Biggest Regret, Failure and Learning Experience

I don’t believe anyone can lead a life without regrets.  Though it’d be nice, if you encounter someone who can lay claim to that then he is a person who can’t empathize and lives a very self-centered life.  (And now I regret casting that stone…)

That said, my biggest regret (caveat: in the workplace) was one of the first true tests I had as a manager.  A test I failed.

One of the guys on our team came to me seeking career advice.  He didn’t love his role or my boss and wanted my advice on whether he should stick with it or pursue a riskier venture, but one that he really enjoyed.

A quick note on him: I loved working with him.  He was intelligent, very creative and funny and was good at what he was tasked with doing.  The risky venture?  His wife was an actress on a popular cable show and he’d been dabbling in writing episodes for her show.

He prefaced our discussion by saying that he respected my input, ability to shoot-straight and trusted that I could give him sound advice from a viewpoint that wasn’t his manager.  This should have been such a perfect lead-in that I couldn’t have possibly failed.

Rather than tell him what I truly believed (and still do), I spoke from a very selfish point of view.  I liked working with him, I needed him on the team and he provided a necessarily role on the team that had nothing to do with output.  I talked about the opportunity, the team we had and the awards for which we were nominated.

Nothing I said was a misrepresentation, but it was coming from my best interest and not his.

The moral?

You can’t be a leader (and thus a successful manager) if you can’t put your teammates needs in front of your own.  Respect them enough to be transparent and tell them the truth.  And, most importantly, do both of you a favor.  Encourage your teammate to do what s/he enjoys.  It’s hard to be successful (though not impossible) if you can’t put your heart into your job.

And how many times does one really get the chance to write for a popular television show?

Fortunately, he saw that I was full of shit and left anyway.

While I regret the poor ‘advice’ (used rather loosely) I gave, I’m grateful for the lesson that’s stuck with me for the past decade.

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