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If this is your first holiday season with your company you may want to check around and see if there are any policies in place about giving your boss a gift. Your Human Resource manual may have a policy that you need to know about. Many corporations forbid such exchange.
Employees may view one’s gift as brown-nosing while others who were not intending on buying a gift for the boss may now feel obligated to do so. It all depends on the company you work for and what is considered standard fair.

If where you work has more of a family type atmosphere then it is likely that the practice of buying for the boss is acceptable but do your research before you proceed. Appropriate gifts for bosses would include - Calendars, organizers, pen sets, food baskets, stationery, tea, coffee, or something along the line of relaxation squeeze balls.

Gag gifts – an absolute no-no!
Homemade items. This could be viewed as being too personal. However, it would be fine if you bake cookies for everyone or bring in some of your homemade jelly for everyone to enjoy during the season.
Gifts purchased at discount stores or dollar stores. You risk being viewed as being too cheap.
Food items such as turkeys. Do not assume all the people who work for you are meat eaters.

To avoid looking cheap and creating resentments among your employees, keep your gifts equitable and as general as possible.

Stay within the dollar limit stated. For most offices, this is usually set somewhere under $15.00.
What are the person’s hobbies? If they are avid golfers, consider a golf-related gift.
Do not be tempted by gag gifts. They are considered taboo for the workplace.
Wrap the gift. A nicely wrapped gift will add value to your gift plus demonstrate your ability to be organized and neat.
Do not be late with your gift. Have it ready for the day the gift-giving will take place.
What you choose to give and how you present your gift will say a lot about the type of person you are.

Find out the specifics - What has been done in the past? Is there a dollar limit set? When gifts are normally exchanged?
If there is a dollar limit, stick to it. Giving a bag of jellybeans to one coworker and an elaborate gift basket to another could cause resentments. If you feel the desire to go beyond the dollar limit, then this person would be considered more of a personal friend and therefore the gift should be exchanged outside of the working environment.