Many people struggle with whether to get their boss a holiday gift. I have been one of those people who has contemplated this dilemma many times. I don't want to look like a kiss up, but I also want to show a good boss that he or she makes my work life enjoyable.
I try to go with gifts that are a little personal, but not too personal. For many years, I had a manager I considered a friend. He and I spoke regularly about our kids, our jobs and our goals. He helped me to do the best work I was capable of by being supportive of work life balance. When it came time for the holidays, I knew he liked to cook and eat gourmet dishes so I gave him food-related gifts – unique cookbooks, homemade desserts, fun cooking tools. The gifts were always accompanied by a note.
When gift giving to a boss, I think the note is the important part. Some managers feel pressure from above -- all the time -- and appreciate someone on their staff acknowledging that they are good at their job. I've given small gifts like a fun mug with a handwritten short note like: "Happy Holidays! Thanks for being a great boss!" If you aren’t thrilled with your boss, you can tone it down and try to find one thing about him or her that you appreciate and acknowledge it in your holiday note.
Another option is to pool with your colleagues to get a group gift. The group present should be inexpensive but thoughtful. The easiest gifts are consumable or usable -- a food basket or tickets to a show or sporting event. If you have a particularly bad boss, you still might consider contributing to the group gift to avoid things getting awkward and appear a team player.
Gifts to a boss or co-worker are not mandatory. I think the key is looking closely at the culture of your workplace and reading your boss. A reasonable manager would never penalize someone, even subtly, for not giving him or her a gift at the holidays. On the other hand, you might not have a reasonable manager. Contemplate your own situation, and proceed accordingly. (But know that etiquette is on your side if you choose not to give a gift.)
Also, be careful about getting creative. One year, a manager I know received giant Buddha statue from his assistant. I guess she was trying to help him feel more zen. She insisted her boss display it. “Now I’m stuck with it seeing it every day and it irritates me,” the manager told me. “My advice is don’t give your boss anything he has to display. If you miss the mark, a nice thing turns into resentment.”
When he told me this, I asked him whether he thought his assistant even needed to get him a gift at all. His answer was "it's always nice to feel appreciated." However, I have asked other managers the same question and they have told me they don't want a gift and they don't plan to give their staff gifts.
What are your thoughts on giving a boss a gift? Has it ever made you uncomfortable to give or receive a gift at work? Is it more uncomfortable not to give a gift?