The Holiday Hustle: What Executive Assistants Need to Know This Season

The holiday season hits differently when you’re an executive assistant. While most people are busy hanging decorations or planning their vacations, you’re knee-deep in managing schedules, organizing events, and fielding an onslaught of tasks that seem to multiply as the year winds down. But the holidays aren’t just about wrapping up the year; they’re also about navigating unique challenges that only crop up in December.

To help you breeze through the season with grace and confidence, here are some fresh perspectives on holiday-specific tasks and how to tackle them with finesse.

1. Balancing Professionalism and Festivity

The holidays come with an inherent clash: maintaining professionalism while embracing a festive atmosphere. Your executive might want to look approachable during this time but still maintain authority. Finding the right balance can often fall on you.

Tips to Manage:

• Tone Matters: Keep emails and meeting invites festive but professional. Swap out sterile subject lines like “December Update” for something warmer, such as “Wrapping Up the Year Together.”
• Decor Etiquette: If your office is decorating for the holidays, make sure the vibe is inclusive. Avoid overly specific themes and go for a seasonal aesthetic that feels welcoming to everyone.
• Celebrate Thoughtfully: Suggest small gestures, like hosting a team hot chocolate bar or sending personal thank-you emails from your executive. These details show personality without going overboard.

2. Prepping for the Season’s Social Pressures

Holiday events often require you to juggle more than logistics. As the gatekeeper, you might need to coach your executive on subtle social nuances, like remembering names, avoiding potential faux pas, or knowing when it’s time to leave a party gracefully.

Tips to Manage:

• Be Their Wingperson: Brief your executive on key attendees, including clients, board members, or influential team members they should connect with at holiday events.
• The Social Timer: Discreetly signal when it’s time to wrap up conversations or exit gracefully. A quick text or agreed-upon gesture works wonders.

3. Navigating Quiet Quarters and Last-Minute Chaos

December can swing from eerily quiet to overwhelmingly hectic. One day, half the office is out on PTO, leaving emails unanswered, and the next, an unexpected opportunity or crisis demands your full attention.

Tips to Manage:

• Anticipate Downtime: Use quieter days to organize files, clean up calendars, and prepare for Q1. Think of it as a holiday gift to your future self.
• Plan for Chaos: Keep an emergency contact list handy in case you need quick approvals or decisions while key players are out. Proactively ask for pre-approvals on items you know might pop up.
• Manage Expectations: Set boundaries for what is realistically achievable in the final weeks of the year. It’s okay to let some non-critical tasks roll into January.

4. Keeping Your Executive Media-Ready

For executives with a public-facing role, the holidays often mean more exposure, whether it’s a year-end media interview, a company town hall, or even a cheerful social media post. You’re part of the team that ensures they shine.

Tips to Manage:

• Media Prep: Help them rehearse for interviews or live events. Compile talking points, key statistics, and positive takeaways from the year.
• Curated Social Moments: If they’re posting on social media, encourage authenticity. A heartfelt message about the company’s successes or gratitude for the team can go a long way.
• Wardrobe SOS: Confirm outfits for public appearances ahead of time. Keep a backup suit, tie, or dress ready for emergencies.

5. The Tricky Task of Navigating Holiday Sentiments

The holidays aren’t all cheer for everyone. Some employees or clients might find this time emotionally challenging, and your executive may need guidance on how to navigate sensitive situations with compassion.

Tips to Manage:

• Stay Inclusive: Remind your executive to keep celebrations neutral and inclusive. A “winter celebration” or “year-end event” feels more welcoming than explicitly tying everything to Christmas.
• Provide Support: Be prepared to step in if tensions arise. Sometimes a thoughtful buffer, like arranging a quiet one-on-one conversation with a colleague, can help smooth things over.

6. Coordinating with Other EAs (and Making Them Your Allies)

The holiday season isn’t just about managing your executive’s calendar, it’s about collaborating with other assistants who are just as swamped as you are. Coordination is key, whether it’s scheduling joint meetings or arranging holiday greetings.

Tips to Manage:

• Create a Network: Reach out to fellow EAs early in the season to plan for overlapping responsibilities. A quick email thread or group chat can streamline communication.
• Be the Organizer: If there’s a big, cross-team holiday event or project, step up to organize it. This positions you as a leader and makes things run more smoothly.
• Share Resources: If you’ve found a great gift service or vendor, let your peers know. Building goodwill makes future collaborations even easier.

7. Managing the Year-End Budget Crunch

Holiday expenses can add up quickly, and as the assistant keeping an eye on spending, you’ll need to juggle generosity with fiscal responsibility.

Tips to Manage:

• Track Spending: Keep detailed records of holiday-related expenses, from catering to venues. Make sure you’re aligned with budget expectations to avoid surprises later.
• Negotiate Deals: Vendors often offer discounts during the holiday season. Ask about bulk discounts for gifts or negotiate reduced rates for services.

8. Avoid the “Oops, We Gifted That Last Year” Scenario

One of the quickest ways to lose the personal touch in gifting is accidentally giving the same gift twice to a key client or colleague. Keeping track of gifts distributed in your executive’s name over the years isn’t just thoughtful, it’s essential to maintaining their reputation for care and attention to detail.

Tips to Manage:

• Maintain a Gift Log: Create a running list of all gifts given out by your executive, organized by year. Include details like the type of gift, the occasion, and any notes (e.g., “loved it” or “needs something different next year”).
• Cross-Reference the List: Before finalizing this year’s gifts, double-check the log to avoid repeats. It’s worth the extra five minutes to ensure each recipient gets something fresh and memorable.
• Update in Real-Time: Don’t wait until the holiday rush to update your records. As soon as a gift goes out, add it to the log to keep everything current and accurate.

9. Don’t Forget to Enjoy the Season Yourself

It’s easy to get caught up in making everyone else’s holidays run smoothly and forget your own. But a stressed-out assistant isn’t an effective one, so taking care of yourself is non-negotiable.

Tips to Manage:

• Take Breaks: Schedule time to recharge, even if it’s just a quiet coffee break away from your desk.
• Set Realistic Goals: You can’t do everything, and that’s okay. Focus on what’s most impactful.
• Celebrate Your Wins: At the end of the season, reflect on all you accomplished. Treat yourself to something

The Bottom Line

The holiday season is a unique blend of chaos and celebration, and as an executive assistant, you’re the one keeping the balance. Whether you’re managing last-minute meetings, coordinating gifts, or helping your executive navigate the social and professional demands of the season, your ability to anticipate and organize is what ensures everything runs smoothly. Remember, your role isn’t just about handling tasks, it’s about creating an environment where your executive and their team can truly thrive during one of the busiest times of the year. So, stay prepared, stay flexible, and don’t forget to take a moment to celebrate your own wins this holiday season.