Your December Holiday HR Checklist: What Employers Should Prioritize Before the 2025 Year-End
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.
Related Reading:
How to Craft a Job Offer That Top Candidates Can’t Resist (reinforces the importance of policies and clarity)
Promoting Civility at Work (helps maintain team harmony during holiday crunch time)
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.
For example, we notice many businesses forget to make sure they have the current address of employees recently let go. A case of out of sight, out of mind can have serious legal repercussions if businesses don’t send out a W2 to ex-employees from that year. Admin tasks aren’t the most exciting thing during the season, but they’re important.
Here’s a 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. We also heavily advise against the use of AI for creating employee handbooks catering your business’s industry and specific legal requirements in your state/region. Mishandling a legal issue at work and relying on AI can worsen the problem and put your business at risk.
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:
Open Enrollment 2025: The Retention Power of Smarter Benefits
Understanding Level-Funded, Self-Funded & Traditional Health Plans
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.
5. Move From Year-End Cleanup to Strategic Workforce Planning
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. Run a Strategic Workforce Planning Audit Before the New Year
Phase 1: Strategic Alignment (Are Your People Aligned With Revenue?)
Before approving a single new hire for 2026, leaders should ensure their talent strategy mirrors their business strategy — not just last year’s headcount.
Talent-to-Value Mapping
Look at your 2026 revenue goals and identify the specific roles (not just departments) that will disproportionately drive results. Do you have your strongest performers in those critical seats?
Build vs. Buy Decisions
For new initiatives like AI integration, automation, or market expansion, decide now whether you will:
Build by upskilling your current team (6–12 months), or
Buy by hiring externally (3–6 months).
Waiting until Q1 often puts companies behind competitors.
Org Chart Stress Test
Review your organizational structure:
Are there too many layers?
Are managers stretched too thin?
Is decision-making bottlenecked?
December is the best time to simplify before new goals roll out.
Phase 2: Retention & Succession Risk (Protect Your Top Talent Before January)
Many employees wait for year-end bonuses before making career moves. January is historically one of the highest voluntary turnover months.
Flight Risk Assessment
Identify your top 10% of performers and ask:
Who is most likely to be recruited externally in Q1?
Who has disengaged quietly?
Proactively speaking with these employees now can prevent surprise resignations later.
Single Point of Failure Check
If only one person knows how to perform a critical process, your business is exposed. Cross-train or document before year-end.
Succession Planning Reality Check
If a key leader were to leave unexpectedly, is there a clear internal successor? If not, that gap becomes a 2026 priority.
Phase 3: Capacity & Cost Planning (Stop Treating Headcount Like Simple Math)
Rather than rolling over last year’s headcount, December is the time to zero-base workforce planning.
“Ghost Work” Audit
Identify tasks that no longer support company goals but still consume hours. Eliminating low-value work can free capacity without hiring.
Scenario Planning
Prepare two workforce plans:
A growth scenario if revenue increases
A downside scenario if targets are missed
This prevents emotional, reactive hiring decisions in Q1.
Contractor vs. FTE Balance
In uncertain markets, increasing variable labor (such as contractors or fractional support) gives businesses flexibility without long-term salary risk.
Phase 4: Culture, Compensation & Burnout Prevention
Market Compensation Check
Compensation data shifts quickly. If your salary bands aren’t adjusted for current market conditions, retention risk rises.
Burnout Thermometer
If your highest performers aren’t using PTO, that’s a red flag — not a badge of honor. Burned-out leaders struggle to execute Q1 plans effectively.
RTO & Hybrid Policy Consistency
If different teams are being held to different standards, resentment builds quickly. December is the right time to reset expectations for 2026.
The Most Important Action Item Before Year-End
If leaders only take one step from this entire process, it should be this:
Conduct stay conversations with your top three performers before the holidays.
Ask each one:
“What would make you leave next year?”
“What would make you stay?”
Their answers will quietly define your 2026 retention strategy.
7. 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 becomes more than a cleanup sprint — it becomes the foundation for a stronger 2026. When compliance, culture, capacity, and talent strategy are aligned before the new year begins, teams enter Q1 focused instead of reactive.
Not Sure How Strong Your People Strategy Is?
In less than two minutes, our People Strategy Readiness Check can highlight risks, gaps, and growth opportunities before 2026 begins.
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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.
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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.
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Yes. Market conditions, labor costs, technology, and employee expectations evolve quickly. Businesses that revisit their workforce strategy annually are better positioned to retain talent, manage costs, and scale with fewer disruptions.
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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.
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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.
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January is historically one of the highest voluntary turnover months because many employees wait to receive year-end bonuses before resigning. If businesses don’t proactively assess engagement, compensation competitiveness, and workload balance in December, they risk losing top performers right as Q1 execution begins.
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Stay conversations are proactive one-on-one meetings with high-performing employees focused on what keeps them engaged and what might cause them to leave. Conducting these before year-end helps leaders address retention risks early, rather than reacting to surprise resignations in January.
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Instead of rolling over last year’s headcount, businesses should evaluate which roles directly drive revenue, where capacity is being wasted, and how contractor vs. full-time labor should be balanced. December is the best time to align hiring plans with operational priorities before budget approvals lock decisions in.
