Things I Learned From Cool Bosses

If you are a nice person, being someone’s boss is one of the hardest things in the world.

Perhaps managing people is no easier when you’re an asshat. I'm not sure. But it sure looks easier if you're the type of person who can bark orders without flinching.

For years, I believed that some of my best traits (I’m gentle, empathetic and trusting) prevented me from being the kind of manager who can earn authority and respect. I’m best one-on-one, and I’d rather orchestrate a sugar-and-caffeine-fueled-brainstorm session than tell people what to do.

But this style, I’m finally here to tell you, makes an effective leader too.

I’m lucky because I’ve had some truly excellent bosses (and observed some bad ones) over the years, and now I get to steal the best techniques.

Like these:

1. Never sound fake. (Nobody buys boss-talk.) 

Example: When I sold black lights and gag gifts at the mall, my boss hated our customers. He never sugar-coated the fact that our clientele—usually teenagers or people who really thought fake poop was funny—were stupid. But he made his expectations clear: we had to sell stuff and be friendly so that we could get paid and create a nice environment to work. And so we did. (And when the district manager visited from Corporate and handed down impossible sales goals on things like cinnamon-flavored Spanish Fly--with a straight face!--we thought he was full of crap.)

Since then, I’ve learned that bosses, in their attempt to seem professional, will sometimes come at you with big words and office jargon that really mean: “I’m trying to mask the fact that I am giving you a stupid task, and I’m pretending that it’s for the good of the Company. Now do as you’re told.”

This is tricky because sometimes, as the boss, you have to rally your staff to do things that you secretly know are total bullshit. Like sell keychains with pictures of fat ladies on them (see above) or compensate for goofy office politics. I think it’s best to level with people, and explain why it is actually important that they do this stupid thing. Then thank them for being so great.

2. Always give your underlings credit. 

Example: One time when I worked in fundraising, I answered the phone. That was it. A foundation was on the other end, and even though I had never heard of them before, they had a big donation for us and they wanted to know where to mail it. Neat!

When I told my boss, Craig, about the call, he went around telling everyone that I had secured a big grant. That big check would have come with or without me, of course, but Craig built me up like that all the time. Now I get it, and I try to do it too. When my colleagues know what great work my staff is doing, they can give our time and efforts the courtesy and respect that’s due. That helps us do our jobs.

Sharing credit also prevents your underlings from secretly hating you for stealing their thunder. The boss always gets all the recognition for their team's work, and that's not fair.

3. Let your people get the hell out of there if they really need to. 

That same boss once made me take my meltdown outside. He recognized that a dozen personal problems were crowding out my ability to function like a human being. He cheerfully pulled me aside, told me to go out, sit with a coffee somewhere, and come back in a better mood. His kindness hit me as such a surprise, I sort of slinked out like a scolded dog. But I was so grateful for the chance to start my day over fresh, I came back motivated to kick ass.

Now, I know that when my employee is acting like she's fried, she probably has a legit reason and needs to go take a walk. That's okay.

4. Let them do what they’re good at. 

This one’s really important. If your work ethic is even halfway decent, then all you really want at work is to do a good job. My favorite bosses have removed red tape, sought approval and found money in the budget so I could get shit done. When it turned out I was better at doing one thing than another, they gave me more of what I was good at, so I could actually shine.

Now, I work with a brilliant designer who, when I can cut her loose, can blow your freaking mind. It's my job to make sure she doesn't get bogged down in too many things that prevent her from kicking ass.

5. Be a person that they can admire. 

This is a tough one, of course, but never stop trying!

Have you ever had one of those bosses who had a mysteriously busy schedule? Who was always dashing off to vague-sounding meetings, but never seemed to have any projects of his or her own? What do they do all day, while you're busting your butt? If they're doing something important, don't you think you should know about it?

The bosses I've admired most have been powerhouses who do great work and let me see it, so I can be in the loop and learn from their experience. They've let me in on the bigger picture. When you admire your boss, you don't just want to coast...you want to raise the bar to play at their level.

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Alright then! Get to work! Be honest! Be cool! And most of all, be nice! Your workers will thank you, and hopefully, be more awesome for you. That, Cool Boss, is your reward.