Holiday gifts for the boss: Yay or nay?

From career advisors to the reigning queen of etiquette, Emily Post herself, most experts agree gifts for a workplace superior are an unwelcome addition to the holiday festivities. But as with most gift-giving guidelines, this one varies significantly from one workplace to another and depends on your relationship with the intended recipient.

A gift of thanks is the best kind

As career advice blogger Penelope Trunk puts it, "everyone wants a gift that tells them they are special." And in the case of our employers, that gift ought to be a simple, hand-written thank you note. Gifts of tangible value, on the other hand, may say, "I'm trying to win favor" to both bosses and coworkers. As she puts it, giving gratitude will make you feel far more warm and fuzzy (my words, not hers) than giving stuff.

That said, some of us still feel compelled to spread the holiday cheer through gifts. ConsumerSearch editor-in-chief Christine Frietchen explained to the Pittsburgh Post-Gazette that there are a few situations when gift-giving may be appropriate Here some factors to consider:

• Office culture. Offices that hang decorations and partake in a Secret Santa exchange are obviously more open to holiday celebration. On the other hand, in more corporate offices, the show of holiday cheer might just make your boss uncomfortable.
• Your field. Some offices are more accustomed to giving and receiving gifts, like folks in sales, marketing, or advertising, for example.
• The relationship. You and your boss may actually be out-of-office pals (kudos to you!), or perhaps your manager has been especially understanding of a difficult personal situation. If you want to give your boss a gift as a friend, present it outside of the office (same goes for co-workers, some experts say). If you couldn't imagine running into your boss after hours, though, you probably aren't close enough to give a gift.

Split the difference: Tactful ways to give

There are ways to give your boss a gift that doesn't cross the line. Here are a few expert recommendations we think would go over well almost anywhere:

• Pool your resources. A gift from the whole office (or your department and others at your level of the corporate ladder) will look less like brown-nosing on one person's part, say Emily Post and CBS. Avoid mandating dollar amounts, though. Make a conservative suggestion, while allowing folks to give whatever they deem appropriate. It'll result in a nicer gift that's better for everyone's budgets.
• Wrap-up something homemade. Martha Stewart Living suggests giving a tin of homemade cookies or other treats. Just do so in private, and make sure you're aware of your boss's diet restrictions or allergies.
• Give a thoughtful gift card. Keep the dollar amount relatively low, but the gift card personal. By considering your boss's tastes, hobbies, and preferences in selecting a card, you can demonstrate that the gift is more than just money, while also refraining from getting anything too specific to your own taste.
• Include everyone. Employers and employees alike will appreciate a tray full of goodies or individually wrapped treats. When including everyone, it's more appropriate to include your boss. Just ensure everyone's gifts are of equal value.

What and when not to give

Despite the best of intentions, sometimes gift-giving simply isn't appropriate. We outline the gifts (and gift-giving scenarios) that are better left un-given:

• Your office has a gift policy. Quintessential Careers points out that larger corporations may have a stated policy on gifts. Check with HR before giving to your boss if you suspect this may be the case. If so, don't give (or stay within the stated limits). Disobeying the rules could be bad for you and your manager.
• Don't give to prove a point. Only give when it truly comes from the heart; not because you hope to receive something in return.
• Skip overly personal gifts. Bath and body products, for example, are very personal and near impossible to choose for someone you don't know very well. If you're certain your boss would love an at-home spa day, give a gift card to a bath product store instead.
• Keep things tasteful. Don't give alcohol or gag gifts. Unless it's a white elephant gift exchange, gifts intended to be silly can come across all wrong, and alcohol sends the wrong message, too.