EA Secrets: Holiday Edition, Surviving the Season’s Wildest Office Moments

The holidays in an office should be merry and bright, but if you’re an executive assistant, they can feel more like a marathon you didn’t sign up for. From awkward Secret Santas to chaotic meetings, the season offers plenty of challenges and, let’s be real, a ton of potential disasters. These are the moments that test your patience and creativity, and make for the best stories later.

Here are some real, or painfully believable, tales from the trenches of holiday EA life, paired with lessons that might just save your sanity this season.

1. The Holiday Card That Went Way Too Far

Office holiday cards are supposed to be simple, a cheerful photo or a well-designed e-card sent out to clients and colleagues. But one EA shared how a seemingly innocent card turned into a full-blown drama: “Our executive wanted to make a holiday card that would ‘stand out.’ They insisted on a photoshoot in front of the company’s logo, complete with Santa hats. It didn’t sound too bad, until they decided to add our entire team to the card.”

The problem? “No one could agree on what to wear, half the staff was out sick or on PTO, and the final product ended up looking like a rushed family reunion. To top it off, the printer messed up the order, and we had 200 cards with the wrong names on them. I spent three days trying to fix it, only for most people to say, ‘Oh, I don’t even keep holiday cards.’”

Lesson Learned: Stick to simple, professional designs for holiday cards, and if possible, go digital. The time you save will be worth it.

2. The Holiday Potluck That Turned into a Food Fiasco

Potlucks are supposed to bring people together, but for one EA, it became a memory they’d never forget. “Someone brought shrimp cocktail to our office holiday potluck, which seemed fine, until they forgot to refrigerate it. By the time lunch rolled around, it had been sitting out for hours.”

What happened next? “Half the team got food poisoning, and I spent the afternoon fielding calls from employees calling in sick. My boss jokingly asked if we should hire a ‘potluck safety officer’ for the next year.”

Lesson Learned: If your office insists on a potluck, send out reminders about food safety. Better yet, suggest a catered event to avoid the risk altogether.

3. The Meeting That Refused to End

Holiday meetings are hard enough to sit through, but one assistant described a nightmare scenario that lasted for hours. “Our executive scheduled a ‘quick’ Q1 planning meeting two days before Christmas. Everyone thought it would take 30 minutes, but it turned into a three-hour deep dive with no breaks. People were visibly checking their watches.”

The kicker? “Halfway through, someone brought in a tray of cookies, which only made everyone hungrier and crankier. The meeting finally ended when my boss realized they were late for another appointment.”

Lesson Learned: Keep holiday meetings as short and focused as possible. Draft an agenda and set clear time limits so everyone can enjoy the season instead of resenting it.

4. The Holiday Travel Meltdown

For assistants managing holiday travel, disaster can strike when you least expect it. One EA shared their nightmare: “My executive was traveling to a client meeting on December 23rd, and their flight got canceled due to bad weather. They called me in a panic because they were stuck in an airport with no Wi-Fi and couldn’t reschedule online.”

“I spent two hours on hold with the airline trying to rebook their flight. Meanwhile, they were calling me every 10 minutes to vent. It was chaotic, but we eventually found them a seat on a red-eye flight. They made the meeting, but I was ready to throw my phone out the window.”

Lesson Learned: Always have contingency plans for holiday travel. Book flexible tickets, confirm lounge access, and have alternative travel options ready for emergencies.

5. When Family Brings the Chaos to the Office

The holidays are about spending time with loved ones, but sometimes that happens in the wrong place. “One December, my boss’s spouse and kids decided to surprise them by showing up at the office with holiday sweaters and cookies. While it was sweet in theory, my boss was in back-to-back meetings.”

It quickly turned chaotic. “The kids were running around the conference room, and the spouse started asking me if I could ‘squeeze in’ a quick meeting to discuss their holiday travel plans. I ended up herding everyone into the breakroom with hot chocolate and convincing them to wait until later.”

Lesson Learned: If family members show up unannounced, handle the situation with patience but firm boundaries. Redirect them to a time that works better for your executive.

6. Caroling Chaos in the Conference Room

Office caroling seems like a great way to spread holiday cheer, until it goes wrong. “Our HR department organized caroling as a surprise for the office. They had good intentions, but not everyone was thrilled to be serenaded during work hours.”

The real horror struck when one employee decided to join in despite clearly having a cold. “They started coughing mid-song, and the awkwardness was palpable. My boss looked at me and mouthed, ‘Make it stop.’”

Lesson Learned: Office festivities are great, but keep them optional and brief. Not everyone wants their workday interrupted by off-key renditions of ‘Jingle Bells.’

The Bottom Line

The holidays can bring plenty of joy, but for executive assistants, they can also bring unique challenges that require quick thinking, creativity, and the patience of a saint. Whether it’s managing a potluck disaster, navigating family surprises, or salvaging travel plans, every obstacle is a chance to showcase your ability to handle anything the season throws at you. And hey, at least you’ll have some great stories to share when January rolls around.