Leadership Tips for the Holidays

Ah, the holidays. Just hearing those two words can bring so much to mind, right? Cozy lights, laughter, that one coworker trying way too hard to win the office Secret Santa contest—it’s a vibe. But for leaders like you, the holidays can also feel like trying to juggle candy canes while riding a rollercoaster. 

Fun? Yes. A little stressful? Also yes.

Let me tell you about one holiday season that taught me a big lesson. It was late December a couple of years ago, and I wanted everything to be perfect. I’m talking about perfect-perfect. I wanted to keep our team motivated, get through year-end tasks without anyone burning out, and still somehow make the season feel special for everyone. No pressure!

In my head, I was thinking, “Okay, we’re going to crush this.” But by mid-December? Let’s just say the vibe wasn’t exactly jolly. Deadlines were piling up, people were feeling stretched, and I caught myself saying, “Let’s just survive this month,” way more often than I’d like to admit.

And that’s when it hit me: the holidays aren’t just something to “survive.” They’re an opportunity. An opportunity to show your team that you see them, you appreciate them, and you’re in this together. Sure, there are challenges—there always are—but the holidays are also a perfect excuse to create those feel-good moments that stick with people long after the decorations are packed away.

This blog isn’t about throwing a fancy office party (though, hey, go off if that’s your thing). It’s about leadership strategies that help you stay grounded, help your team stay motivated, and make the holidays memorable in the best way—for you and them. Because trust me, when the team feels good, the work gets done.

So, grab your peppermint mocha (or whatever festive drink is your jam), and let’s dive into how you can lead like a rockstar this holiday season.

Tips to Take Care of Your Team During the Holidays

The holidays at work can be a little chaotic. Deadlines don’t magically disappear, and customers or clients still need things done yesterday.

Meanwhile, your team is juggling work stress with holiday shopping lists, family drama, and figuring out how to bake cookies for their kid’s school party without burning the house down. (Yes, Susan, I’m talking about you and your “crispy” gingerbread last year.)

As a leader, this is your time to step up and make things easier for your team. The holidays aren’t just about hitting targets—they’re about showing your people that you see them and that their well-being actually matters.

Here’s how you do that:

1. Be Flexible with Schedules

Here’s the deal: the holidays are busy for everyone. People might need time off to travel, prep for family gatherings, or just breathe.

Be open to flexible schedules where possible. Maybe let them log in a little later or leave a little earlier. Trust me, that extra hour to grab a gift or beat the holiday traffic? It means a lot. And don’t forget—being flexible doesn’t mean being a pushover; it’s just good vibes and good leadership.

2. Celebrate, but Don’t Overdo It

We all love a good holiday celebration, but not everyone wants to be forced into a karaoke contest at 6 PM on a Thursday. (I’m looking at you, last year’s overzealous party planner.) Keep celebrations light and optional.

Maybe organize a small lunch or a gift swap that doesn’t break the bank. The goal is to bring people together, not stress them out more.

3. Check In on Their Mental Health

Let’s face it—this season can be overwhelming. Even the most cheerful folks can feel the pressure. Take a moment to check in with your team. Ask, “How’s everything going?” and mean it. If someone seems off, remind them it’s okay to take a breather. Sometimes, just knowing their boss cares can make a world of difference.

4. Be the Energy You Want to See

If you’re running around like a stressed-out elf, your team will feel that. Stay calm, stay positive, and lead by example. Throw in a little humor when things get hectic—because honestly, if we can’t laugh at the chaos, what’s the point?

The holidays don’t have to be a season of burnout. By being thoughtful, supportive, and human, you can help your team thrive—even with a million things going on. After all, happy team, happy holidays.

How Leaders Take Care of Themselves During the Festive Season

Okay, let’s talk about something leaders don’t always prioritize during the holidays: themselves. Yep, I said it. We spend so much time trying to keep everything running smoothly for the team, the business, and maybe even our own families that we forget about the person in the mirror. 

Being a leader during the holidays is kind of like being the captain of a ship in choppy waters. Everyone’s looking to you for direction, and if you’re running on empty, you can’t steer the ship. So, let’s ditch the “I’m fine, everything’s fine” routine and get real about how to actually take care of yourself.

1. Set Boundaries and Stick to Them

I get it. You want to be available. You want to help your team and make sure everything’s done. But here’s the truth: you’re not a 24/7 hotline. Decide when you’ll log off, and actually log off. Let your team know, “Hey, I’ll be unavailable after 6 PM, but I’m here if you need me during the day.” Setting boundaries is not selfish—it’s smart.

2. Take a Break (Yes, Really)

Leaders often feel guilty about stepping away, but guess what? You need breaks, too. Block off time to recharge, even if it’s just a quiet 20 minutes with your favorite holiday playlist and a cup of coffee. Or take a day off to do something you love—no work emails allowed. The holidays are about joy, and you deserve a little of that joy for yourself.

3. Say No Without Guilt

Can you be on every call, answer every email, and attend every holiday event? Nope. And that’s okay. Saying no doesn’t make you a bad leader; it makes you a human one. Trust your team to handle what they can, and let go of the idea that you have to do everything.

4. Lean on Your Support System

Whether it’s a mentor, a colleague, or your best friend, talk to someone. Leadership can feel lonely, especially during the holidays when everyone’s busy. Share what’s on your mind, ask for advice, or just vent. Sometimes, hearing “You’ve got this” from someone you trust can make all the difference.

5. Remember Why You’re Doing This

When things feel overwhelming, pause and think about what the holidays mean to you. Is it spending time with family? Wrapping up a great year? Creating a positive vibe for your team? Whatever it is, keep that “why” front and center. It’ll help you stay focused on what really matters.

At the end of the day, you’re not just a leader—you’re a person. And people need rest, joy, and a little grace during the holidays. So, take care of yourself because when you’re at your best, everyone around you benefits. 

Lead, Laugh, and Love the Holidays

And there you have it—your go-to guide for thriving as a leader during the holidays. From supporting your team with flexible schedules and thoughtful check-ins to taking care of yourself with boundaries and breaks, the festive season doesn’t have to be a juggling act where you’re one dropped ball away from disaster. Instead, it can be a time to bring out the best in your team and yourself.

Leadership during the holidays isn’t about being perfect. It’s about being present. It’s about showing up for your team in ways that matter while also giving yourself permission to enjoy the season. Yes, there will be challenges. Yes, things will get busy. But if you take the time to focus on people—your team, your family, and yes, YOU—you’ll look back on this season and feel good about how you handled it.

So, go ahead and sprinkle some holiday cheer, tackle those to-do lists with a smile, and don’t forget to recharge when you need it. Leadership is a gift, but so is your time and energy. The holidays only come around once a year—make them count for yourself and the people who count on you.