Open Enrollment Starts Soon: How to Prepare Employees (and Yourself)

For HR teams, open enrollment season often brings a mix of urgency, repetition, and stress. But with preparation and thoughtful communication, it doesn’t have to be a scramble. In fact, it’s one of the best opportunities all year to build trust, demonstrate value, and empower employees to make smart choices about their benefits. Here’s how to get ahead of the curve and make open enrollment smoother and more successful for everyone.

Start Sooner Than You Think
One of the biggest mistakes is waiting too long to start. Begin your outreach at least four to six weeks before enrollment opens. This gives employees time to digest information, ask questions, and discuss options with family. It also creates breathing room for your team to troubleshoot issues before they become urgent.

Communicate Clearly and Often
Benefits can be complex—and overwhelming. Use plain language, break content into bite-sized pieces, and repeat key messages through multiple channels: email, intranet posts, posters, and manager announcements. Consider video explainers or interactive PDFs to bring clarity to plan changes and deadlines.

Equip Your Managers
Your people managers are key messengers. Give them the tools they need to reinforce open enrollment updates in team meetings or 1:1s. A quick manager guide with talking points, deadlines, and escalation paths can go a long way toward extending your reach.

Create Accessible Support Channels
Offer multiple ways for employees to get questions answered—live webinars, on-demand FAQs, office hours, or quick Slack AMA (Ask Me Anything) sessions. Make sure your resources are mobile-friendly, especially for deskless or hybrid workers.

Promote the "Why"
Don’t just focus on logistics. Remind employees why this matters. Connect benefit decisions to health, financial well-being, and peace of mind. Highlight real-life scenarios to show how benefits impact them and their families.

Conclusion
Open enrollment doesn’t have to feel like chaos. With the right lead time, communication strategy, and manager support, HR can turn this moment into a meaningful, empowering experience for employees—and a more manageable process for your team.