Keeping Your Team Engaged Through the Holiday Season: A Guide for Managers
The period between Thanksgiving and New Year's Day presents unique challenges for organizational leaders. While the holiday season brings celebration and time with loved ones, it also introduces potential disruptions to productivity, team cohesion, and employee engagement. For managers who want to maintain momentum and set their teams up for success in the coming year, navigating this delicate balance requires intentionality and strategic thinking.
Understanding Holiday Season Dynamics
The holiday season affects every workplace differently, but certain patterns emerge consistently across industries. Energy levels fluctuate as team members juggle professional responsibilities with personal commitments. Attention becomes divided between year-end deliverables and holiday planning. Stress levels often rise due to compressed timelines, budget concerns, and the pressure to close out the year strong while managing seasonal obligations.
In mortgage and financial services, the end of the year can bring a surge of clients wanting to close transactions before December 31st for tax purposes, creating intense pressure precisely when team capacity may be reduced. Technology and IT departments face their own challenges, balancing the need to complete projects before year-end with reduced coverage as team members take time off. Administrative professionals across all sectors find themselves managing holiday schedules, year-end reporting, and office celebrations while maintaining regular operational excellence.
Understanding these dynamics is the first step toward managing them effectively. Rather than fighting against the natural ebb and flow of the season, successful managers acknowledge these realities and plan accordingly.
Communication as the Foundation
Clear, proactive communication becomes even more critical during the holiday season. Team members need to understand expectations, deadlines, and priorities with greater precision than usual. When someone will be out of the office for a week, there's no room for ambiguity about what needs to be completed beforehand and who will handle various responsibilities in their absence.
Start by establishing a transparent time-off policy early in the season. Make sure everyone understands the process for requesting time off, how coverage will be handled, and any blackout dates that apply to your organization. This clarity reduces anxiety and allows team members to plan their personal time with confidence.
Regular check-ins take on added importance during this period. Brief daily or weekly touchpoints help managers stay aware of workload distribution, identify potential burnout before it becomes critical, and ensure that no one feels isolated or overwhelmed. These conversations also provide opportunities to recognize individual contributions and reinforce that each team member's work matters, even during a busy, distracted season.
Workload Management and Realistic Expectations
One of the most common mistakes managers make during the holidays is maintaining the same performance expectations they hold during other times of the year, despite reduced capacity and increased demands on team members' time and energy. This approach inevitably leads to stress, resentment, and decreased engagement.
Instead, take a realistic inventory of your team's capacity during this period. If you know that half your team will be taking time off during the last two weeks of December, plan accordingly. This might mean adjusting project timelines, identifying which initiatives can wait until January, or bringing in temporary support for critical functions.
Prioritization becomes essential. Work with your team to identify the truly critical deliverables that must be completed before year-end versus those that can be pushed into Q1 without significant consequences. This exercise often reveals that fewer things are genuinely urgent than we initially believe, and it demonstrates to your team that you value their well-being alongside organizational objectives.
For roles that require consistent coverage, such as customer service or technical support, develop a clear rotation schedule well in advance. Ensure that coverage responsibilities are distributed equitably and that everyone has the opportunity to take some time off during the season. The team member who volunteers to work Christmas might appreciate having New Year's off, and vice versa.
Recognition and Appreciation
The holiday season provides a natural opportunity to express genuine appreciation for your team's contributions throughout the year. However, effective recognition goes beyond generic holiday parties and gift cards. While these gestures have their place, the most meaningful recognition is specific, sincere, and personalized.
Take time to acknowledge individual achievements and growth you've observed over the past year. A handwritten note detailing specific contributions and their impact can mean more than any material gift. For team members who've gone above and beyond, consider year-end bonuses or additional time off as tangible expressions of gratitude.
Public recognition also matters. Whether in team meetings, company-wide communications, or informal gatherings, highlighting individual and team accomplishments reinforces that good work is noticed and valued. This is particularly important in administrative and support roles, where contributions may be less visible but equally essential to organizational success.
Creating Meaningful Holiday Traditions
Holiday celebrations should bring your team together rather than adding to their stress. The key is creating traditions that feel authentic to your organizational culture rather than forcing obligatory festivities that nobody genuinely enjoys.
Consider involving your team in planning holiday activities. What would they actually find meaningful or enjoyable? Some teams might appreciate a catered lunch and early dismissal. Others might prefer a voluntary after-hours gathering at a restaurant. Still others might value the flexibility to skip organized celebrations entirely in favor of additional time with their families.
For distributed or remote teams, virtual celebrations can still create connection. A brief online gathering where team members share a favorite holiday tradition, recipe, or memory can feel more genuine than an elaborate virtual party. The goal is human connection, not production value.
Flexibility as a Gift
Perhaps the most valuable thing you can offer your team during the holiday season is flexibility. When possible, allow team members to adjust their schedules to accommodate personal commitments. Someone might appreciate the ability to work from home on days when their children are out of school. Another team member might want to leave early one day to attend a holiday concert, making up the time elsewhere in the week.
This flexibility demonstrates trust and acknowledges that your team members have rich, full lives outside of work. The goodwill generated by these accommodations typically results in increased loyalty and engagement that extends well beyond the holiday season.
However, flexibility must be balanced with operational needs and fairness. Make sure that accommodation for one team member doesn't create unreasonable burdens for others. Transparent communication about how decisions are made and ensuring everyone has access to similar flexibility helps prevent resentment.
Preparing for the New Year
While managing the present is crucial, the holiday season also offers an opportunity to set your team up for success in the coming year. Use this time for reflection and planning, but do so in a way that energizes rather than overwhelms.
Consider scheduling brief one-on-one conversations with team members about their professional goals for the new year. What skills do they want to develop? What projects excite them? How can you support their growth? These conversations demonstrate investment in individual development and help you align team strengths with organizational needs in Q1.
Review the team structure and identify any gaps to be addressed through new hires in the new year. If you've been understaffed or have anticipated turnover, the holiday season is an excellent time to partner with recruiting specialists who can begin identifying candidates so you're ready to move quickly in January.
Supporting Mental Health and Well-Being
The holidays, despite their festive reputation, can be a difficult time for many people. Financial stress, family complications, grief over lost loved ones, and seasonal affective disorder all impact team members' well-being during this period. As a manager, you don't need to become a therapist, but you do need to create an environment where people feel safe acknowledging when they're struggling.
Make sure your team knows about available mental health resources, such as employee assistance programs, health insurance benefits, or other support services. Normalize conversations about stress management and self-care. Model healthy boundaries by taking time off yourself and disconnecting from work email during non-working hours.
Watch for signs that someone may be struggling more than usual—changes in performance, withdrawal from social interactions, or expressions of hopelessness. When you notice these signs, approach the individual with genuine concern rather than criticism and connect them with appropriate resources.
The Manager's Role in Setting the Tone
Ultimately, how your team experiences the holiday season largely depends on the tone you set as their manager. If you're stressed, overwhelmed, and treating every deadline as a crisis, your team will mirror that energy. If you approach this period with realistic expectations, genuine appreciation, and a balanced perspective, your team is more likely to remain engaged and positive.
This doesn't mean pretending that challenges don't exist or that workloads aren't demanding. It means acknowledging difficulties while maintaining focus on what matters most, your team's well-being and sustainable performance that will carry forward into the new year.
The holiday season will come and go, but the culture you create during this period and the relationships you strengthen will impact your team's engagement and performance for months to come. By approaching this season with intentionality, empathy, and strategic thinking, you can help your team not just survive the holidays but finish the year strong and enter January with renewed energy and commitment.
At Talent Core Solutions, we understand that even the best managers sometimes need additional support during peak seasons. Whether you're looking for temporary administrative help to manage holiday workload spikes or planning strategic hires for the new year, our specialized expertise in mortgage, IT, and administrative staffing can help you maintain team stability and set the foundation for continued growth.
