For many workers, the holiday season means making a list, checking it twice—and trying to decide whether to put your boss on it.
Experts say it's a potential minefield because even though many workers may want—or feel the need—to give their boss a small token of appreciation, even the best intentions can quickly go wrong.
"It's a sensitive time of year," said Phyllis Davis, chief executive of the American Business Etiquette Trainers Association, based in southern Florida.
The correct protocol is that bosses should give their employees gifts but employees should not feel obligated to give a gift back, said Colleen Rickenbacher, a business etiquette consultant based in Dallas. Still, she said, it can be perfectly appropriate to give a gift to your boss, especially if you consider your boss a friend or you have worked together for a long time.
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But it pays to do a little research first, especially if you are new to the company. That's because if you give a gift and everyone else doesn't, you may look like you are trying to curry favor. And if you don't give a gift and everyone else does, you may be embarrassed.
Worse yet, if you do give a gift but it's inappropriate, that's the kind of faux pas that can follow you for years to come.
Worst-case in point: Rickenbacher recalled a time when a female employee sent flowers to the home of her male boss. It was meant as a kind gesture, but it left the wife of the boss wondering why flowers were being sent to their home by another woman.
"It was very innocent, but it turned into a huge fiasco," she said.
That's the kind of cautionary tale that makes human resources experts cringe—and advise their clients to stay on the conservative side when it comes to gifts.
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"Always err on the side of caution," said Sharlyn Lauby, a human resources consultant and author of the blog HR Bartender.
If you do decide to give your boss a gift, here are some tips:
Don't give anything too personal: Experts say a good rule of thumb is to avoid anything that touches the skin. That means no jewelry, no perfume, no clothing—and definitely no boxers or other intimate apparel.
"Unless you know the person really, really well, I would very much steer clear of gifts that really have a very personal tone," Lauby said.
Don't spend too much, or too little, money: A $2.99 ornament from the drugstore will likely come off as too cheap, but a $100 pen may seem awkwardly extravagant. Experts say the $10-to-$25 range is generally more appropriate for a midlevel manager.
Do consider food or gift cards: A consumable gift like cookies, candy or homemade bread is a nice way to show that you appreciate your boss without breaking the bank, Davis said. A coffee shop gift card or similar item also is practical and appropriate.
Do consider a group gift: If everyone goes in on one gift, Lauby said that can spread out the cost and also ensure that everyone in the department is on equal footing with the boss.
Don't generally give alcohol: Lauby once had a boss who was known to love champagne, so her team got together every holiday season and bought a case for the boss and his wife. That's fine if you know the person well, but in general etiquette experts say that these days some employers might frown on giving alcohol at work, and some bosses may see it as too personal a gift.
Do check on gift policies, especially if you are a vendor or freelancer: One year, Davis said she sent fancy cigar-shaped chocolates to clients at an oil company in Texas. To her dismay, the gifts got returned. Now, she recommends checking with the human resources department to see if there is a ban on gifts.
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"I always call first if I'm a vendor, to find out what their gift receiving policy is," she said.
Do consider books or magazine subscriptions—as long as they are appropriate: Reading material is usually a safe bet, especially if it relates to your field. But even such a seemingly mundane gift can turn inappropriate if you're not careful.
"You don't want to give your boss '50 Shades of Grey,' " Davis said.
Don't send a gift to a home address: The flowers fiasco is a case in point of why you want to make very clear that you aren't trying to be overly personal with your gift, Rickenbacher said. To avoid confusion, she recommends handing your boss a gift at the office or during your holiday party.
"Never send a boss a gift to their home," she said.