‘Tis The Season For Holiday Prep: How to Avoid Awkwardness

Ah, the holidays! For workplaces everywhere, it’s a time for joy, togetherness, letting loose, and, if we’re not careful, some opportunity for workplace awkwardness that gets to live on in our memories forever. As HR pros we’ve seen firsthand how a little proactive planning can turn the potential for holiday chaos into a season of smooth sailing. 

Here’s why now (not next week, not mid-December) is the time to have clear, kind conversations with your team about workplace closures, expectations for responsiveness, time off, and… holiday parties. Because if you don’t set expectations, employee assumptions will set them for you.

In my first job, I didn’t think to ask about holiday closures. No one told me when the office would be closed, so I assumed we’d be working straight through and didn’t want to seem presumptuous by asking. I told my family I’d be busy the week between Christmas and New Year’s and didn’t make plans to travel home.

So on December 18th when my boss casually mentioned, “I can’t wait for the week and a half off (in two days)… it’s going to be so nice to get some down time!” cue me frantically scrambling to salvage a holiday plan while everyone else already had cat sitters booked, get-togethers scheduled, and Netflix queues filled. Don’t get me wrong - it was such a nice surprise, but also there was a takeaway for me: employees need clarity, and they need it early.

Rule #1: Let your team know the when of holiday closures. 

Whether you’re closing the office, staying open with a skeleton crew, or asking employees to use vacation time, be explicit. Spell it out in an email, a meeting, a Slack message, whatever works best for your team.

Why it matters: People have lives! Families to visit, friends to see, or maybe just some couch time they’d like to pencil in. Giving advance notice shows respect for their time and lets them plan accordingly.

Pro Tip: If you don’t have a formal holiday closure policy, now’s a great time to start. Communicate the dates this year, and think about how to handle this consistently in future years.

Rule #2: Time Off: Don’t Wing It

It’s too late this year, but next year, ask staff to think about and request their time off well before the chaos of December sets in. (This saves you from spending your holidays untangling the “Who gets New Year’s Eve off?” debate).

Be transparent about how time-off requests will be prioritized. First-come-first-served? Seniority? Rock-paper-scissors? Remove potential for misunderstandings or hard feelings.

If you’re staying open, remind employees that holiday workloads may differ. Communicate expectations early so no one feels blindsided.

Rule #3: Holiday Parties: Think Fun, not Frat Party

The workplace holiday party can be a delicate dance of festivity and professionalism. In theory, it’s a chance to celebrate the year’s successes. In practice, it can sometimes feel like a reality TV show where HR is the villain (or leaves by 9 pm to avoid seeing things they can’t unsee).

Here’s how to keep holiday celebrations joyful and appropriate (and ideally avoid the “one-too-many-mulled-wine” phase entirely):

• Set the tone: Let employees know the party is a celebration, not a frat party. A light reminder about professionalism (delivered clearly, but with humour) can go a long way.

• Consider everyone: Keep the event inclusive. Non-alcoholic options, dietary accommodations, and avoiding activities that make people feel uncomfy (karaoke can go either way).

• Pro Tip: If alcohol is involved, provide transportation options so that everyone gets home safely. As the boss, it’s part of your job. 

The holidays should be a time for joy, connection, and a little down time, not confusion or stress. By talking about holiday closures, time off, and celebrations now, you’re giving your team the gift of clarity. Your type As will thank you!

What’s your plan for holiday prep? It’s never too early to sleigh it and make this year’s holiday party memorable for the right reasons! 

Also, if you need help with messaging, holiday policies (or a chaperone), reach out. We’ve got you covered!