Got a question for Doree? Email firstname.lastname@example.org.
How do you acknowledge a boss's birthday?
Oh, this is such a tricky and fraught question! It's so tough to know how anyone, much less a boss, is going to respond to any acknowledgment of their birthday (especially as people get older). In general, I am not really down with the whole birthday celebration at work thing — you know, when everyone gathers in a conference room for a fake meeting and then you have to stand around awkwardly with frosting on your face for 20 minutes — but I think a non-surprise, non-cupcake acknowledgment is potentially appropriate, depending on your relationship with your boss.
If you have a professionally close relationship with your boss — you consider her a mentor, perhaps — then it's okay to get her maybe a small box of chocolates, or some homemade chocolate chip cookies. A small, tasteful bouquet of flowers is also fine, though it can seem slightly weird if you're a guy giving them to a female boss. I wouldn't get too personal or expensive. Definitely not clothes or jewelry, and definitely not anything that could be perceived (by your boss or others) as an attempt to curry special favor (aka ass-kissing).
I guess I'm not really comfortable yet calling myself a boss, because, I don't know, it's scary? (Trying to own it! Give me a few weeks!) But, I am now in a position where I supervise people, and it was recently my birthday, and a few of my co-workers got me a box of macarons because they know I am obsessed with macarons. I was very touched! It seemed like an entirely appropriate gift, and I was not subject to any awkward conference-room shenanigans.
But maybe the most signficant potential boss-birthday pitfall is, you don't really ever know how your boss feels about his or her birthday. So sometimes a quiet "happy birthday, boss" is all that you really need.