My husband was explaining to me that his administrative assistant seems truly stumped every year by what to get him for the holidays. Some years, she flat out asks him what he would want. When he told me this, I asked him whether he thought she even needed to get him a gift at all. His answer was "it's always nice to feel appreciated."
Many people struggle with whether to get their supervisor a holiday gift. I have been one of those people who has contemplated this dilemma many times. Like you, 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.
Over the years, I've given my editors something I knew they would enjoy --a fun mug with their favorite coffee, a container of homemade chocolate pretzels, a gift card to Starbucks with a note. Actually, 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 written short notes like: "Happy Holidays! Thanks for being a great editor!"
Another option is to pool with your colleagues to get one gift from everyone. Just don’t make it too personal or offensive. Miss Manners says this group present should be inexpensive (each person's contribution should be less than what the boss spent on them) and consumable, according to the boss's taste. A bottle of wine, a box of chocolates, or something similar.
Last holiday season, more than a quarter of workers said they planned to buy for the boss, according to a survey by staffing company Spherion. To get a boss' perspective, I asked a former editor of mine, Terence Shepherd, his thoughts about giving a supervisor a holiday gift. "It's really sweet," he said. But then, after a few minutes he added, "Of course, it's also risky. You have to know your boss well to know how it's going to be received. Also, don't expect anything in return." Terence says in prior years, he has given his boss a bottle of wine or champagne -- gifts he considers low risk. He also has received gifts he appreciated, including a scarf.
If you've got a particularly bad boss, I can't fathom buying him or her anything. However, you might have to contribute to the group gift to avoid landing yourself in the dog house.
Alison Green who writes the popular Ask a Manager blog, suggests looking closely at the culture of your workplace – and knowing your boss. A reasonable manager would never penalize someone, even subtly, for not giving her a gift at the holidays. On the other hand, you might not have a reasonable manager. Know your own situation, and proceed accordingly. (But know that etiquette is on your side if you choose not to give a gift.)
Also as a manager, you don't want to set the tone that gifts are expected. You might have to be outspoken about this if you truly don't want to receive gifts. In that case, as the employee, you can always give a nice card.
What are your thoughts on giving a boss a gift? Has it ever made you uncomfortable to give or receive a gift at work?