WHY THIS MATTERS
Open Enrollment takes months of planning and execution. But when it’s over, most teams just move on. No pause. No debrief. No documentation of what went wrong (or right).
This is the biggest pitfall of all. Because it means instead of flagging and learning from mistakes, teams repeat them the next year. And is OE ever really over? Not really. It’s an ongoing process throughout the year.
WHAT GOES WRONG
- Benefits administration issues resurface year after year
- Teams forget prior challenges and can’t mitigate risks for next OE
- Checklists stay static, instead of evolving as living documents
- Valuable lessons are lost as people change roles.
ROOT CAUSE
- No clear ownership for OE success or documentation
- Lack of structure for capturing lessons learned
- No scheduled debrief with HR, Payroll, VENDOR, and BROKER teams
- Limited experience to know what to track or improve
HOW TO FIX IT
- Hold a post-OE debrief with all stakeholders
- Document lessons learned and update OE checklists
- Assign owners for each improvement so fixes don’t get lost
- Treat OE as a cycle of continuous improvement, not a one-time event
- Tie OE process success to long-term workforce and business goals (risk mitigation, compliance, cost control, employee experience etc.)
✦ INSIDER INSIGHT
The most successful benefits teams I’ve worked alongside always close OE with a debrief. A few hours invested now saves weeks of headaches the following year.
Want to avoid costly surprises during Open Enrollment? We can help. Let’s connect.


