former bosses

I have had a lot of bosses over the years.  All different kinds. Men. Women. Younger than I. Older than I. Smarter than I. Less Smart than I. Moronic.  Nice. Not nice. Political. Apolitical.  Capable.  Clueless.

Many I have stayed in touch with.  And a couple I have since become friends with.  But there are those I still cringe even to think about.

Heading the list of those I would never ever befriend are:

Don.

I worked for him a trillion years ago in Chicago at Blue Cross Blue Shield.  He was more Michael Scott than Michael Scott was.  He had a list of what he hoped to accomplish during his first 100 days.  He made a big deal about telling us, his underlings, all about it.  He tried to impose a business-like atmosphere into a world where claim adjusters were allowed to come to work in fluffy slippers.  He didn’t last long.

Bill.

He held a senior position at a major media company, until he was eventually fired.  Bill was incapable of making a decision.  I once saw his notes from a speech he was giving using a teleprompter.  On his notes he had written throughout, R, C, L, R, C, L.  I later learned these were notations as to where is eyes should be when he presented.  I mean really.  He’s overseeing $1 billion in sales and needs assistance as to where to place his eyes when talking to others.

But over the years, I’ve become friends with two of my former bosses.

Gail.

I worked for her at Gillette in 1981 after graduating from business school.  I consider this my first real job, and Gail, my first real boss.  All those who preceded her were amateurs by comparison. Gail was totally invested in my future.  Concerned. Bright. Protective. Creative. And fun.  But more than anyone before or since, she taught me how to be a good writer.  Gail and I were not friends until three years ago when we reconnected via LinkedIn.  It now feels as if we’ve been friends since 1981, not 2011.

Caroline.

I reported to her at CNBC in 1990.  She’s scary smart. Intense, and intimidating. But she’s also warm, and thoughtful.  We became friends when we worked together.  We even went skiing at Vail with a small group, including Eric (Alexander's soon to-be dad). But while I was on pregnancy leave, Caroline eliminated my job. We didn’t speak until I bumped into her at a party on Cape Cod 15 years later.  I ended up working for her on two different assignments at the company she was heading. Today we meet for lunch. The intelligence and focus that make her successful in business also make her a good friend. 

Collectively I’ve learned a lot from the people I’ve worked for.  I’ve learned what not to do as well as what to do. But when a former boss becomes a current friend, well, that’s pretty special.