Preparing for Open Enrollment Season

Open enrollment is a critical component of your people strategy—and we know it can feel overwhelming.

Between evaluating benefit plans and ensuring every team member understands their options, there’s genuine pressure to get everything right. And when a majority of employees struggle to care, the pressure on HR teams and leaders can quickly compound.

But here’s the thing: with thoughtful preparation and a people-first approach, open enrollment transforms from a stressful obligation into a meaningful opportunity to demonstrate how much the company values its people.

Let’s walk through how to approach open enrollment season with confidence.

Start Earlier Than You Think

What’s the most common challenge we see? Teams waiting too long to get started. We recommend starting your planning at least 60–90 days before your open enrollment period. This enables you to collaborate with your benefits partners, thoughtfully assess your current offerings, and explore what’s possible for the year ahead. When you start early, you create space for better decisions, clearer communication, and genuine choice.

Review Current Plans and Utilization

Taking time to understand how your people experienced their benefits over the past year will provide insight to make educated decisions for the upcoming year. Which offerings resonated with your team? Where did you see high engagement, and where might there be unmet needs or gaps in coverage?

This review is your opportunity to:

• Celebrate what’s working well and identify areas for improvement

• Discover new options that better serve your unique workforce

• Find smart ways to optimize costs without compromising quality

• Ensure your benefits strategy truly reflects your people’s needs and your company’s value

This is where having the right benefits administration software and data insights becomes invaluable for making informed, people-centered decisions.

Stay Current with Compliance Requirements

Open enrollment isn’t just about offering great benefits—it’s about doing so responsibly and in compliance with regulations.

Make sure you’re prepared with:

• Current ACA regulations and affordability requirements

• All required employee notices, including SBCs and COBRA information

• Key deadlines for renewals and necessary filings

• Any state-specific requirements that impact your benefit offerings

If your team has grown or changed this year, take time to understand how those changes might affect your compliance responsibilities.

Craft Clear, Helpful Employee Communications

The way you communicate about benefits can make all the difference in how your people experience open enrollment. Start developing materials early—emails, guides, comparison tools, and timelines—so your people have plenty of time to digest information and ask thoughtful questions.

Focus on:

• Using clear, everyday language that everyone can understand

• Clearly explaining what’s new or different this year

• Providing easy-to-use plan comparison tools

• Creating multiple ways for people to get support and answers

Consider hosting live information sessions where employees can ask questions and get real-time support—these conversations often reveal insights that improve the entire process.

Set Up Systems for Success

Even the best benefits and clearest communication need strong administrative support to create a smooth experience for everyone involved.

Take time now to:

• Ensure your HR systems and enrollment platforms are ready and tested

• Verify employee eligibility and classifications

• Clearly define who’s responsible for what across your team

• Build in buffer time well before final deadlines

Having the right HCM can significantly streamline your administrative workload while ensuring accuracy and compliance throughout the process.

Keep Your People at the Center

At its heart, open enrollment is about supporting the humans who make your organization successful. Benefits are deeply personal, and how you approach this process reflects your company’s commitment to your people’s wellbeing.

Make space to:

• Gather feedback before and after enrollment to continuously improve

• Transparently explain the reasoning behind any changes

• Highlight how your benefits investment demonstrates your commitment to your team

• Provide personalized support whenever possible

When your people feel informed, supported, and valued throughout this process, they’re more likely to make confident decisions and feel genuinely cared for by your organization.

Moving Forward with Confidence

Open enrollment doesn’t have to be a source of stress. With early planning, clear communication, and a genuine focus on your people’s needs, you can create an experience that strengthens trust and demonstrates your organization’s values in action.

Remember, this process is ultimately about the people who choose to build their careers with you. When you approach open enrollment as an opportunity to serve and support your team, everyone benefits.