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Open enrollment planning: where to start when preparing your campaign

To prep you for open enrollment, we’re sharing our favorite tips. First, it’s all about setting up your strategy for success:


You’re already thinking about Open Enrollment. (Let’s be honest, when are you not thinking about OE?) This is your moment. Your Super Bowl. But we know all too well how easy it is to get overwhelmed.

Simple steps can help you and your team—and we’re here to help. To prep you for the big show, we’ll send tips and tricks to your inbox every week.

First, it’s all about setting up your strategy for success:

1. Review Last Year

With your team, spend time recalling learnings from your last OE. Dust off your notes and ask other HR team members to round out your memory. Ask yourselves:

  • What took up more time than you expected during OE?
  • What 2 things could you have done during last year’s OE that would have made this year easier or more successful?
  • When you communicated with your employees throughout the year (outside of OE), what messages or events resonated?
  • What’s the 1 message you wish your executive team knew about your benefits strategy and offerings?
  • What feedback did your health plan partner provide to inform future planning?
  • What data did you get on last year that could inform this year?

2. Ask Your People

Gather intel from your OE participants, in a Google or AirTable form or in quick chats. Keep it to ~5 questions, and ask them:

  • What OE materials do you remember from last year—whether it was something you received, or saw a friend or partner receive?
  • What process do you and your family follow when picking benefits?
  • Were you satisfied with the health plan decisions you made last year?
  • What 2 things would you have wanted to know or do differently, if you had the chance?
  • What are your top 3 questions or concerns about next year’s benefits?

3. Identify Your Challenges

Before you set goals, identify what could derail your plans. Consider whether any of these apply:

  • Are you rolling out big changes for next year’s benefits?
  • Do you have harder-to-reach populations, like remote employees, those with lower access to email, etc.?
  • Do you need to provide materials in multiple languages?
  • What has your company or your employee base struggled with in the past? (Your surveys can help with this answer.)
  • What resources do you have at your disposal? What might be lacking?

Tell us: Is this checklist missing anything? Add your comments below


Your employee experience matters all year long, not just during Open Enrollment.

See how leading companies are doing it differently, in a new Harvard Business Review Analytic Services report.

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