The end-of-year holiday season means festive lights, team lunches, and a general sense of winding down. That is, for everyone except HR professionals.
For you, the "most wonderful time of the year" is a chaotic sprint to the finish line. You're juggling a tidal wave of time-off requests, finalizing year-end reviews, planning the company party, and managing a workforce that's stressed, excited, and distracted all at once.
This is your essential survival guide. We've broken down the chaos into a strategic framework covering administration, culture, and wellness. Follow this approach and you'll achieve a smoother, compliant, and more joyful holiday season for you and your entire team.
The Administrative Checklist
Before you can get to the fun stuff, you need to lock down the fundamentals. Clear policies and early communication are your best defense against holiday-related confusion and administrative headaches.
Managing Holiday Time-Off Requests
The first wave to hit your desk is always PTO requests. Everyone wants the same days off, and managers are suddenly worried about coverage. Balancing employee requests with operational needs is a difficult tightrope walk, and a perceived lack of fairness can quickly damage morale.
Your holiday leave policy needs to be your single source of truth. A clear, well-communicated policy reduces conflicts, ensures departments have the staff they need, and makes the process feel fair. This builds trust and prevents last-minute scrambles. If you don't have one, or if yours is vague, start here:
Communicate early. In early November, send a company-wide reminder of the policy.
Clarify the process. Is it first-come, first-served? Does seniority play a role? Is it a lottery system for high-demand days? Be transparent about how decisions are made.
Set a deadline. Establish a clear "request by" date for major holiday periods (Thanksgiving, Christmas, New Year's). This gives managers time to build coverage schedules.
Use a central system. Encourage managers and employees to use your HRIS or a shared calendar. Avoid managing requests through scattered emails and Slack messages.
Clarifying Holiday Pay and Policies
Once time off is settled, the next question is inevitably: "Which days do we get paid for?" Confusion around holiday pay, especially for part-time, temporary, or non-exempt employees, leads to frustration and payroll errors. Clear and proactive communication ensures legal compliance, reduces payroll questions, and makes employees feel they're being compensated correctly.
List the dates. Send a simple memo or email listing the specific dates your company recognizes as paid holidays.
Know the law. The Fair Labor Standards Act (FLSA) doesn't require private employers to provide paid holidays, though most companies offer them as a standard benefit. For non-exempt (hourly) employees, if they work on a holiday, they must be paid for that time (plus any overtime, if applicable).
Check state laws. Some states, like Massachusetts and Rhode Island, have specific rules about work on certain holidays.
Finalizing Year-End Performance Reviews
Nothing says "happy holidays" like chasing down a manager for an overdue performance review. Trying to get meaningful, thoughtful reviews completed in December is nearly impossible. Employees are distracted and managers are rushed, turning a valuable process into a check-the-box exercise.
When you get ahead of this timeline, you get meaningful feedback on record, employees feel properly recognized, and you're not chasing paperwork on December 23rd. Everyone starts the new year fresh. To accomplish this, decouple the process from the holiday rush:
Start earlier. Kick off the year-end review process in the fall. Set deadlines for self-assessments and manager reviews in mid-November, before the Thanksgiving break.
Focus on conversation. Encourage managers to hold review conversations in early December, positioning them as a way to celebrate the year's wins and set exciting goals for the new year. Consider this in your overall continuous feedback strategy.
Separate pay from performance. If possible, separate the performance review conversation from the compensation or bonus conversation. Forbes reported this lowers stress on both sides and leads to more honest feedback.
The Culture and Morale Playbook
With the admin under control, you can shift focus to what truly makes the season special: your people. This is your chance to actively shape company culture and end the year on a high note.
Planning an Inclusive Holiday Party
The company holiday party is often the biggest culture-building (or breaking) event of the year. Planning an event that's fun, safe, and genuinely inclusive for a diverse workforce is a challenge. After years of virtual events, employees crave connection, but not everyone drinks alcohol or feels comfortable in a loud party setting.
Think "connection" instead of just "party." A well-planned, inclusive event makes employees feel genuinely valued. It's a powerful tool for building cross-departmental relationships and boosting morale, which directly impacts retention. Here’s how to make sure you keep inclusivity in mind:
Survey your team. Don't guess what people want. Send a simple poll: "What kind of year-end celebration would you enjoy most?"
Consider inclusive formats:
Daytime event: A catered lunch or brunch during work hours is more family-friendly and takes the pressure off evening commitments.
Activity-based: Try a team-building activity like a cooking class, escape room, or company-wide volunteer day.
The classic party (with a twist): If you go for an evening event, offer plenty of non-alcoholic craft beverages, feature food that meets all dietary needs, and pick an accessible venue.
Promote safety. If alcohol is served, be a responsible host. Use a drink ticket system, provide ride-share vouchers, and remind managers they're still leaders at the event.
Fostering Inclusive Celebrations
The "holiday season" means different things to different people. When a company defaults to a "Merry Christmas" approach, it can unintentionally make employees who celebrate Hanukkah, Kwanzaa, Diwali, Bodhi Day, or nothing at all feel excluded.
An inclusive environment makes all employees feel a sense of belonging which is a cornerstone of positive workplace culture and a key driver of engagement. Adopt a "season of celebration" mindset to accomplish this:
Secular decor. Opt for neutral, seasonal decorations like snowflakes, winter scenes, or festive lights rather than specific religious symbols.
Multi-cultural awareness. SHRM recommends sharing a multi-cultural holiday calendar in your company newsletter to build awareness.
Offer floating holidays. This is one of the most effective ways to be inclusive. By providing one or two floating holidays, employees can choose to take time off for the days that are most meaningful to them.
Showing Genuine Appreciation
After a long year, a simple "thank you" goes a long way. A generic email blast, however, does not. Employees are tired. If their hard work isn't recognized, they end the year feeling depleted and unvalued, leading them to browse job boards in January.
According to Gallup, employees who don't feel adequately recognized are twice as likely to say they'll quit in the next year. Genuine recognition is one of the most powerful and cost-effective retention tools you have. It validates an employee's contribution, improves loyalty, and ends the year on a high note. Get specific and personal:
Personalized notes. Ask leaders and managers to write specific thank-you notes (handwritten or digital) to their team members, calling out a real contribution from the past year.
The gift of time. Close the office an hour or two early on the Friday before a holiday, or give an extra "recharge" day off.
Small, thoughtful gifts. A gift card for coffee, a book, or a meal delivery service goes a long way.
Wellness stipend. Offer a small stipend for employees to use on a wellness app, gym class, or massage.
The Wellness Check-in
Remember that HR is the heart of the company. That means monitoring the organization's health and your own.
Addressing Holiday Stress
For many, the holidays bring significant personal stress from finances, family obligations, and travel. This stress doesn't disappear when they log on for work. Stressed, distracted, and burned-out employees lead to lower productivity, more sick days, and a general dip in morale.
Be a resource, not another source of stress:
Acknowledge it. Send out a communication that acknowledges the holidays can be tough and reminds employees of the mental health resources available to them.
Promote your EAP. This is the perfect time to remind everyone about your Employee Assistance Program or other mental health benefits. A simple, accessible platform like Bennie puts easy access to EAPs, virtual therapy, and wellness apps right at your employees' fingertips.
Encourage PTO. Actively encourage managers to support their teams in using vacation time. A culture that shames taking breaks is a recipe for burnout.
Prioritize ruthlessly. Work with leadership to agree on what must be done by December 31st and what can wait until January.
A supportive approach builds psychological safety. It shows you care about your employees as whole people, not just workers, which fosters long-term loyalty and a healthier, more resilient workforce.
A Note for You, the HR Professional
You spend the entire season taking care of everyone else. Who is taking care of you? HR professionals are at extremely high risk of burnout because they absorb the stress of the entire organization.
Put your own oxygen mask on first:
Block your calendar. Schedule your own PTO and commit to it.
Delegate. Create a volunteer "holiday committee" to help with logistics. You don't have to plan the festivities alone.
Set boundaries. When you're off, be off. Turn off the notifications. The payroll issue can (almost always) wait until you're back.
You'll avoid burnout, enjoy your own holiday, and return in the new year with the energy you need to lead.
Your Key to a Successful Holiday Season
The secret to a successful holiday season in HR isn't magic. It's a three-part formula: proactive planning (getting the admin done early), thoughtful communication (making people feel included), and genuine care (focusing on wellness). By tackling the administrative hurdles early, you free yourself up to focus on what truly matters: your people.
At Bennie, we make benefits and HR simpler so you can do just that. A smooth, well-run benefits platform gives you back the time you need to be the strategic, culture-building leader your company deserves.
Here's to celebrating the hard work of the past year and looking forward to a bright and successful new one.
