If you have an excellent boss who has treated you well all year, you might be tempted to add them to your holiday gift list. That's not always a good idea, and it's a decision you should be very careful with.
"Tread carefully," Jo Bennett, a partner in the executive search firm Battalia Winston, told Monster.com. "It's not all that common and I think if you want to give a gift to your boss, you need to think about what's in it for you."
That sounds more dire than the situation actually is. There are scenarios where it's fine to give your boss a gift, but you need to do some work to figure out what's appropriate (or if just a thank-you card with a nice note is enough).
Learn the lay of the land
If you work at a large company, it's important to figure out what the policies and traditions are. If nobody in your department gives the boss a gift and it's not common at the company, in general, you probably shouldn't do it.
At some smaller companies, it's traditional to give the boss a group gift with everyone pitching in a small amount. If that's the case, then you should go along with the group and not do something on your own.
If giving an individual gift would not be out of the ordinary, it's fine to do so, but be careful. You want the gift to come off as sincere -- something you did because you want to say thanks, not an attempt to curry favor.
What should you give?
Generally, for an individual gift, you want to give something meaningful but not expensive. It can be as simple as a small gift card to someplace you know your boss enjoys going (maybe a favorite local coffee shop). Avoid clothing unless it's something like a T-shirt for your boss's favorite sports team.
Avoid anything too personal (you don't want to be the person who gives the boss underwear, no matter how well-intentioned) and don't spend more than $25. You should also be discreet in delivering the gift, as you don't want to show up your coworkers who chose not to get anything for the boss.
Be very careful
There's no work scenario where you have to give your boss a gift, unless you happen to draw her or him in a secret-Santa exchange or other type of gift swap. Before you even consider giving the boss anything outside of that scenario, you should make sure you're not sending an inappropriate message or doing something that nobody else does. You won't get in trouble for not getting the boss anything, so if you have any questions about propriety, don't.
That said, a heartfelt, carefully selected token gift can be very meaningful. Just make sure your efforts will be taken in the spirit they are being offered.
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