Leah-Anne Thompson

Is it a good idea to give the boss a holiday gift?

Holiday gift exchanges at work can be veritable political minefields, and few are trickier to navigate than the question of "gifting up" -- giving the boss a gift.

Some employers may expect gifts from their employees. Others may disdain them. And when it comes to how the boss treats the employees, some employers land squarely on the "nice" list and others on the "naughty."

Sherri Athay, author of “Present Perfect: Unforgettable Gifts for Every Occasion,” generally advises employees not to get the boss a present. However, she says that small gifts, such as baked goods, are appropriate.

April Masini, who pens the online advice column, AskApril.com, cautions that it’s important to understand your workplace’s culture.

“If you're not sure, ask around. Some companies are very easygoing about gifting up and anything goes. Others frown on it. And still others expect it,” Masini told TODAY Money. "This kind of etiquette isn't going to be in a human resources handout. Use your social skills to figure out your company's unwritten rules.” 

While the experts say skip it, or at least proceed with caution, employees also have mixed feelings about giving the boss a gift.

“I’ve never done this or wanted to – then, my last boss was a really bad one, a bully," said Susan Moon of Seattle. "My current boss is terrific, I have more appreciation because of my immediate prior bad experience, and I’m finding myself wanting to find a small gift to 'gift up' this year.” 

Most employees who were comfortable with the idea of giving the boss a gift felt it should be more of a token gift rather than a big, under-the-tree type of present. “I usually just bring snacks for the staff and our boss on holiday weeks. They are all men, so they would eat anything I bring, but they always make me feel as though I saved the day when I bring food to work,” said Megan Okerstrom of San Angelo, Texas.

Where employees can really start to get resentful when it comes to gifting up is when bosses seem to expect (or at least accept) large, lavish gifts. “It still makes me mad that my co-workers at the dental office expected us to give $50 to get our bosses stuff like a new camera and a Longchamp bag," said Ky Ivany of Pomfret, Vt. "They were dentists; I think they can afford their own cameras.” 

Of course, the best gifts are priceless. “I like to give my boss the gift of pretending to care about my job every day,” said Jeff Mac of Albuquerque, N.M.

The type of organization you work for can have a lot to do with the practice of gifting up. Those in the military, who work for the government or who are members of unions are likely to find the practice frowned upon, if not banned outright.

Even if you leave the service, you might find some of those values sticking with you, come gift time. “My attitudes were formed in the Army, but I think they are universal,” said Rob Mood of Houston. “Demanding or even accepting 'stuff' from subordinates is a sure sign of abysmal leadership and probably much more rot at the heart.”

While some employers may enjoy or even expect gifts from their subordinates, others are uncomfortable with the idea. “From the perspective of a boss, don't buy me anything,” said Maggie Reed of Davenport, Iowa. “I am a firm believer in the separation of boss and employee for ethical reasons." 

Jody Gowdy of Maple Valley, Wash., echoed those sentiments. "I would never expect something and honestly find it uncomfortable when it has happened in years past. We give the employees something every year as a thank you for job well done. But I would say no."

If you do decide to give a present to the boss, experts have some advice on how to do it gracefully. “Make sure you keep it humble and a token of your appreciation," Masini advises. "It's inappropriate to 'one up' your boss's gift. It may make your boss feel uncomfortable.”  

Masini also notes that employees should make sure any gift is in line with their salary. "If you make minimum wage, and you give your boss an Hermes scarf or a ... bottle of champagne, they're going to think they're paying you too much or you're terrible with money.” 

Masini also warns employees to make sure to gift in the proper chain of command. "In other words, don't gift jump by ignoring your immediate boss, and gifting your boss's boss. Gift jumping is bad politics and will yield you in hot water.” 

How do you feel about the practice of gifting up? Tell us about it on Facebook.

Dana Macario is a Seattle-area writer who likes a small gift for a good boss – when you get a good one, it’s nice to let them know.

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