Your December Holiday HR Checklist: What Employers Should Prioritize Before the 2025 Year-End

Written By Alex Santos

The first week of December arrives fast — and with it comes a unique blend of holiday excitement, year-end deadlines, compliance updates, PTO requests, and the final push toward achieving annual goals. For business owners and HR teams, this season is joyful, yes, but also one of the busiest periods of the year.

A thoughtful, proactive holiday HR checklist helps keep your teams supported and your operations running smoothly. This guide walks through the most important items to tackle in early December, with an eye on compliance, communication, culture, and employee experience.

1. Finalize PTO & Holiday Scheduling (Before It Becomes a Fire Drill)

December is peak PTO season, and unclear expectations can create unnecessary tension or last-minute staffing issues. Use the first week of the month to:

Review Remaining PTO Balances and Policies

Employees may still be unsure about whether unused PTO carries over, expires, or can be cashed out. If you haven’t communicated your policy clearly, now is the time.

You can also link employees to internal self-service dashboards to reduce back-and-forth emails.

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Ensure Holiday Coverage Plans Are Finalized

Managers should confirm:

  • Who is “on” and who is “off”

  • Whether temporary reassignments are needed

  • What deadlines must be adjusted for December

Encourage managers to cross-train where possible to prevent bottlenecks.

2. Conduct a Quick Year-End Compliance Review

December is a meaningful checkpoint for compliance items that often get overlooked.

Verify I-9, Recordkeeping, and Documentation

With the updated form in circulation, complete an internal audit to ensure you’re compliant before January hits.

Resource you can share:

Understand New Laws Taking Effect January 1

Many states roll out labor law changes on Jan. 1 — including wage increases, non-compete rules, leave laws, and handbook requirements.

If you have Florida employees, check out a recent update below:

Now is also the perfect time to schedule your handbook refresh for Q1.

3. Wrap Up Benefits Administration & Open Enrollment Tasks

If your open enrollment ends in early December—or just wrapped up—use this week to finalize details.

Double-Check Enrollment Submissions

Ensure:

  • Every employee’s elections are accurate

  • Carriers have confirmed receipt

  • Payroll deductions align with chosen plans

A small mistake now can turn into a costly correction in January.

Review these helpful resources:

4. Plan a Culture Moment — Not Just a Holiday Party

Many employees crave connection and appreciation at the end of the year. The holiday season offers a great opportunity to reinforce culture intentionally.

Create an Inclusive Holiday Experience

Not everyone celebrates the same traditions. Companies can keep celebrations enjoyable and inclusive with:

  • Sensitive language in invites

  • Flexible participation options

  • Recognizing multiple cultural holidays

Show Appreciation in a Personal, Non-Performative Way

Whether it’s handwritten notes, small gifts, or creative recognition, meaningful appreciation goes a long way. Tie it back to your team’s measurable achievements.

More on this topic:

5. Start Your 2025 Planning Now

Many organizations wait until January to launch strategic HR planning, but December is ideal for setting up a smooth new year.

Review Hiring Pipeline Needs

Look at upcoming retirements, promotions, and anticipated growth.
We provide helpful tips on finding talent in our post How to Hire Better.

Evaluate Performance Metrics & Goal Setting

If your performance reviews happen in Q1, now is the time to confirm criteria and timelines. Consistency creates trust.

Check out:

Plan for Fractional HR Support if Needed

Many companies hit a seasonal dip or spike and need expert support to reset their HR structure. Here’s How Fractional HR Can Help You Scale if you’re an SMB owner or leader.

6. Reinforce Cybersecurity & AI Policies During Holiday Downtime

The holidays are a peak period for phishing, data breaches, and mis-use of AI tools.

Run a Quick AI & Security Reminder

Send a simple, clear message about:

  • Password hygiene

  • Email vigilance

  • Approved AI tools

  • How to report suspicious behavior

Related reading:

A Smoother December Starts with a Thoughtful Checklist

With the right planning, the first week of December can set the tone for a calm, compliant, culture-building holiday season. Focus on communication, clarity, and proactivity—and your team will feel supported during one of the busiest times of the year.

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  • Employers should focus on clear PTO planning, compliance updates, and year-end administrative tasks. December is also a great time to reinforce culture and ensure benefits and payroll changes are accurate. Prioritizing these areas reduces stress for both managers and employees.

  • Start by reviewing PTO requests early and setting expectations for coverage. Cross-training team members helps prevent operational slowdowns, and temporary support can fill unavoidable gaps. Transparent communication is the key to preventing last-minute surprises.

  • Most employers benefit from an annual review because new state and federal regulations often take effect on January 1. Even when laws don’t change, organizational policies may need adjustments to reflect updated practices or technologies. A yearly audit keeps policies consistent and defensible.

  • Offer optional participation and avoid centering events around a single tradition. Provide neutral language in invites and consider alternative ways to celebrate, such as team appreciation days or community service activities. Inclusivity helps everyone feel welcome and respected.

  • Common missteps include ignoring compliance deadlines, failing to confirm benefits enrollments, and not communicating PTO expectations. Businesses also sometimes underestimate the importance of employee appreciation and culture touch points. Addressing these areas proactively leads to smoother year-end operations.

Alex Santos
As Managing Member of Collabor8 Learning, my role is to build and execute learning and development strategies for organizations seeking to improve the return they are getting from their training programs. We focus on four core areas: performance analysis, instructional design, e-learning development, and learning management. As a hybrid HR/instructional design consultancy, Collabor8 Learning partners with your team to leverage today's training technologies to increase the productivity of your people. I am a senior human resources and training executive with over 17 years of progressive experience. My work in private industry has focused heavily on the development of learning and development systems that transform employee performance from ordinary, to remarkable. I accomplish this by combining organizational development strategies and tactics to blended learning programs with line of sight alignment to clearly defined performance goals. Additionally, I launched Miami Payroll Center in conjunction with my brother and sister-in-law in 2004 to meet the payroll needs of small to mid-size organizations. Our consultative approach to guiding new entrepreneurs as well as more seasoned business owners in alleviating the pain of payroll processing has created a very successful and growing payroll processor in the market. Specialties: Instructional Systems Design, E-Learning, Learning Management Systems, Payroll, Organizational Development, Employee engagement, HR Strategic Planning, Talent Acquisition & Management, Leadership Development, Coaching & Mentoring, Employment Branding Proposition & Positioning, Workforce Planning, Performance Management, and Leadership Development.
https://www.bynimble.com
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