Open Enrollment season is here—and with it, the opportunity to turn insights into action, align your internal teams, and streamline the employee experience. While your benefits strategy may already be taking shape, laying the groundwork now will help you stay organized, aligned, and proactive in the weeks ahead. Work together with your broker to set up a smooth OE foundation with this checklist—organized by focus area—and set yourself up for a smooth Open Enrollment.
1. Data gathering: Know what you’re working with
Before planning ahead, take stock of what happened last year.
Pull last year’s reports:
- Enrollment rates by benefit type and employee group
- Benefit utilization data (are employees using what they chose?)
- Cost per employee and total program costs
- Enrollment timing (early vs. last-minute patterns)
Gather feedback:
- Post-enrollment surveys or pulse feedback
- Help desk tickets or FAQs
- Manager insights from the field
- Exit interview notes referencing benefits
2. Stakeholder check-in: Get aligned internally and externally
Who’s involved this year—and are they ready?
Internal team alignment:
- Clarify roles across HR, comms, finance, and legal
- Identify any gaps in process or resourcing
- Set expectations around timelines and approvals
Vendor status review:
- Confirm renewals and plan changes
- Note any new tools, resources, or features to highlight
- Identify vendors that need more support or oversight
- Decide whether to evaluate new partners
3. Know your workforce: Analyze employee shifts
Today’s workforce looks different than last year—make sure your plan reflects that.
Assess workforce changes:
- Any new departments, roles, or locations?
- Major life events affecting benefit needs?
- Trends in new hire demographics?
Evaluate communication preferences:
- What channels reached employees most effectively?
- Were there underserved segments or visibility gaps?
- What new tools or formats could boost reach?
4. Spot opportunities: Remove friction before it starts
What can you improve before OE comms even begin?
Underused benefit review:
- Which benefits had low enrollment but high value?
- Where did employees report confusion?
- Are there any benefits worth sunsetting or spotlighting?
Cost and operations review:
- Are you spending heavily on low-satisfaction plans?
- Can automation reduce admin burden?
- Are there lower-cost alternatives or new voluntary offerings to consider?
Why foundation work pays off
A strong start means fewer surprises later. Getting clear now on what worked, what didn’t, and what’s changed sets you up for:
- Cleaner communications
- Better employee engagement
- Less scrambling during OE month
- Stronger leadership confidence
You don’t have to do it all this week—but take these foundational steps now, and your future self (and your team) will thank you.
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