Open Enrollment Enrollment Checklist and Tips

Post it notes stuck to a bulletin board with ideas for open enrollment.

Open enrollment is only a few weeks long. But it can often feel like it lasts most of the year! We’ve put together a checklist and strategy for you to make the most out of open enrollment.

[ ] Plan Ahead

Give yourself at least 2 months of lead-time before open enrollment begins to get ready. If you have more time, even better.

As open enrollment draws closer, schedule time to meet with your team. Review last year’s open enrollment retrospective to see what went well and what didn’t.

Similarly, take time to look at last year’s open enrollment calendar. See if you had enough time to effectively manage open enrollment.

[ ] Start Building Plans

If you start early enough, you can have more in-depth conversations with your benefits providers. Ask what’s new this year and what benefits you can offer to employees.

Use this time to also start building out a rollout plan. Create summaries, gather plan documentation, evaluate costs, and take screenshots of web portals.

[ ] Start Communicating

Finally, start communicating with your employees about open enrollment.

Even if plans haven’t changed, employees’ situations may have. Take the time to communicate as many aspects of this year’s plans as you can to your employees.

Even if it feels redundant, over-communicate the process of enrolling.

[ ] Schedule Follow-Ups

Before you open up the benefits signup portals to employees, reserve time on your calendar throughout open enrollment to answer employee questions about enrollment or changes to their plans.

As you’re communicating with your employees about open enrollment season, let them know you’ll be available for Q&A sessions.

In our engagement guide, we recommend creating videos that answer common enrollment questions and posting the video library in an easy to find location so that employees can use the resource as they’re navigating the enrollment process.

[ ] Ensure Everything is Working

Before you officially open your benefits portals to employees, do a test run (or three) to check if everything is working properly and that rollout is smooth.

Work with your benefits providers to create test accounts to see how emails, communication tools, and benefits information is presented to employees. Your providers likely have test accounts they can share with you to let you explore benefits portals and simulate the employee experience.

You can also use this opportunity to create video of the registration and benefits enrollment process. Add them to your FAQs portal to help employees down the road.

Depending on the size of your organization, you may need to create videos to streamline the process of assisting employees with their signups.

[ ] Think About Communication Methods

Not every employee wants to receive flyers or handbooks explaining new benefits processes. Adapt your communication and rollout strategies to fit with your organization’s personas and employee profiles.

To figure out what communication methods work most effectively, build employee benefits personas to see how your employees prefer to communicate.

[ ] Make Communication Efficient

Although we emphasized over-communicating how benefits work with your employees, don’t feel like you need to write a novel every time you send an email. Keep communication efficient and concise so that employees don’t get burned out.

Instead of sending out carbon copies of your plan documentation, give just the highlights and direct employees to deeper resources if they want more information.

Have you started thinking about your next open enrollment period yet? We hope this open enrollment checklist has been helpful.


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