Creating an HR Calendar for the Year: Key Dates and Deadlines

Running a small business or start-up means wearing a lot of hats, and HR often ends up being one of the trickiest to manage. Missing an important HR deadline—whether it’s a compliance update or an employee review—can quickly snowball into bigger problems. That’s why having a clear, organized HR calendar is so important. It keeps you ahead of the game, reduces stress, and ensures your team and company remain compliant and focused.

Why an HR Calendar is Non-Negotiable

Think of your HR calendar as the backbone of your people strategy. A great calendar helps you avoid last-minute scrambles by planning for critical compliance and tax deadlines, keep your team engaged by staying on top of reviews, benefits, and celebrations, and foster trust and confidence in your leadership by demonstrating organization and foresight.

And let’s be honest, there’s enough going on in a small business that you don’t need any surprises. A strong HR calendar is like your insurance policy against chaos.

Key Dates to Include in Your HR Calendar

Compliance Deadlines You Can’t Miss

Every year comes with its own compliance updates, and falling behind can lead to penalties or legal trouble.

• January 31: W-2s and 1099s must be distributed to employees and contractors.
• Mid-February: File Form 941 (Employer’s Quarterly Federal Tax Return) for the fourth quarter of the previous year.
• March 31: ACA filings are due electronically to the IRS.
• October 1: Prepare and distribute Medicare Part D notices before the start of open enrollment.
• End of the Year: Review labor law posters to ensure they are updated for the new year.

Benefits Management Milestones

Managing employee benefits doesn’t stop after open enrollment. The timeline below can be adjusted based on the company’s open enrollment date.?

• November: Open enrollment communication begins to ensure employees are informed about their options.
• December 1: Confirm benefits changes with vendors for the next plan year.
• Mid-Year (June or July): Conduct a benefits audit to assess employee usage and identify gaps.

Employee Reviews and Development

Don’t let performance management be an afterthought.

• Early January: Annual goal-setting meetings to align individual and team objectives for the year.
• March, June, September, December: Schedule quarterly performance reviews or check-ins to provide feedback and track progress.
• Late October: Begin year-end reviews to identify achievements and areas for growth.

Payroll and PTO Schedules

Payroll errors and mismanaged PTO requests can lead to frustration—and worse, legal headaches.

• Mid-December: Finalize PTO policies and blackout dates for the upcoming year and communicate to employees.
• Payroll Submission Deadlines: Set dates in accordance with your pay cycle and ensure they align with tax deadlines.

Employee Engagement and Culture Building

Your HR calendar can also be a tool to strengthen your culture. Here are some examples.

• February: Plan for Black History Month celebrations.
• May: Recognize Mental Health Awareness Month with activities or resources.
• October: Host team-building events or retreats to re-energize employees before the busy holiday season.
• November 15: Plan an Employee Appreciation Day ahead of Thanksgiving to show gratitude.

Tips for Building an HR Calendar That Works

• Be realistic: Start with the must-dos (compliance deadlines) and layer in the nice-to-haves (culture-building activities).?
• Involve your team: Ask managers or team leads for input to ensure nothing important slips through the cracks.?
• Leverage tools: Use calendar apps, HR software, or even a shared spreadsheet to keep everyone on the same page.?
• Review and adjust quarterly: Things change, whether it’s new legislation or evolving team priorities. Schedule time to revisit and tweak the calendar.

How CultivaHR Can Make a Difference

At CultivaHR, we specialize in helping small businesses and start-ups streamline HR processes and stay ahead of deadlines, so you can focus on what you do best.

Need help creating an HR calendar tailored to your business? Or maybe you’re not even sure where to start? Let us take the guesswork out of it. From compliance updates to employee engagement strategies, we’ve got you covered.

Contact CultivaHR today to start building a better HR foundation for your business. Let’s make this your most organized and impactful year yet!