Thinking about sending the boss (or a “Boss of Christmas Past”) a holiday card? If “yes”, should you be thinking of a state-of-the-art e-card/social media greeting, or a “snail-mailed” traditional card?

First, note that you probably have a good idea in sending your boss an appropriate holiday greeting. The greeting card industry estimates overall sales of 7 billion in greeting cards for 2011. And, a recent survey quoted 50% of holiday card recipients as indicating they were more likely to do future business with a company (or an individual) that sends holiday greeting cards. With your co-workers vying with you for the boss’s favor, your holiday card might prove to be a small, but decisive, differentiator.

Here are some reasons why your greeting card is a good idea:

1.    Connecting with your boss (or former boss) will help keep you top-of-mind in their awareness, translating to possible future support or opportunity.

2.    Sending your boss (also former bosses, colleagues, suppliers, etc.) a card demonstrates a personal touch to accompany your business relationship.

3.    Staying in touch with bosses and colleagues via a holiday card is a subtle yet highly effective form of networking. (It’s also less expensive than taking them to lunch, and won’t violate corporate edicts if sent via personal mail.)

4.    Staying in the favor of your prospective employment references (particularly former bosses) is critical to your future employment success. The reference-checking firm Allison & Taylor notes that approximately half of all reference checks they conduct reveal negative input from the references. Consider that a greeting card could prove to be a small, but critical, investment in your professional future.

5.    Developing and maintaining positive relationships with your boss, co-workers, and former bosses will ultimately be a cornerstone of success in your career.

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 additional guidelines to ensure your card is well received:

1.    Choose a high-quality holiday card that allows no possibility of offending its recipient. Remember that not everyone celebrates Christmas – be mindful of religious and cultural nuances, particularly with your international recipients.

2.    Choose a design that is appropriate for your business associates.

3.    Include one of your business cards inside the greeting card. This small insertion ensures that your recipients have your most current contact information and will reinforce your name with the card’s recipient.

4.    Be sure that the inscriptions on the outside of the card are both legible and attractive. Consider using a form of calligraphy to make your recipient’s name and address visibly pleasing. Also, be sure to include your return address on the mailing envelope.

5.    Sign each card personally. It only takes a moment to sign your name and write a short greeting, and your business associates will notice and appreciate this more personal gesture.

6.    Check the spelling of your contacts and their corporate name. Any good points you’ll score with a holiday card will be lost if you misspell your contact’s name or corporate information.

7.    Keep your contact list accurate and up-to-date. Make sure you’re not sending a card to someone who has left the department or the company.

8.    Don’t be late. In life and in business, timing is everything. Remember that many companies close during the holidays and people take a vacation to be with family, so send your cards early. Also, note the possibility that a recipient of your card may want (out of consideration or guilt) to respond with a card back to you prior to the holidays. Aim to have all your corporate holiday cards in the mail no later than December 15 if you’re sending them within the U.S., or earlier if you’re sending them via international mail.

Note that these guidelines address a traditional card sent via the Postal Service.  In our high-tech age, is an e-card or social media greeting just as good?

The answer is “probably not”, 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.  Such greetings also tend to lack the “personal touch” of a card mailed individually to the boss’s door – e-cards and social media holiday greetings are often 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 it’s possible that executives in high-tech industries might appreciate the use of cyberspace for holiday greetings, it’s usually best to mind the adage “When in doubt, better to avoid.”  In this case, you aren’t likely to go wrong with thoughtful, traditional holiday greeting cards that can go a long way in making a good impression on all your business contacts. Cultivating good relationships this holiday season will help ensure your professional success tomorrow.

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