Open enrollment season is one of the most important—and potentially stressful—times of year for employers and HR teams. From selecting benefit plans to communicating options with employees, there’s a lot riding on getting it right. But with the right preparation, open enrollment doesn’t have to be overwhelming. It can actually be an opportunity to improve employee engagement and showcase your organization’s commitment to supporting your team.
Here’s how to prepare for open enrollment season with confidence and clarity.
1. Start Early (Earlier Than You Think)
The biggest mistake employers make with open enrollment? Waiting too long to get started. Begin preparing at least 60–90 days in advance. This gives you time to meet with your PEO, evaluate your current offerings, explore renewal options, and get ahead of potential plan changes or cost increases. Early action means more choices, better communication, and fewer last-minute surprises.
2. Review Your Current Plans and Utilization
Take a close look at how your team used their benefits over the past year. Are employees taking advantage of your health plan, dental, vision, or supplemental benefits? Are there gaps in coverage or requests that keep popping up?
This is your chance to:
- Evaluate what’s working and what’s not
- Explore new plan options that fit your workforce
- Identify cost-saving opportunities or bundling options
- Align your benefits strategy with employee needs and company goals
This is where a PEO really shines by providing data and recommendations tailored to your team.
3. Understand Upcoming Compliance Requirements
Open enrollment isn’t just about options—it’s about compliance, too.
Make sure you’re up to date on:
- ACA regulations and affordability thresholds
- Required notices, such as SBCs and COBRA information
- Deadlines for plan renewals and filings
- State-specific mandates that may impact your benefit offerings
If you’ve had any changes in employee headcount or classification this year, double-check how that may affect your responsibilities as an employer.
Download our 2025 HR Compliance Calendar here.
4. Draft Your Employee Communications Early
Clear communication can make or break open enrollment season. Start developing your employee-facing materials now, including emails, guides, Q&A documents, and deadlines, so your team has time to review and ask questions.
Make sure to:
- Use plain language, not benefit jargon
- Highlight what’s new or changing
- Offer side-by-side plan comparisons
- Provide multiple channels for support (HR, PEO partner, live sessions)
Consider hosting an information session to walk through options and answer employee questions in real time.
5. Plan for a Smooth Administrative Process
Even with the right plans and communication, open enrollment can create administrative headaches if you don’t have the right systems in place.
Now is the time to:
- Ensure your HRIS or enrollment platform is set up and tested
- Confirm eligibility and classification for all employees
- Assign roles and responsibilities across your HR or admin team
- Set internal deadlines well in advance of final submission dates
Working with a PEO partner can dramatically reduce the time you spend on backend processing—and help you stay audit-ready in the process.
6. Center the Employee Experience
At its core, open enrollment is about supporting your people. Benefits are one of the most personal, impactful parts of the employee experience, and the way you communicate and deliver them sends a message about your company culture.
Take time to:
- Ask for feedback before and after enrollment
- Explain the “why” behind any changes
- Show how your organization is investing in employee well-being
- Offer personalized support wherever possible
An engaged, informed employee is far more likely to choose the right coverage and feel confident in your leadership.
Final Thoughts
Open enrollment season doesn’t have to be stressful. With proactive planning, a clear communication strategy, and the right support, you can make it a seamless process that reflects your company’s values and supports your team’s needs.
Need help preparing your open enrollment plan? At Tilson, we support businesses every step of the way, from plan evaluation and compliance to communication and execution. Let’s make this your smoothest open enrollment season yet. Reach out and get started today!
