Open Enrollment Checklist
Use this checklist to reduce stress, errors, and last-minute fire drills during open enrollment.
Open Enrollment Simplification Checklist (HR & Leadership)
3–6 Months Before Open Enrollment
☐ Review last year’s enrollment issues, errors, and missed deadlines
☐ Analyze employee feedback and common benefit questions
☐ Audit benefit plans and remove redundant or low-usage options☐ Confirm compliance requirements, IRS updates, and carrier deadlines
☐ Set clear goals (fewer questions, fewer errors, higher participation)2–3 Months Before Open Enrollment
☐ Segment employees by life stage (single, families, near retirement)
☐ Create a phased communication plan (teaser → education → reminders)
☐ Write plain-language benefit summaries and comparisons
☐ Prepare FAQs based on prior employee confusion
☐ Test enrollment technology and payroll integrations
4–6 Weeks Before Open Enrollment
☐ Announce enrollment dates and upcoming changes
☐ Share plan comparison tools and cost calculators
☐ Schedule live HR office hours or webinars
☐ Confirm mobile access and single sign-on functionality
☐ Centralize all enrollment materials in one platform
During Open Enrollment
☐ Send regular reminders before deadlines
☐ Monitor enrollment progress daily
☐ Use automated validation to prevent errors
☐ Provide real-time support for employee questions
☐ Track engagement and unanswered FAQs
After Enrollment Closes
☐ Confirm elections with every employee
☐ Share coverage start dates and next steps
☐ Review participation and error rates
☐ Survey employees about the enrollment experience
☐ Document improvements for next year
Open Enrollment FAQs
Open enrollment can be confusing, time-consuming, and stressful for both HR teams and employees. These frequently asked questions explain why open enrollment is so challenging, how employers can simplify the process, and what best practices reduce errors, missed deadlines, and employee frustration. Whether you’re looking to improve employee experience, reduce administrative workload, or automate benefits enrollment, these FAQs provide clear, practical answers to the most common open enrollment challenges faced by growing businesses.
Open enrollment is stressful because employees are asked to make complex financial and healthcare decisions under tight deadlines, often using confusing terminology. Without clear guidance or tools, many employees feel rushed, overwhelmed, or unsure they’re choosing the right coverage.
HR teams manage compliance requirements, carrier coordination, employee questions, payroll integrations, and deadlines—all at once. Manual processes and fragmented systems increase the risk of errors and dramatically increase administrative workload.
No. Simplifying enrollment does not mean limiting meaningful choice. It means presenting options more clearly, reducing redundant plans, and helping employees understand which options best fit their needs.
Ideally, planning should begin three to six months in advance. Early planning gives HR time to audit past issues, communicate changes gradually, and provide employees with enough time to make informed decisions.
Common mistakes include:
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Sharing information too late
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Using confusing or technical language
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Relying on manual paperwork
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Offering too many similar plans
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Not providing decision-support tools
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Skipping post-enrollment feedback
Modern HR and HCM platforms can centralize benefits information, automate data flows, provide real-time validation, and offer interactive tools like cost calculators and plan comparisons. This reduces errors while improving employee confidence and engagement.
Active enrollment can increase engagement, but it should be paired with clear communication, reminders, and default options. If employees fail to act, fallback coverage and opt-out options must be clearly defined to avoid coverage gaps.
Providing clear FAQs, side-by-side plan comparisons, decision-support tools, and live Q&A sessions significantly reduces repetitive questions and support requests.
Benefits enrollment is a key trust moment. When the process feels easy, transparent, and supportive, employees perceive their benefits as more valuable and feel more positively about their employer overall.
Track metrics such as participation rates, error rates, missed deadlines, employee feedback, and support volume. Improvements in these areas signal a smoother, more effective enrollment experience.
Legal Disclaimer: This document is intended for informational purposes only and does not constitute legal information or advice. This information is provided in consultation with federal and state statutes and does not encompass other regulations that may exist, such as local ordinances and does not constitute legal advice.
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