How important is a good boss?

I have had the opportunity to work for 10 companies. When I look back on it, it seems crazy. The first 22 years of my career was at one company – IBM. I grew up at IBM, started as a technical resource, switched into sales, sales management and general management. I learned most of what I know about taking good care of customers, leading a team, people management and living and working overseas, all thanks to IBM. I don’t regret a day of it, even though I don’t regret leaving. Since leaving IBM I have worked for Reuters, Serena Software (since acquired by MicroFocus), MicroFocus for a short period, Xerox, CSC (now called DXC), Earthport, Varius (a startup that ran out of funding after 6 months), Aternity and Zoovu. I have enjoyed a lot more than 10 bosses, given all that time at IBM.

Much is written about what a good boss is and is not. What I wonder sometimes is how much it matters.

I have learned plenty about myself in the 40 years since I had my first boss at IBM in New York City (it was August 3, 1981 and his name was Leo Tung). I know that I am more comfortable and more effective in a company culture that encourages teamwork, rather than one where people feel the need to look better than the person next to them and therefore develop sharp elbows in order to get ahead. I value teamwork as much as team leadership, and when I lead a team I don’t see that I need to be the smartest person in the room…I rarely am. I have had bosses who felt the need to be the smartest person the room. He or she just assumed that being the boss (especially being the CEO) meant knowing the answers and setting the direction such that others need to follow. I struggle with such leaders.

I have had bosses who were very very smart….one or two who were incredibly bright, such that I knew I could never compete with this level of intelligence. But why compete? I’m smart enough, and have enough expertise and experience to bring value.

I have quit over what I thought was a bad boss. I thought that having a good boss was too important and that I wouldn’t compromise my principles to work for a bad boss. Two companies I joined had great CEOs, but then the CEO changed over and the new boss was a jerk (in my opinion, at least). I ended up leaving, rather than carry on working for someone I did not enjoy working for.

Okay let’s choose an example. I had a boss at a software company who I grew to appreciate was incredibly bright, one of the smartest guys I have worked for (he happened to be a guy). He was almost always right, when it came to important decisions, he knew our technology, our customers and the operations of the firm – he made pretty much every decision of any import at the firm. He recruited me because he knew – intellectually, at least – that this won’t scale. If he has to make all the decisions and close all the big deals, then the company would never be as big as it could get. He struggled with delegation though. Furthermore, his style was truly a pain in the ass. He could be condescending at meetings, making fun of his staff, torturing them with questions and criticisms. I hate that. I don’t see why you would need to embarass someone in a meeting, even if you have concerns about their performance. He did this every week. He was often right with his criticism, and would attempt to put the staff member in question on a better course, but…

So – why do I pontificate about this? The question in my mind is how much it matters. If the company is wonderful in many other ways – great technology, great customers, etc – should I really be so unhappy that the boss is a self-described asshole (he admits this)? Should I just ‘get over it’ and try to contribute and enjoy the rest of the ride? Or should I throw away the opportunity to be part of a high growth organization because of this guy. Should i appreciate the value that comes with his experience, his understanding of the company and his tremendous intellect, and stop being a baby just because he’s a jerk, and just do what he tells me? Or is it just going to be torture to work for this guy, no matter how cool the company is?

I can’t decide.