The end of the year is here—Thanksgiving has passed and now the final countdown is on. Whether you celebrate Hanukkah, Christmas, Kwanzaa, New Year’s, or simply revel in the crisp air and falling snow, it’s officially Holiday Season.
Over the years, I’ve worked in a variety of places. Some created a fun, festive environment where people truly looked forward to the season. Others didn’t—making the holidays feel less joyful, even a little empty. The difference always came down to one thing: culture.
Early in my career, I worked for a non-planning micro-manager who walked in each morning with whatever was top of mind, treating every request like an emergency. We hustled to keep up, even more so during the holidays, never sure if the supervisor would even show up. It taught me first-hand how quickly a lack of leadership and celebration can drain joy from a team.
Those years shaped my philosophy: culture isn’t something that just “happens”—it’s a series of choices. Here’s what I practice (and recommend to you) for making the holidays—and every season—special at work:
1. Gratitude
Don’t just feel gratitude, express it specifically and often.
A simple “Thank you, Joe, for setting up all the lighting for tonight’s event” makes a bigger impact than generic praise. Specific appreciation builds trust and warmth, not just at the holidays, but all year long.
2. Relationships
Get to know your people and honor what matters to them.
Find out which holidays, celebrations, or days are important to your coworkers. Celebrate together, or simply acknowledge their special days—whether that’s saying “Happy Hanukkah” or bringing in a treat for Administrative Professionals Day. Small gestures create lasting bonds.
3. Culture (Fast & Slow)
Culture thrives in both busy and slow seasons—if you invest in it intentionally.
If things are busy, inject moments of fun with your coworkers as you serve others. That’s the secret to building a great culture, even under pressure. If things are slow, seize the opportunity for a team lunch or a non-work conversation. Both build a sense of belonging that outlasts the season.
4. Preparation
Preparation isn’t just logistics—it’s the foundation of team confidence and freedom. By now, plans for the new year should already be in motion—setting meetings, preparing registrations, buying supplies, and creating calendars. Preparation breeds the confidence that allows your team to relax and enjoy the holidays, knowing they’re ready for what’s next.
Behavior Drivers:
- Thank at least one team member by name and for something specific this week.
- Ask a coworker about an upcoming celebration or special day and acknowledge it.
- Whether it’s a lunch or a five-minute “holiday huddle,” create a micro-moment of connection before the year ends.
- Review your plans for Q1 with your team so everyone feels prepared and confident.
Over the years, these four practices have allowed me (and my teams) to build systems that create freedom for everyone. We all deserve to have fun at work—and as leaders, it’s our job to shape a culture that makes joy possible, no matter the calendar.
You’re not alone on this journey. If you want support building the culture you’ve been dreaming about, visit www.jasonchadock.com. Let’s make this season—and every season—the best it can be.
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