Prior to starting my own business I was something of a job-hopper. As a result, I have had more than the average number of bosses. Some were tyrants, and others were friends and mentors that I still stay in touch with.

I learned a lot from nearly every boss I've ever had, including one of the most important (and counterintuitive) traits of being a great boss.

And I learned that lesson via a Tale of Two Bosses.

Boss A:

Outside of work this boss could have been my best friend. He was funny, he was charming, he asked about my wife and kids. We had similar interests, beliefs, and outlooks on the world.

I instantly wanted to work for him, and the compensation package he offered was more than generous.

In fact, as a boss, he was more than generous about everything. He instituted a "results only work environment" (ROWE), which is tough for any company to manage, let alone a small, new, geographically dispersed company. This boss's default answer was always "yes". As a result, promises were made that could never have been kept.

This boss never yelled, he never raised his voice, he never tried to be a poor man's Steve Jobs. It was a different kind of tyranny all together.

It was the tyranny of "yes".

This boss wanted people to like him, and as a result the organization quickly devolved into a chaotic state that it never really recovered from. After 6 months there was a management exodus (including me), and a company based on a great idea struggled to regain its footing, and left a great deal of damage (for both customers and employees) in its wake.

All because of a pathological desire to be liked.

Boss B:

This boss and I would never have been friends outside of work. We were from very different backgrounds, viewed the world from dramatically different perspectives, and he was definitely not charming. He did not ask me about my wife and kids.

He did not ask about anyone's spouse and kids - including his own.

Unlike Boss A, I was not sure I wanted to work for Boss B. In the first four months of the job I tried desperately to find another opportunity, and submitted my resume to hundreds of employers, despite having been at my new job for just a few months.

Luckily for me, none of those potential employers ever called back.

Working for Boss B became one of the best career experiences I've ever had.

I learned more about sales, marketing, and entrepreneurship from this individual than I have ever learned from anyone else. He had an instinctual understanding of human nature, and was pretty obsessed about giving customers value for their money.

He did not care about being liked.

He cared deeply about being respected.

Not caring if people like you is not an excuse to be needlessly mean or inflict psychological damage on your employees. And, those behaviors will also prevent anyone from respecting you.

Bosses gain respect when they do what is necessary to get the job done. And doing what is needed doesn't require being cruel. Contrary to popular belief, the secret to Steve Job's success was not his willingness to publicly humiliate people who worked for him.

However, doing whatever it takes to get the job done often requires saying "no". Getting the job done often requires making unpopular decisions. Being a great boss means you are willing to be disliked.

In the end the Tyranny of Bluntness and Brutal Honesty is always better than the Tyranny of Yes.

(Author's note: My time with Boss A is not on my LinkedIn page, and I wish him the best. Wanting to be liked might not make you the best boss, but it doesn't make you the worst human being.)

Published on: Jun 1, 2016
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