by CIO Staff

Holiday Business: Do’s and Don’ts for sending and receiving gifts and attending holiday parties

Dec 08, 20068 mins
Relationship Building

Between all the holiday parties and good tidings sent in the form of greeting cards, special luncheons and Harry & David fruit baskets, the Yuletide season presents ample opportunities for business people to reconnect with one another, deepen their relationships and express their gratitude for colleagues’ and customers’ business and support.

And ample opportunities for good intentions to backfire. All it takes is one too many servings of hot buttered rum before someone is swinging from the chandeliers at the holiday party. Or wishing devoutly Jewish/Muslim/atheist business partners a Merry Christmas. Or giving an extravagant gift to a customer that smacks of a bribe. (To read about the luxuries vendors have offered to some CIOs, check out Doesn’t Matter If You’ve Been Bad or Good from the CIO magazine archives.)

Given all the potential missteps, it’s no surprise that many companies say “bah, humbug” when it comes to the holidays, especially to exchanging gifts internally and externally.

Wendy Cebula, the CIO of the Lexington, Mass.-based graphic design and printing company VistaPrint, says her company discourages gift-giving because thinking about what kinds of gifts to buy, for whom, and how much money to spend tends to generate more stress than goodwill among employees.

The business process outsourcing services provider US Technology Resources also frowns on exchanging presents. “We try to avoid giving holiday gifts internally and externally,” says Bob Dutile, US Technology Resources’ general manager of enterprise consulting. “The vast majority of our customers have fairly significant limits on accepting gifts, and we have our own limit on acceptance of gifts from our own external business partners.”

Companies seem to make up for any Grinch-like behavior by inundating the U.S. Postal Service with holiday cards. Dutile plans to send cards to 60 people this year, including 10 of his co-workers. He also plans to send a “Happy Holidays” e-mail to approximately 200 people in his organization. He sees sending out holiday greetings as an opportunity to keep in touch with associates. “We’re all so busy all the time. Sending cards around the holidays helps make sure you’re renewing that acquaintance even if you haven’t been in touch all year,” he says.

To make the holiday season as stress-free and productive as possible—and to prevent any awkward faux pas—we offer the following Do’s and Don’ts related to sending and receiving cards and gifts, and attending holiday parties.

On giving and receiving holiday gifts and sending cards…

  • Heed corporate policies regarding the acceptance of gifts. Many companies prohibit their employees from accepting gifts valued over a certain amount of money. So before you bestow that $115 bottle of Sean Thackrey’s “Orion” Syrah on a client or business partner, find out if your recipient is allowed to accept gifts and if any price cap exists. Etiquette expert Peggy Post, the great granddaughter-in-law of Emily Post, recommends calling your recipient’s human resources department to find out if such a policy exists. Don’t forget to tell the HR rep who you are and why you’re inquiring. Giving an extravagant gift can look like a bribe, and your clients will respect you more if you don’t put them in a compromising position.
  • Return gifts that violate your company’s policy on the acceptance of gifts. If you’re on the receiving end of a vendor’s largesse, there is a dignified way to return extravagant gifts. Post suggests writing a note to the giver that expresses your gratitude for the gesture and that explains that you can’t accept the bottle of wine or the Super Bowl tickets because of a company policy and state what the policy is. She also advises recipients to keep a copy of their note in case the gift-giving incident becomes an issue.
  • Give your direct reports a gift. Post says small tokens such as gift certificates, plants and food items are a good way to express your gratitude for their hard work during the year.
  • Be discreet. “If you’re going to give a gift to a coworker, do it discreetly,” says Post. She recommends making a lunch date with your coworker and presenting the gift to her then. Exchanging presents outside the office prevents awkward situations, such as other coworkers wondering why you didn’t give gifts to them, or making colleagues who chose not to exchange presents remorseful for their decision.
  • Consider your recipients’ interests when selecting a gift. If you know, for example, that your assistant is an avid reader, give her a gift certificate to a book store. Putting some thought into your selection will make the gift more meaningful to the receiver. After all, there’s nothing that says, “I don’t care” more than a generic coffee mug.
  • Be a sport. If someone organizes a secret Santa or Yankee swap, Post says buck up and participate.
  • Say thank you. If you thank the giver in person, “be sincere,” says Post, adding that a hand-written thank you note is an extra touch. She says it’s especially important for employees to thank their bosses for gifts because the thank-you note presents an opportunity for employees to acknowledge the support and coaching their bosses have given to them throughout the year.


  • Give your boss a gift. “It can look like you’re trying to curry favor,” says Post.
  • Break the bank. Spend what you can afford, but even if you can afford to spend hundreds of dollars, doing so is inappropriate, says Post. After all, these are your coworkers, not the Royal Family.
  • Purchase anything for coworkers at Spencer Gifts. Sure, gag gifts are fun and often elicit chuckles, but they’re just not appropriate for the office. This isn’t a bachelor or bachelorette party, so select tasteful items.
  • Send a cheerful holiday card to someone who’s recently lost a loved one. In this context, light-hearted notes can come off as insensitive. Instead, says Post, send someone who’s grieving a “thinking of you” card.
  • Send a card with a religious message to someone who doesn’t share that faith. Just because Wal-Mart is wishing everyone walking through its doors a hearty “Merry Christmas” doesn’t mean you should. If you know that everyone on your list celebrates Christmas, then go ahead and send them a card with the baby Jesus on it if you are so moved. But if you don’t know who on your list celebrates what, simply send out a “seasons greetings” card. You’ll still show your contacts that you’re thinking of them and you won’t risk offending anyone.
  • Send cards to everyone in your contact list. VistaPrint’s Cebula says she sends out 20 to 30 holiday cards to business associates each year. “I want to make sure my recipients immediately recognize who the card is from,” she says. Plus, sending fewer cards makes personalizing them easier.
  • Feel obligated to sign every card by hand. Believe it or not, you don’t have to pen any notes in these cards, or even sign your name by hand. Post says pre-printed cards are perfectly acceptable in the business world since they’re “quasi-commercial” anyway. “It’s much warmer to write the hand-written whatever, but since some companies send out hundreds of cards, it’s not possible to sign them all,” she says.

On conducting yourself at the corporate holiday party…


  • Dress to impress. The whole company is going to be at the party, including the top execs, so show off your impeccable style. Unearth the fancy cuff links hidden away in the darkest corner of your bureau. Shine your shoes. Dust off your Swarovski crystal evening bag and get ready to make an entrance!
  • Work the room. It’s fine to hang out with your regular crowd, but don’t miss out on the opportunity to meet new people and deepen your relationships with acquaintances. You never know when you’re going to need one of these people to help you sell an idea inside the company. VistaPrint’s Wendy Cebula says holiday parties are great for interacting with coworkers you don’t see every day. Her company invites its board members and investors to its holiday party, which makes the event a good opportunity for people to network with them, she adds. (For more ideas on taking advantage of holiday networking opportunities, see Debra Feldman’s Career Boost column.)


  • Get drunk. Let’s face it, corporate holiday parties can be awkward social situations, and sometimes you’d like a little liquid courage to loosen up. But don’t loosen up too much. According to a survey of members of WorldWIT, an online community for professional women, 75 percent of respondents said drinking too much at corporate holiday parties was their biggest regret. Even if you don’t remember making a spectacle of yourself after throwing back too many cocktails the previous night, your co-workers will, and rest assured the incident will haunt you like the Ghost of Christmas Past.

Meridith Levinson is senior online editor at