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.
continue reading… Inc.