According to reference-checking firm Allison & Taylor, it definitely is a good idea to send your boss (and his or her boss) an appropriate holiday greeting. It’s an important way to send the message that you value your relationship with the company, and respect these people as individuals. (Additionally, surveys have shown that they are widely appreciated in the business world as a whole; recipients are more likely to do business with a company or individual that sends holiday greeting cards.)
When it comes to e-cards, Allison & Taylor suggests you forgo them for a variety of reasons. Many senior managers are older and may reflect an “old school” mentality. A greeting card sent via electronic means may be regarded by them as inappropriate, perhaps even cavalier. Additionally, such e-cards also tend to lack the personal touch of a card mailed individually to the boss’s door; e-cards and social media holiday greetings often are sent en masse, or – in the case of social media greetings – can be done as spur-of-the-moment responses to a comment seen on Facebook or some similar venue.
While sending out holiday cards is almost certainly a good idea, even this generous gesture can backfire if the proper protocols aren't observed. Here are some reasons why a traditional greeting card is a good idea and tips for sending an appropriate card: