Last week, I asked about the worst boss you’ve ever had, but this week, I’d like to ask who your best boss was. Luckily, I’ve had way more awesome bosses than rotten ones, so I’ll just tell you about one who really sticks out in my head. His name was John.

I worked for John at my first job out of college as a market researcher. Before working for John, I’d had two other bosses at the company who followed all the rules. Every. Painstaking. One. I never left the office to meet with clients because junior associates were like children who should be seen at their desks but not heard. 

When I moved over to John’s team, it was like starting an entirely new job. First of all, John didn’t follow any of the rules. Because he was good at what he did, he got away with it and did whatever he wanted. He started inviting me along to client meetings so that I could “contribute” (which was really flattering and intimidating at the same time). When he traveled for fun gigs that involved eating at Wolfgang Puck restaurants in the name of research, I got to go, too. 

In the afternoons, he’d sit working in his office while listening to jazz recordings. And if you walked in to talk to him, he’d get up to make you an espresso. Sometimes if you passed by him in the hall, he’d say, “There she is!” as if you were just the person he’d been looking for all day. 

On my last day, he sent me an email that said, “I’d wish you good luck, but you won’t need it.” How cool is that?!

Who is your favorite boss? What are they like?