The holiday period exposes leadership.
For some organizations, the pace slows. For others, it accelerates. Deadlines don’t disappear, customers still need answers, and systems don’t pause just because the calendar does. At the same time, people are carrying more than usual—family obligations, financial pressure, travel, grief, and fatigue that doesn’t show up on a dashboard.
This is when leadership is felt most clearly.
Your team watches what you do far more closely than what you say. How available you are. How you handle pressure. What you tolerate. What you protect. The standards you quietly reinforce now will shape how your team enters the new year.
Great leaders use the holiday period to strengthen trust, reduce friction, and set conditions for momentum—not to extract a final surge of output from already stretched people.
Here’s what they consistently do differently.
1. They Protect Rest by Setting Clear Boundaries
Ambiguity is exhausting. When people don’t know what truly matters, everything feels urgent. During the holidays, that confusion compounds stress and drives unnecessary burnout.
Strong leaders remove the guesswork.
They clearly define what requires immediate attention and what can wait. They set expectations around response times. They establish coverage. And they communicate it early—before people start filling the gaps with assumptions.
Just as importantly, they model the behavior themselves.
If you answer emails late at night, your team will feel pressure to respond no matter what you say about balance. If you jump into every issue, you teach people that nothing can move without you. If you never truly disconnect, neither will they.
Boundaries aren’t about doing less. They’re about protecting judgment, focus, and energy when it matters most.
Leader actions:
- Publish a short holiday operating rhythm outlining response times, coverage, and urgency criteria
- Explicitly state what can wait—and reinforce it with your behavior
- Avoid after-hours messaging unless it genuinely meets the urgency threshold
- Intervene early when you see fake urgency or off-hours work creeping in
2. They Lead with Compassion by Giving the Gift of Time
The holidays amplify whatever people are already carrying. Stress hits harder. Energy fluctuates. Personal challenges surface more easily.
Great leaders don’t ignore this reality. They plan for it.
Compassion at the senior level isn’t about lowering standards. It’s about understanding that sustained performance requires margin. Leaders who fail to account for human strain may get short-term compliance, but they lose trust—and eventually people.
High-performing leaders watch for early signs of overload. A reliable contributor going quiet. Someone consistently pushing late. A subtle shift in engagement. When they see it, they step in early.
Sometimes that intervention is simple:
“Take the afternoon.”
“This can wait.”
“You don’t need to carry this tonight.”
Those moments are remembered long after the holidays end.
Leader actions:
- Proactively offer time off or lighter days when sustained effort is visible
- Ask in one-on-ones what would make the week more manageable—and act on it
- Adjust priorities or redistribute work when personal strain is clear
- Normalize taking time without guilt or justification
3. They Celebrate Inclusively and Intentionally
Not everyone experiences the holiday season the same way. Some people celebrate. Some observe quietly. Some struggle through it.
Strong leaders are aware of this without making it awkward or performative.
They acknowledge the season broadly and respectfully, without assuming what matters to people. They create space for team members to share what’s meaningful to them—if they choose—without pressure or spotlighting.
They also use this time to strengthen relationships beyond their usual circle.
A brief message. A thoughtful note. A simple check-in. These small, consistent gestures reinforce connection and belonging far more effectively than large, symbolic events.
Leader actions:
- Acknowledge the season in a way that respects diverse experiences
- Invite optional team sharing around what matters to people this time of year
- Reach out weekly to someone you don’t regularly interact with
- Keep gestures simple, personal, and sincere
4. They Run Empathy-Focused Check-Ins, Especially with Remote Teams
As routines shift, uncertainty increases. For remote and hybrid teams, the holidays can quietly magnify isolation, misinterpretation, and unnecessary anxiety.
Strong leaders counter this with presence and clarity.
They keep one-on-ones consistent. They don’t cancel connection in the name of busyness. And they resist turning check-ins into transactional status updates.
Instead, they ask questions that ground people and surface issues early:
What worked?
What didn’t?
What should we recognize?
What can be dropped?
They also stay alert to warning signs—self-doubt, information hoarding, heightened sensitivity, visible stress—and respond with transparency and access rather than control.
Leader actions:
- Maintain consistent one-on-one check-ins through the holidays
- Use reflective prompts instead of task-only updates
- Address uncertainty directly rather than letting assumptions grow
- Make it safe to be offline by ensuring work can continue without constant availability
5. They Close the Year by Looking Forward, Not Just Back
Most leaders spend December reviewing what happened. Metrics. Results. Lessons learned.
Great leaders also help their people understand what comes next.
As the year ends, teams want direction. They want context. They want to know where the organization is heading and why their work still matters.
Strong leaders provide a clear, forward-looking narrative. Not a long strategy deck—just a simple story about what’s being built in the coming months, why it matters, and how success will be measured.
They anchor debate and decision-making around the desired outcome. This shifts energy from problem-focused frustration to solution ownership.
They also model renewal. They share how they are resetting themselves—without preaching—then invite others to reflect on what they need to change heading into the new year.
Leader actions:
- Share a concise view of priorities for the next few months
- Frame decisions around the end state, not habits or preferences
- Model personal reset behaviors rather than prescribing them
- Ask your team what’s working for them—and what isn’t
Final Thought
Leadership during the holidays isn’t about pushing harder. It’s about leading cleaner.
Your people may forget the details of year-end meetings, but they will remember how you showed up—and how you made space for them to show up too.
That memory becomes the standard they carry into the new year.
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