Holiday Greetings Etiquette, Decoded

Deciding how your business should approach holiday greetings is enough to make anyone sweat. Paperless Post’s cofounder walks us through it.

Holiday Greetings Etiquette, Decoded
[Photo: Lilyana Vynogradova via Shutterstock]

James Hirschfeld, cofounder of Paperless Post, can pinpoint the exact moment we collectively started thinking about the holidays this year: It all started November 2nd, when daylight saving ended. “It’s like some sort of deep-seated animalistic instinct,” he says. “We see an incredible spike in traffic when daylight saving happens; it’s like it clicks in everyone’s minds subconsciously from one day to the next that the holidays are upon us.” And it’s true, it’s suddenly time to take care of important holiday business: making a Christmas list, finding the least awkward family photo for the annual newsletter, and buying stacks of greeting cards to send colleagues, business partners, and clients.


Sending holiday greetings in the workplace can be a tricky business, particularly as social norms are quickly changing. Have we reached the moment when we can send clients online greeting cards? Will an e-card look lame sandwiched between marketing emails for holiday sales? These are all good questions, but Hirschfeld says that we should start with underlying principles. “This is going to sound strange coming from a guy who’s in the business of selling greeting cards,” he says. “But the most important question to ask yourself is why you are sending a card in the first place. There is absolutely nothing worse than receiving a perfunctory greeting from a business.”

It has now become customary for businesspeople to send customers and corporate partners holiday greetings. In December, our mailboxes–both physical and digital–become clogged with cheerful, wintery messages from every company with which we transact. Hirschfeld says that if you want to stand out in the midst of all of this glitter and noise, your holiday greeting must be personal, original, and thoughtful–otherwise, it might be best not to even bother. “The last thing you want as a business is for your holiday card to be seen as spam or clutter,” says Hirschfeld.

The most important piece of advice Hirschfeld has to offer is to make sure that your holiday greeting comes from one particular person, rather than from the company as a whole. Nobody wants to see a generic card from an LLC, no matter how sparkly it is. If you are in charge of buying a card for your organization, be sure it is designed with a space for a company representative to include a personalized message. “It’s more of an operational burden, but it’s nice to establish that connection between the sender and the receiver,” says Hirschfeld. With the right execution, a holiday card can be a beautiful way to deepen relationships with customers and partners. If done poorly, it can feel like a tacky marketing ploy. “Now is not the time to direct the recipient to your awesome new website redesign or post-Christmas sale,” he says.

One of Paperless Post’s holiday cards

Hirschfeld tells me that Paperless Post itself sends out about 200 holiday greetings a year. “You’d think we would go crazy with our own holiday cards because we make them for a living,” he says. “But we are not interested in using the holidays as a lead generation opportunity.” Instead, Hirschfeld sends little holiday thank-you notes to business partners that he is grateful for: Cards go out to the company lawyer and accountant he speaks with every week, his investor’s assistant who gets him on the calendar even during busy times, the colleague’s wife who brings cupcakes into the office sometimes. “I see sending cards as a way for us to act like a family,” he says.

Oh, and he sends e-cards, rather than paper cards, although Paperless Post offers both options. Hirschfeld has seen more and more companies move to digital holiday invitations and greeting cards over the last couple of years, revealing a shift in the way that e-cards are perceived. At one time, online cards may have been seen as a cheaper and less thoughtful option, but today, as more and more business is conducted online, digital messages are on trend.

If you are deciding whether to go the paper or online route, Hirschfeld says you need to think carefully about what your brand stands for. “It really comes down to the values you represent as a company,” he says. For instance, a luxury goods company might want to convey their brand aesthetic by sending beautiful cards printed on thick cardstock. A nonprofit, on the other hand, may not want to invest a lot of money in purchasing physical cards because those funds come from the donors’ pockets; a more thoughtful approach would be to send a well designed e-card with a personalized message to each recipient. That said, an e-card will be competing with other holiday marketing messages in the recipient’s inbox, so there is more pressure to make the card’s message stand out. “When you move from the real world to online, you cannot communicate how much you appreciate the recipient through the sheer cost of the card, so the authenticity of the message matters more,” he says.


When it comes to the content of the card, there is really no single right way to be thoughtful in your message: Anything that shows warmth and appreciation to the recipient works well. However, there are certain things to stay away from. Drunk polar bears, for instance. “There’s a lot of drinking in holiday cards,” Hirschfeld says. “There are images of eggnog, hot toddy, champagne, and then there are all the a pictures of animals drinking.” While these kinds of cards are fun for friends, it might be best to stay clear of them in corporate cards, even if your branding is urban and fun, because you don’t want to potentially offend non-drinkers or people who celebrate Christmas as a religious holiday.

A Paperless Post card

Speaking of which, it’s also a good idea to stay clear of denominational greetings, since there are many Americans who do not celebrate specific holidays in December. Hirschfeld has noticed that rather than building community by rallying under a specific religious holiday, people like to support good causes around the holidays, such as animal rights or hunger prevention. To cater to this need, Paperless Post has started offering digital “stamps” that people can buy for their e-cards that show support for a particular charity. “Causes have become a way for people from very different backgrounds to feel a bond with one another that has nothing to do with a religious tradition,” he says.

Within these constraints, Hirschfeld finds himself constantly surprised by how creative, intimate, and personal businesses are with their holiday greetings: Cards run the gamut from pictures of silvery pine trees brushing against city landmarks to photos of employees wearing their ugliest sweaters. Done right, holiday greeting cards can be a way to build stronger business relationships and make the workplace feel a little warmer.

Just steer clear of that drunk polar bear.

About the author

Elizabeth Segran, Ph.D., is a staff writer at Fast Company. She lives in Cambridge, Massachusetts.