"Are you planning to send holiday cards this year?" 

That's a question that several fellow entrepreneurs in my network have asked these past few weeks. My answer -- Yes, of course -- seemed to catch them by surprise, not because it's unusual to send holiday cards but because I was doing it on behalf of my business. Their immediate next question, about how I decide which cards to send and what to say inside of them, indicated my colleagues' anxiety over commercializing a personal tradition and coming across as "too market-y."

My own approach is to use holiday cards to express gratitude, particularly to advisers and key decision-makers who have helped the business grow in the past year. Saying "thank you," and generating the list of people I'm grateful for, is one of the most emotive and cathartic experiences of the year.

I sensed that my colleagues could use a little more advice, so I reached out to Toby  Hextall at MOO, which creates custom-designed business stationery and promotional materials. As MOO's Director of Product Design, he knows a thing or two about effective ways to communicate graphically, tastefully, and effectively.

I asked him how entrepreneurs can best navigate the waters of communicating around the holidays, and he shared his advice on why it makes sense for entrepreneurs to reach out during the holiday season; how to do it tastefully and authentically; and the biggest mistake to avoid.

An Excuse to Connect

Moo sees an annual spike in greeting cards orders leading up to the holiday season from both startups and large businesses alike. Which makes sense, since it's the perfect opportunity to reconnect with customers. Hextall sees the holiday card orders fall into one of three general categories:

  1. Keeping in touch. "You've got the perfect reason to reach out to a long-lost business contact," he said.
  2. Soft sell. "It's a chance to remind people of your skills and your landmark moments of the past year without giving them the hard sell," Hextall commented.
  3. Saying thank you. "There's nothing more likely to make people smile than an unprompted thank you during the holidays, which just might put them on your radar for the year ahead," he said.

Make Them Personal

Just because there are strong reasons for entrepreneurs to reach out to their network and clients during the holiday season doesn't mean that it's simple. Hextall's advice? Be careful to distinguish yourself in a way that aligns authentically with your brand.

"With any promotional products, you want to make sure your business' story and personality shines through," he said. "And this is also true of holiday cards."

Some specific tips:

  • "Our biggest piece of advice is to make it personal," Hextall said. "Whether you're reaching out to business advisors or top customers, adding a handwritten note to your holiday cards can make all the difference."
  • Including a small gift can also go a long way in making it special and recognizing how the recipient has helped and supported your business. 
  • Showcasing your work prominently can be a great way to be sure your business' personality shines through.
  • Humor can also be helpful if appropriate for your business and customers. "Making your holiday cards useful or hilariously funny (if appropriate for your business and customers) will increase the chance your customers will keep them and be reminded of your businesses," Hextall said. "Just make them really very funny."
  • Picking a different size or shape card can help it stand out from the pile and make it memorable.

Avoid the Team Picture--Switch it Up

In closing, I asked Hextall whether there was a common mistake he sees Moo's customers making, that he would advise entrepreneurs to avoid when it comes to holiday communications for new businesses.

"We see lots of businesses using a team picture on their holiday cards," he replied. "This can be great for some businesses where the one-on-one connection to customers is paramount, but it doesn't mean there's much motivation to keep it."