Not Everyone Has a “Happy Holiday” Coming up: A Leader’s Guide to Holiday Sensitivity

I learned this lesson back in college, during what is usually a celebratory time of year; holiday break. Finals were over, no homework was due, and the campus echoed with cheers of “Happy Holidays!” and “See you next year!” But beneath the festive facade, I realized a harder truth.

On the last day of the semester, while most students rushed home, I noticed several staying behind. When I asked why, their answers hit me hard: Some had no home to return to. Others dreaded going home because it meant facing horrible, or even abusive, family dynamics. International students were also thousands of miles away and couldn’t go home.

On a college campus, it was very obvious to see who went home and who stayed. But take that same concept and bring it into the career working world, and the same challenges exist, they just aren’t as visible. 

According to a study on Monster.com “More than half of workers (53%) say they feel more stressed than usual during the winter holidays, and about 1 in 5 (22%) say their overall well-being declines.”

Behind every “Have a great holiday break!” in our workplaces, there are team members: 

  • Living alone in a new city, far from family
  • Dealing with complex, or horrible, family situations
  • Unable to afford travel home
  • Working through the holidays to support others
  • Managing cultural differences in holiday celebrations

If that’s not enough, The American Psychiatric Association reported that 47% of service/retail workers and 54% of healthcare workers say their stress level increases during the holiday season.

This reality calls for a deeper level of Employee Engagement and authentic Company Culture. As leaders, we can create a Culture of Connection™ during the holiday season by:

  1. Asking thoughtful questions beyond the standard “What are your holiday plans?”
  2. Organizing inclusive celebrations that acknowledge diverse traditions
  3. Creating support systems for team members staying local
  4. Offering flexible work arrangements for those managing holiday stress
  5. Connecting team members who might be spending the holidays alone

Try this: Instead of the casual “Happy Holidays!” start a real conversation. “Do you have any special plans? Would you like to join our holiday dinner? Need any support during the break?” These simple questions could make a world of difference for someone struggling with the season.

The truth is, building a thriving workplace isn’t just about productivity metrics and quarterly goals. It’s about creating a space where every team member feels seen, supported, and connected—especially during times when loneliness and stress run high. When leaders take the initiative to foster genuine connections during the holiday season, they’re not just being nice—they’re laying the foundation for a more engaged, loyal, and resilient team that will thrive long after the decorations come down.

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