As a high school principal, I remember many sleepless nights during the holiday season. The Stress of trying to balance staff morale, student behavior, and community needs often felt overwhelming. I worried about everything—how to support staff stretched thin by illness, how to keep students focused when their energy was through the roof, and how to ensure the families in our community who were struggling could still find joy in the season. I wanted to do it all, but the weight of those expectations sometimes left me staring at the ceiling, wondering if I was doing enough. Through those struggles, I learned that leading during the holidays isn’t about solving every problem—it’s about focusing on what matters most and bringing your team and community together to make an impact.

With that back drop, Here are four areas school leaders often wrestle with during the holidays and how you can address them without losing Sleep.

1. Addressing Student and Staff Well-Being

The holiday season can amplify stress and emotions, particularly for those facing financial hardship, family challenges, or Mental Health struggles. Ensuring the well-being of students and staff is critical.

What You Can Do:

• Create safe spaces for open dialogue, such as student support groups or staff wellness check-ins.
• Share mental health resources, like counseling services or local hotlines.
• Celebrate small wins by fostering gratitude and positivity through school-wide initiatives like kindness challenges or gratitude walls.

Communication Tip:
Be transparent about the resources available. Send out weekly updates to staff and families highlighting support opportunities, and consider hosting a virtual town hall to discuss mental health and well-being strategies.

2. Managing Increased Staff Absenteeism

As illnesses peak and stress levels rise, staff absences can become more frequent. This leaves administrators and remaining staff stretched thin.

What You Can Do:

• Develop a robust plan for substitute coverage and incentivize substitutes during peak times.
• Encourage self-care by reminding staff about wellness resources and offering flexibility in schedules where possible.
• Recognize the hard work of those stepping in to help, even with small gestures like providing breakfast or personalized thank-you notes.

Communication Tip:
Keep communication about absenteeism solutions positive and proactive. Instead of focusing on the challenges, highlight how the team is coming together and emphasize the importance of supporting one another.

3. Maintaining Student Engagement

With the holidays approaching, keeping students focused can feel like an uphill battle. Disruptions can increase, and energy levels may soar, leaving educators feeling overwhelmed.

What You Can Do:

• Integrate holiday-themed activities into the curriculum to maintain engagement while meeting learning objectives.
• Set clear expectations for behavior and reinforce them with positive incentives.
• Plan high-energy activities, like spirit weeks or themed assemblies, to channel excitement productively.

Communication Tip:
Use staff meetings and newsletters to share tips for maintaining engagement and behavior management. Acknowledge the challenges teachers face while celebrating their creativity in keeping students on track.

4. Supporting Families in Need

The holiday season can spotlight disparities within your school community, with some families struggling to meet basic needs. This can create additional stress for students and school leaders alike.

What You Can Do:

• Partner with local organizations to host holiday drives for food, clothing, and gifts.
• Connect families with community resources such as food banks or counseling services.
• Ensure dignity and discretion by creating systems for families to access support without stigma.

Communication Tip:
Frame these initiatives as opportunities to build community rather than addressing deficits. Use newsletters, social media, and personal outreach to highlight the generosity and collaboration of your school community.

Bringing It All Together

The holiday season can feel overwhelming, but it’s also a powerful opportunity to foster connection, care, and resilience in your school community. By addressing well-being, absenteeism, engagement, and family needs proactively—and communicating your plans effectively—you can lead with empathy and Clarity.

Remember, your communication is the thread that ties these efforts together. When staff and families understand the why behind your initiatives and feel involved in the solutions, your community becomes stronger. Use positivity, transparency, and frequent updates to show everyone that you’re navigating these challenges together.

How will you lead your school community through this holiday season? Let’s start the conversation.

Ready to take your leadership to the next level? My new course, Take Control of Your Leadership, is designed to help school leaders overcome overwhelm, build strong cultures, and stay focused on what truly matters. Don’t wait—start your journey today!

Darrin Peppard Dr. Darrin Peppard

Dr. Darrin Peppard is an author, leadership coach, consultant, and speaker focused on organizational culture and climate, and growing emerging leaders. Darrin is the best-selling author of the book Road to Awesome, and is the host of the Leaning into Leadership podcast. As a ‘recovering high school principal’, Darrin shares strategies and lessons learned from 26 years in public education to help leaders gain clarity, find joy in their work, and walk in their purpose.