely forgive it, but at least it shows where you’re coming from, that at least you’re projecting your own values and trying to get everyone to be hardcore like you are.”

If any employees didn’t feel they could thrive in that type of intense environment, Gates adds, no one forced them to stay at Microsoft — just as Jordan’s teammates on the Bulls could have sought a trade or left for another NBA team, he says.

As the 1993 Gates biography “Hard Drive: Bill Gates and the Making of the Microsoft Empire” previously recounted, Gates had a notorious temper during the early days of Microsoft, which he launched with Paul Allen in 1975. Gates often sent “critical and sarcastic” emails, which employees referred to as “flame mail,” to workers in the middle of the night criticizing their work.

Some programmers would receive late-night notes from Gates informing them that their work contained “‘the stupidest piece of code ever written,'” and many of Gates’ Microsoft employees described working under the then-CEO as “demanding” and “intense,” according to the book.

For his part, Gates fully admits that he was a harsh boss. “When I was at Microsoft, I was tough on people I worked with,” Gates wrote in 2019. “Some of it helped us be successful, but I’m sure some of it was over the top.”

In the podcast interview, Gates says he definitely tried to push his employees as hard as he pushed himself.

“If you push yourself super, super hard, and you’re so tough on [yourself] when you made a mistake … you definitely project that onto other people, particularly if you’re trying to move at full speed,” he says, noting that in the early days of Microsoft, every moment was crucial in out-maneuvering the company’s many tech competitors.

What’s more, Gates says he also tried to make sure his employees still knew that he respected their work, and he wanted them to know “‘the reason you’re here is because you’re amazing, so don’t get confused when we’re being kind of tough,'” he says. “‘We’re a team and we’re in this together.'”

“Every once in a while, we may have been tougher than we needed to be,” Gates admits in the interview, though he adds that he “was not as tough as Steve [Jobs].” 

And much like Jordan, who some former teammates have described the Hall-of-Famer as a “jerk” while also admitting that his intensity helped make his teammates better on their way to winning championships, some former Microsoft employees have said that Gates’ famous work ethic and harsh demeanor helped motivate them and that they also admired his ability to put aside his ego and admit when he was wrong. 

Now that he is retired from Microsoft (Gates stepped down as CEO in 2000 and he left the company’s board in March 2020), Gates says he has different ideas about the best ways to motivate people.

“Now that I’m older, I do think I’m more subtle about motivating people without having to push as hard,” says Gates, who now spends most of his time working with the Bill & Melinda Gates Foundation. 

He goes on to note that it helps him to have more going on in his personal life, including his wife of 26 years, Melinda, and their three children. When Gates founded Microsoft, he was still a young man and he admits that he had little else going on in his life outside of building the company. 

“I was in my 20’s [when Microsoft launched], so I do think I’m a little better at that,” he says.

Check out: Americans spend over $5,000 a year on groceries—save hundreds at supermarkets with these cards

Don’t miss:

Michael Jordan was a ‘jerk,’ say teammates—but it helped them win championships

Bill Gates was an angry, difficult boss in early Microsoft days—here’s why employees still liked him



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