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Thinking of buying your supervisor a holiday gift? Think again. Think very carefully, advises blogger Penelope Trunk. Her advice: "Don't give your boss a gift." 

Well, there's one kind of gift she recommends: a handwritten note.

This missive should explain your appreciation for what your boss has done for you in the past year, and explain how lucky you feel to be working for him or her.

"Give very specific examples," Trunk says.

Easier said than done if you’re in a job you dislike and/or have a creep for a boss. If that's the case, maybe you can skip the whole thing based on the etiquette-based or actual corporate policies mentioned by Trunk's readers -- specifically, that giving should be "down" (supervisors to employees) rather than "up."

"Giving the boss a gift can be either bribery on your part or extortion on the boss's part," wrote one commenter. "In either case, it's a terrible idea."

But what if you're in a work environment where not giving a high-profile gift is professional suicide?

If that's the case, better follow the lead of older, wiser colleagues. I feel sorry for you, since the pressure to come up with the right kind of gift must be tough.

Even more ticklish: How much should you spend? One-third of the women surveyed by Connect: Professional Women's Network on LinkedIn spent $50 or less on a supervisor's gift; 6% spent more than $50.

The other 61% of survey respondents advise against giving at all.

"As a manager, I would be very uncomfortable with people giving me gifts," says one commenter. "I am convinced that managers have a duty to serve their employees, and all giving at holidays must be from managers to their teams."

To give or not to give?

Start by checking your workplace policy. Larger companies tend to have very specific rules, according to Randall S. Hansen of the Quintessential Careers website.

Hansen lists 16 specific tips in his post on holiday gift-giving. Among the most useful:

  • "Don't ever get something for the boss just to show up your co-workers."
  • "Stay within your (and the office) budget for the gifts, and don't go overboard . . . especially for the boss."
  • "Don't feel pressure to run out and buy a gift for the boss if he or she gives you one. But do send a thank-you note acknowledging the gift and expressing your gratitude."

Suppose there's no gift-giving precedent? It's probably smart to err on the side of caution and not give "up." Otherwise you run the risk of looking either naive or sycophantic.

However, I personally think a small gift is OK if your relationship is a positive one. The trick is not to go overboard. During my newspapering days, I gave gifts to my editor: art note card sets, books I thought she might like, a selection of homemade Christmas cookies (which she usually set out for all to enjoy).

She would give her writers things like bookstore gift cards with brief notes about her appreciation for our work during the year. I valued those notes, and now I wish I'd thought to write one to her.

Your own boss might be hankering for a little validation. Why not keep it real (and affordable) by writing a letter or giving a plate of holiday treats? If you're not a skilled baker, give a bowl of fruit or a box of candy.

Do this frugally by using a price comparison website, or watching the daily deal sites (check the secondary market for social buying vouchers, too, since you might find a discounted deal for cupcakes or other goodies).

Do you give your boss a gift? Why or why not?

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