Who it's for: Ma, Pa and the in-laws, your closest confidantes, valuable clients, your boss.
The message: I really value our relationship.
How to do it right: Send a classic, crisp card with a short but genuine pen scrawl. In your best cursive, ask after their family (or dog or golf game). “[A card] has a lot more impact,” says Jay Remer, an etiquette consultant in St. Andrews, N.B. “[You've] taken the time, a special moment for that one person.” Hand-pick personalized ones for the really special people. The downsides to card-writing: You're killing a few trees, it costs some dough, and you may suffer a little arm cramping. But it's worth the time and effort, Mr. Remer says.
How to do it wrong: Sending out a mass year-in-review holiday letter. Impersonal and often self-gratifying, “it [can seem] like ‘Let's just wholesale this thing,'” Mr. Remer says.
Who it's for: Your expat friend in Europe, the couple you'd like to get to know better.
The message: Let's catch up.
How to do it right: Have a good old-fashioned, distraction-free gab fest, says Louise Fox of the Etiquette Ladies consulting firm in Toronto. Set aside some time and don't call on your cell while you're doing last-minute Christmas shopping. Make genuine plans to see each other in the new year. A phone call also shows you haven't disappeared into a digital black hole and you still like hearing the sound of a pal's voice, Mr. Remer adds. “It's not good for society to lose that element of civility.”
How to do it wrong: Proclaim “happy holidays” then ask them for a favour. Not cool and not genuine. “[Don't call and] say, ‘Oh by the way …'” Ms. Fox says.
Who it's for: Favourite IM peeps, clients you're trying to impress, cubicle-mates.
The message it sends: I'm green, tech savvy and down with the times.
How to do it right: Look for something classy and simple or intentionally goofy. If you can design it yourself, even better. Personalize the e-card with photos or video and a brief, thoughtful message. Tamar Weinberg, a social media consultant in New York has made video cards using the “Elf Yourself” tool on jibjab.com, which lets you smack a photo of your head on virtual Santas and Santa's helpers. People loved it, she says.
How to do it wrong: By spamming people. And don't forget to test drive the e-card, says Glenda Rissman, a partner with q30, a design firm in Toronto. “You don't want to send someone a link to this and then they can't open it.”
Personalized e-mail or text, Facebook message or direct message on Twitter
Who it's for: Your social networking crew, people you've never met in person or talked to on the phone
The message: You're in my top 10. Or 20. Or something like that.
How to do it right: Slip in a memory from the year, an inside joke or two, or a reference only they would appreciate. More casual than a card or a letter, the holiday message that comes the same way you always communicate needs that extra detail to be special. Consider the person's medium of choice and tune in to generational differences, Ms. Fox says. If your 14-year-old cousin is a text-a-holic, send her happy hols that way.
How to do it wrong: Writing the person's name at the top, but slapping the same cookie-cutter message in the type. While “everybody likes to be thought of,” Ms. Fox notes, a generic message is a generic message. Don't pretend it's not.
Mass text, mass e-mail, Facebook status update or Twitter blast
Who it's for: Your tweeps, marginal Facebook friends, everybody else in your address book.
The message it sends: I've got the holiday warm and fuzzies.
How to do it right: Approach it as a general spreading of mirth, Mr. Remer says. “You're really sharing a thought you have of yourself.” But you can still make a mass blast feel more personal by addressing the whack of them as your valued peeps. A message such as “Happy Holidays, my beautiful friends” or “I'm thinking of you this Christmas” should suffice. Just make sure the sentiment is genuine, or try to at least make it memorable, Ms. Weinberg suggests.
How to do it wrong: Hey guyz, happy hollydayz. So glad it's Xmas, woot!