I haven't had any truly heinous bosses, I feel lucky about that, but I've had better and worse. And for the past 2 years, I've had Jerry, and I think it will be pretty much downhill from here. So what's so awesome about Jerry? Well, if I could describe it exactly, I could write a book and make kabillions. But I can't quite describe it, and besides, he is probably writing just such a book as I speak (the man has already written a dissertation-come-book and a certain-to-be-published novel in all the time he has leftover from his demanding job and two small kids) and would sue me for plagiarism. Because he's nice but he's not a fool.
First of all, Jerry is the most positive person on the planet without being too annoying. I mean, it's kind of annoying at first, but then he just wears you down with optimism until you cave and find yourself saying things like, "You're right, Jerry, it's actually a good thing that my house burned down and I lost everything I own because now I get to buy new shoes." He also heaps (hopefully not empty) praise on his employees, and yet it doesn't seem like flattery, you walk away thinking, "Hey, I might actually BE awesome. Or at least a little awesome. I think I might go read a whole book or run a whole mile. That's right."
Jerry is also really into the personal growth/leadership/corporate success crapola, but once again, one's eyes do not involuntarily roll up into one's head when he is pushing the stuff. For one thing, he's just so sincerely enthusiastic that to rain on his parade would make you pretty much the worst person in the world and no one wants to be the worst person in the world, except maybe Kim Jong Il, but he's just crazy and has bad hair. So I actually read--READ--The Five Dysfunctions of a Team (or was it 10?), which like almost all books of that type contained nothing really new or earth-shattering and yet you find it mysteriously inspiring. Kind of like Jerry.
Jerry also knows how to do both work and fun. Our team is the most productive team in our organization (stats don't lie, people!) We work, and he works. But he also spends time each day goofing off with us, leading brainstorms like "If our team was a TV show, who would play us?" and "What female stars are 'just OK'?" and teaching us the meaning of words like "hogly" (which means hot or ugly depending on the context. He claims Cameron Diaz is hogly, but I think he is on crack. Try Britney Spears, Jerry).
I think the key with Jerry is that he is incredibly socially skilled. He always knows how to strike the right balance. Like he is also extremely self-aware without being self-loathing. He's confident but not arrogant. He's funny but not inappropriate. He's short but not too short (OK he's too short. But he has a hot wife). He works hard and is devoted to his job, but he leaves on time. He's upbeat but no Pollyanna. He's encouraging but honest. I don't think you can really teach this kind of savvy, he would probably say you can. But I am not convinced, because despite his best efforts to induct me into the cult of optimism, I still loiter on its fringes.
Now Jerry is moving on to bigger and better things, thankfully within the organization. So maybe he'll remember me when he is huge (not tall, but huge).