Holiday Leadership to Motivates & Set the Stage for a Strong New Year

As the year winds down, most employers look for ways to say “thank you,” whether through holiday gatherings, year-end messages, or rewards such as gift cards. But today’s most effective leaders are going beyond traditional appreciation to use the holiday season as a strategic bridge into the new year.

The final weeks of the year bring both celebration and pressure. According to the Society for Human Resource Management (SHRM), 53% of workers report feeling stressed during the holidays, 41% say holiday stress reduces productivity, and 22% experience a dip in emotional well-being. In other words: employees need thoughtful, steady leadership now more than ever.

Done well, holiday recognition can restore energy, strengthen culture, and create momentum that carries into January. Below are six practical leadership practices—grounded in recent insights from Monday.com—that help organizations support teams during a demanding season while setting up a confident, motivated start to the new year.

1. Create Clarity Early

Holiday stress is often tied to uncertainty. Employees are juggling childcare, travel, school events, and financial pressures—so unclear year-end expectations can significantly amplify anxiety.

Give teams a clear roadmap of what must be finished by year-end and who owns what. Early clarity prevents last-minute scrambles, strengthens trust, and gives people space to plan. When the path is clear, your recognition efforts feel earned, not rushed.

2. Offer Flexibility Without Lowering Standards

Flexibility is a leadership skill. Allow employees to adjust their schedules, coordinate coverage through shared calendars, or shift work blocks around family commitments.

This flexibility doesn’t diminish performance—it makes it possible.

Teams who feel trusted are more likely to stay invested, take ownership, and bring their best energy into the new year.

3. Lead With Emotional Awareness

Holiday experiences vary widely. Some employees may be energized and festive. Others may feel overwhelmed, lonely, or emotionally strained.

Avoid assumptions about holiday plans and instead use supportive, open-ended prompts:

• “I hope you’re able to get some rest this season.”
• “What support would help you most this month?”

This approach respects personal boundaries while showing you genuinely care.

4. Model Healthy Boundaries

Even the best recognition program won’t resonate if employees feel tethered to work during the holidays. Leaders set the tone.

Be intentional about:

• Avoiding late-night messages
• Scheduling communications for business hours
• Setting team quiet hours
• Encouraging actual time off

Rested employees return in January with greater clarity, creativity, and motivation.

5. Deliver Specific, Personal Gratitude

Generic thanks—“Thanks for your hard work!”—rarely land with impact. Specific, personal recognition is one of the pillars of effective employee recognition to build confidence and deepen engagement.

Examples:

• “Your attention to detail strengthened every client handoff this year.”
• “Your mentorship helped our new hires ramp faster than expected.”

Thoughtful appreciation reinforces what great work looks like and boosts morale at a time when employees need it most.

6. Create Space for a Reset, Not Just a Rush

Yes, December is busy; but it’s also a perfect moment to reflect as a team. Hold a short retrospective and ask:

• What worked well this year?
• What slowed us down?
• What should we do more of next year?

This sense of shared progress helps employees close the year with pride and begin the next with clarity and momentum.

Strengthening Your Holiday Recognition with Meaningful Rewards

While leadership behaviors set the tone, meaningful rewards reinforce your gratitude. Gift cards—especially flexible, choice-driven options—remain one of the most appreciated forms of recognition across industries. They allow employees to choose what matters most to them, whether it's groceries for holiday meals, self-care essentials, or something that sparks joy.

Through the Engage2Reward™ Gift Card Ordering Platform, organizations can:

• Send personalized rewards at scale
• Deliver digital or physical cards instantly
• Track distribution with built-in reporting
• Offer the flexible Engage2Reward™ Choice Card, giving recipients the opportunity to select their preferred gift card reward from hundreds of popular brands.

A thoughtful reward paired with thoughtful leadership helps employees feel seen, valued, and confident heading into a new year.

Final Thought

Holiday recognition isn’t just about closing the year with appreciation; it’s a leadership opportunity to set the emotional and cultural foundation for the year ahead. When leaders provide clarity, flexibility, empathy, boundaries, and meaningful appreciation, teams start January not depleted, but energized.

A motivated team in December becomes a high-performing team in January.

Schedule a call with our team today to learn how the Engage2Reward Platform can start your team off on the right foot this new year.