Help! I Need to Get the Holidays Right This Year

Dear Mike,??

After years of familiar, yet somewhat disorganized holiday celebrations at our company, I've just been promoted to division head, which brings with it the ambiguous charm of being able to impose some structure on the holiday season. As I started thinking all of this over, however, I was struck by how much etiquette is actually involved in the holiday season. I feel woefully unprepared to take responsibility for getting everything right – at least, not without a little guidance from you.?????

First of all, I'm toying with the idea of a company-wide Secret Santa. But then I realized, that’s probably not even what we call it anymore, right? There must be a much more inclusive term for that kind of exchange. Is that true for everything about the holidays? How much is too much consideration? Won’t we lose some of the spirit of the holiday season if we obsess over making sure the language doesn’t offend? Or is it worth being painstaking about that stuff just to make sure we don’t end up paying for it on the back end? I’m not trying to be a pessimist, but I don’t want to put us at risk over something as simple as using the word “Santa” in the office if I should avoid it. If we do some kind of gift exchange, should our executives participate? How can we keep it fair and fun, without making it weird???

And don't get me started on the holiday party. I want it to be a way for us to ring in the next working year and start things off right, but it seems impossible to avoid offending someone or leaving something open to the wrong kind of interpretation. We’re all used to having booze there and everyone cutting loose, but if it’s all going to be my responsibility, I’m half-considering making everyone drink apple juice and just calling it a day.??

How much holiday cheer is too much? How can I be sure I’m not getting it totally wrong and what’s the right balance to strike? Help me not kill the joy of the season or put the company at risk with my efforts at revelry. Please.????

Warm holiday wishes,??

Santa’s Little Helper?

With all the talk of political correctness in the news, we can all relate to worrying that well-meaning holiday fun will turn into an office disaster. And, If you’re subbing alcohol for apple juice this year, you may have reason to worry. For most people, that’s the best part of the whole season! That is, if you like next-day hangovers and awkward conversations that involve statements like, “I don’t know why Mary is mad at you. It might have something to do with that fact that you told her she looked better with the Santa beard on.”??

What you’re doing is admirable. Don’t be so quick to worry or assume that people will misconstrue your intent. This time of year, regardless of where you sit on the religious spectrum, you’re likely celebrating something – even if it’s just a few days off from work. As long as you find a way to celebrate that festive spirit and your employees, you should be okay.??

The holiday season has a way of either boosting people up or stressing them out

The holiday season has a way of either boosting people up or stressing them out. It’s a hectic time of year and that shows up in the office. The great thing about celebrating is that it’s a chance to appeal to both types of people. Why not frame it as an “end-of-the-year” party and an opportunity to celebrate your hardworking colleagues? After all, the year is ending – no one can argue with that – and everyone likes and deserves some appreciation in the workplace. Now, they may be a little annoyed that the company isn’t offering booze, but that’s a gripe (and potential liability) for HR to field.?

While Secret Santa is still a thing in some offices, a gift exchange is also a nice conclusion to year-end parties. Depending on your company culture, you might even do it White Elephant style, with gag gifts. In my experience, the reasons for not doing Secret Santa are less political than they are related to interpersonal dynamics. An open gift exchange, where everyone brings a gift within an agreed upon price range (like $25), can be a lot more fun. And, often, they’re lower stress.??

Bring the employees in on it, bring the executives, bring the whole team. Something I’ve learned in life (and work) is that everyone is looking for a sense of community and camaraderie. A gift exchange is a great chance for higher-ups to humanize themselves. If you're still concerned, it can even be done anonymously to further reduce the chances of any awkwardness.??

Something I’ve learned in life (and work) is that everyone is looking for a sense of community and camaraderie

Like any good Christmas story, this one offers up a moral: There are different ways to creatively celebrate the close of year, the start of the next, all while giving people a little time to breathe. And yes, it’s probably okay to wear a Santa costume, an eagle costume, or whatever costume best embodies your festive spirit.?

In today's business climate, most of us feel unsure at least a few times a week. If you have a question about a difficult workplace scenario, my inbox is always open. Message me here on LinkedIn or leave your questions for me anonymously. After 22 years as a serial fintech entrepreneur, I've averted my share of disasters. Let me help you outsmart yours.