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Cultivating Holiday Leadership Skills For Year-Round Success

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The holiday season is a time of celebration and connection. For leaders, however, it can also be challenging, filled with competing priorities, end-of-year deadlines and heightened emotional dynamics among teams. Yet, within these challenges lies an opportunity to cultivate vital leadership skills that can positively impact teams beyond the holiday season.

Holiday leadership isn’t just about navigating the chaos of December; it’s about leading with intentionality and adaptability during one of the most dynamic times of the year. It is possible for leaders to develop holiday-specific leadership skills that set their teams up for long-term success.

“During the holidays,” states Alison Godfrey, an executive leadership coach, “clear communication and expectation setting is very important. It’s a time when work and personal life boundary-setting becomes critical. It’s a time when boosting morale, showing deep gratitude and appreciation and celebrating achievements are important.”

Cultivating Emotional Intelligence

The holidays often evoke a range of emotions. Leaders must tune into their teams’ emotional landscapes and demonstrate heightened emotional intelligence. During the holidays, this means recognizing signs of burnout, tactfully addressing interpersonal conflicts and creating an inclusive environment for diverse celebrations and traditions.

Leaders can practice active listening and open communication by checking in with team members regularly. A quick “How are you feeling about balancing work and holiday commitments?” can go a long way in showing empathy and support.

Prioritizing People Over Productivity

While end-of-year goals are important, leaders who focus solely on deliverables risk alienating their teams. The holidays are a time to emphasize the human element of leadership. Taking a people-first approach, such as offering flexible schedules, signals that leaders value their teams’ well-being.

This doesn’t mean sacrificing productivity but balancing it with recognizing employees’ need for time with their families and personal priorities. The payoff is a more loyal and motivated workforce that feels genuinely cared for, even during high-stress periods.

Strengthening Adaptability

Holiday disruptions—unexpected absences, supply chain delays or fluctuating customer demands—test a leader’s ability to adapt. The ability to remain calm and pivot effectively in uncertainty is a hallmark of great leadership.

To develop this skill, practice proactive problem-solving and maintain open lines of communication. Sharing contingency plans with teams ensures everyone is aligned and prepared for potential curveballs.

Strengthening Gratitude

The holiday season is a natural time to express gratitude. Public acknowledgments, personalized thank-you notes or small tokens of appreciation make employees feel valued. Recognition should extend beyond accomplishments to include behaviors that align with company values, such as collaboration, innovation or resilience.

Why Holiday Leadership Skills Matter

Developing leadership skills during the holidays isn’t just a seasonal exercise—it’s an investment in long-term growth:

  • Improved team morale: Teams that feel supported and appreciated during the holidays are more likely to stay engaged and motivated in the new year.
  • Enhanced retention: Employees who experience empathetic and inclusive leadership are less likely to seek opportunities elsewhere, even in competitive job markets.
  • Crisis management readiness: The adaptability and emotional intelligence leaders develop during the holidays prepare them for other high-pressure periods throughout the year.
  • Stronger relationships: Prioritizing people and fostering inclusivity deepen trust and camaraderie within teams, leading to higher levels of collaboration.

Practical Strategies For Leaders

To implement these principles, leaders can take actionable steps such as:

  • Hosting end-of-year town halls to celebrate milestones and share future goals.
  • Encourage employees to take time off and model this behavior by taking breaks themselves.
  • Offering flexible deadlines and adjusting workloads to accommodate holiday demands.
  • Soliciting feedback on holiday policies and events to ensure they align with team needs.

“People’s emotional bank accounts at home are often overdrawn in quarter four,” explains Devin Marks, president of Connect To Compel. “Downshifting work hours to accommodate after-hours pressures is a bonus holiday gift.”

Adopting a holiday leadership style strengthens teams and positions leaders as role models who inspire and motivate long after the decorations are down. Leadership during the holidays is a test of skill and a testament to character.

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