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

Many of us have a very unrealistic picture of what a good leader looks like: Slow to criticize, generous with praise, doesn't shout, seeks harmony and prefers agreement over disagreement.

This type of leader certainly exists, but after 10 years of researching and interviewing some of the world's most successful people — from founders and executives to athletes and entertainers — I've found that the majority have one thing in common: a willingness to put up with clashes of interest in their company for the sake of change and progress.

Take Microsoft co-founder Bill Gates: In addition to his groundbreaking innovations, the billionaire is best-known today as a kind, compassionate and soft-spoken philanthropist. But decades ago, a much younger Gates earned a reputation as the office bully.

According to James Wallace and Jim Erickson, authors of the 1993 Gates biography "Hard Drive: Bill Gates and the Making of the Microsoft Empire," Gates was notorious for sending "critical and sarcastic" emails — often referred to as "flame mail" — to his employees in the middle of the night.

More than one "unlucky programmer received an email at 2:00 a.m. that began, 'This is the stupidest piece of code ever written,'" the book recalls. Former Microsoft employees described the office as a very confrontational environment, with Gates being "demanding" and the work "intense."

Another anecdote comes from Joel Spolsky, founder of Stack Exchange and a former program manager assigned to Microsoft's Excel product line. In a 2006 blog post, Spolsky writes about his first in-person product spec review with Gates. In addition to several other managers, there was also a person "whose whole job during the meeting was to keep an accurate count of how many times Bill said the F word."

"The lower the f***-count, the better," Spolsky recalls. As the meeting progressed, the questions Gates directed at him "got harder and more detailed."

Of course, these anecdotes about Gates' notorious temper only tell one side of the story. Gates knew better than any other entrepreneur how to inspire and motivate his staff to achieve a shared goal, while also giving them leeway to develop creatively.

After all, as Spolsky later learned from his colleagues: "Bill doesn't really want to review your spec, he just wants to make sure you've got it under control. His standard M.O. is to ask harder and harder questions until you admit that you don't know, and then he can yell at you for being unprepared."

In fact, Gates' employees expected to be challenged, and they expected to be able to challenge Gates. "A lot of people don't like their jobs because they don't get any feedback," Scott MacGregor, who Gates hired from Xerox, told Wallace and Erickson.

This was never an issue at Microsoft. "You always knew what Bill thought about what you were doing," MacGregor continued. "The goal, the motivational force for a lot of programmers, was to get Bill to like their product."

Moreover, Gates wasn't afraid to change his mind if someone made a convincing argument. It was a quality that Steve Wood, one of Microsoft's first programmers, came to admire.

"He can be extremely vocal and persuasive in arguing one side of an issue, and a day or two later he will say he was wrong," Wood told Wallace and Erickson. "There aren't many people who have the drive, intensity and entrepreneurial qualities to be that successful who also have the ability to put their ego aside. That's a rare trait."

The billionaire has since learned that there are limits as to how hard managers should push their employees.

"Growing up, if I thought my parents were being unfair, I could be pretty harsh with them," Gates acknowledged in the 2019 annual letter he published with his wife, Melinda. "When I was at Microsoft, I was tough on people I worked with. Some of it helped us be successful, but I'm sure some of it was over the top."

Still, the pioneering spirit and inspiring atmosphere at Microsoft attracted many intelligent and ambitious young people to the company. "[Gates'] confrontational style of management helped Microsoft maintain its edge — its mental toughness," Wallace and Erickson note in their book. "It made those who worked for him think things through."

Gates' leadership transformation is a perfect reminder that those in positions of authority are respected only if they have a track record of risking confrontation, if and as necessary, for the sake of doing what needs to be done.

That doesn't always mean getting angry and tough, but it does mean prioritizing the enforcement of legitimate goals and expectations. If it can be done in a gentle way, good for you. But every great manager knows, as Gates did, that there will be times where they need to voice criticism unequivocally.

Rainer Zitelmann is an entrepreneur, investor, leadership researcher and author of 23 books, including "Dare to Be Different and Grow Rich: Secrets of Self-Made People" and "The Wealth Elite: A Groundbreaking Study of the Psychology of the Super Rich." He holds doctorates in History and Sociology. Previously, Rainer worked as a historian at the Freie Universität Berlin.

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