The answers to most workplace-related holiday questions are pretty clear-cut. No, you probably shouldn’t wear a tacky Christmas sweater to a meeting with an important client. Yes, it’s probably a good idea to show up at the office holiday party if your boss is spending money on one in this economy. And of course, no, you shouldn’t drink too much eggnog at any workplace soiree. There may be no harder gaffe to live down than dancing on a table wearing reindeer ears with the intern from the 6th floor.

But what about gifts at work? Of all the holiday dilemmas you’ll face this year, this one may be more fraught with career landmines than any other. Is it wrong to buy gifts for some colleagues and not others? How do you cope with coworkers who decide everyone should pitch in $50 for a secret Santa swap? And when should you consider—if ever—buying a gift for the boss? Let’s take a look at each one.

Gifts for some coworkers and not others?

The answer to the first question is easiest: Yes, it’s OK. People make friends at work, where we spend an ever-increasing amount of our time. And while you might not want to flaunt the gift giving in front of everyone else, there’s nothing that says a small token of appreciation for the person who took time to mentor you through a tough decision or the friend who takes you out for drinks after every stressful deadline is a bad idea. It’s probably not necessary—a simple holiday thank you note would do. And keep in mind you may be contributing to the gift glut that invades many of our lives this time of year.  

Bowing out of Secret Santa?

Navigating all that gift-swapping is a tricky issue,though, especially when it involves co-workers with a grand secret Santa idea. Once someone on your team has gotten a bunch of people on board to swap gifts—forcing you to shop for some guy in marketing you’ve spoken to exactly twice all year—it’s hard to be the Grinch in cubicle 2. You could take time early in the holiday season and suggest that you each donate $20 to a charitable cause instead, which is something to which even your most holiday-crazed colleague can’t say no. But if it’s too late for that, buy the guy in marketing a bottle of wine, and think ahead for next year.

A gift for the boss?

To buy or not to buy a gift for the boss may seem like the most perplexing holiday dilemma, but it’s not. In most cases, you shouldn’t. No matter how hard you try not to, you run the risk of looking like you’re blatantly kissing up. Even if your manager has gone out of his or her way for you this year, a simple note of holiday thanks should suffice. If your team has already decided to go in on something together, it’s probably in your best interest to join, but you can still suggest that a charitable donation be made instead of a gift and that next year you consider sending a joint card instead.

Gifts for direct reports?

Buying presents for direct reports can be just as tricky as buying gifts for the boss, if for different reasons. Gifts can send the wrong signal and will be endlessly analyzed (my manager gave me a candle—does that mean my cubicle smells?), and worse, it will leave them feeling like they should buy you something in return. Your best bet? A hand-written holiday note of thanks for each person and a nice lunch out on your dime. The one exception? You should always buy a gift for an administrative assistant.

To help stop the gifting dilemmas at work, urge your team to put their efforts toward a charitable contribution made on everyone’s behalf instead of individual gift swaps. People already have enough to do—and enough distractions from their work—as they try to sort out what to buy their fathers-in-law, their kids’ teachers, and how to keep everyone in their family happy through the emotional roller coaster that is the holidays. This time of year, they shouldn’t need to worry about what to buy the human resources manager they had the luck of drawing this year for Secret Santa. Call me Scrooge, I guess. But I think it’s leaders’ jobs to make life easier for the people who work for them, and to model what this time of year is really all about.

Jena McGregor is the Post Leadership blogger for the Washington Post.

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