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Do I get my boss a gift? I have run across this question more than any other when it comes to holiday-time. The quick answer is that it varies based on the environment you are in and if you are a gift-giver or not – and the “real answer” is YES.

Gifting at Work

I would recommend erring on the safe side and having a gift ready to go, regardless of the environment you are in. Then it is up to you if you deliver it or not and you are not left empty-handed if your boss steps up to the plate. With that in mind, here is some guidance, learned the hard way, of course.

  • Your boss should be getting you a little something for the holidays as a thank you for working so hard this year, gift. If your boss manages 20 people, don’t expect anything huge, just a small token. I have personally received gifts as small as candy to as fabulous as crystal glasses, and everything in between.
  • Ask people who have been at the company for some time, that you trust, what the gift-giving culture is. In some places, giving your boss a gift is taboo and frowned upon (yep, I stepped into that puddle before), and it’s important to know that before the gifting begins. That doesn’t mean that you shouldn’t gift, particularly if you want to, but how you deliver and present the gift will be vastly different. You should be more discreet about it and not tell the world what you are up to.
  • Whether you decide to get your boss a gift or not, know that you will be judged for that either way. This is a lose-lose situation. Either your boss will be miffed that you didn’t show them some kind of acknowledgement, or your coworkers will be annoyed. So ultimately, the choice of which “losing situation” is better, is one you have to personally make.
  • There is a line that I would recommend drawing, as I have embarrassingly crossed it a few times. If you work in the “normal world,” excluding finance and the like, spending $100 on your boss’ gift is well beyond extravagant. Depending upon your level in the organization, you should aim to spend no more than $50 (and that’s high) and the gift should be personable and work-appropriate.
  • Stay away from the following, regardless: clothing or any kind (pajamas, shoes, slippers, etc.); romantic-gifts; blenders and the like; items that are banned from your workplace (knives, guns, etc.); essentially, anything that would not give in the presence of your grandma.  Booze is a tricky one – I personally am not a fan of it, but if you know that your boss loves a particular wine or spirit, then it would be appropriate. A six-pack of beer, not appropriate.

And if you are a boss of any kind, suck it up and get your team gifts – even if it is a small token of thanks. THANK THEM.

What’s the best gift you’ve gotten or given for your boss?