Open Enrollment may still be months away, but the most successful enrollment seasons begin with early, thoughtful planning. Strategic preparation helps HR teams avoid last-minute scrambles, ensures compliance, and improves employee engagement and satisfaction with benefit offerings. Whether this is your first time managing Open Enrollment or you’re looking to refine your process, starting with a strong foundation makes all the difference.
Strategic planning for Open Enrollment should begin several months in advance. Many HR teams start laying the groundwork in June or July, especially if their enrollment period occurs in the fall. Early planning gives you time to review your current offerings, gather feedback, work with vendors, and develop communication timelines.
Think of this stage as a discovery phase: reviewing what worked last year, identifying gaps, and exploring opportunities to improve.
A critical element of strategic planning is assessing how well your current benefits are serving your workforce. Rather than defaulting to the same offerings year after year, take time to analyze how your programs are performing, both in terms of employee satisfaction and cost-effectiveness.
Start by reviewing these key data points:
Examine which benefits employees actually used, and how frequently. Are certain health plans underutilized? Did your EAP or wellness programs see engagement? Utilization data helps identify both high-value offerings and potential redundancies.
Survey employees to understand their experience with the benefits enrollment process, plan options, and perceived value of offerings. Qualitative feedback can uncover pain points or confusion that raw data alone might miss.
Review your benefits providers to ensure they’re meeting service expectations. Are customer service issues driving employee dissatisfaction? Are costs rising faster than expected without a corresponding increase in value? Now is the time to consider renegotiating contracts or exploring alternative vendors if needed.
Look at broader patterns in your workforce. Is there growing demand for mental health support? Are family-building or caregiving benefits relevant for your demographic? Identifying emerging needs helps you stay competitive and relevant as an employer.
Together, these insights guide strategic decisions on what benefits to retain, improve, or phase out.
If you haven’t already implemented a post-enrollment survey, consider making it a priority this year. Surveys give employees a voice in shaping future offerings, and the feedback can uncover valuable information about communication gaps, misunderstood policies, or underutilized benefits. Use that input to refine both your benefit design and your communication approach for a more effective, employee-centered Open Enrollment season.
After evaluating the performance of your current benefits, the next step is to establish a financial foundation for the year ahead. This process requires collaboration between HR, finance, and company leadership to ensure your benefits strategy aligns with organizational goals and budget realities. Begin the process by reviewing key financial considerations.
Work with your benefits broker or provider to understand expected premium changes. Many plans experience annual increases, particularly in areas like medical, prescription, and mental health coverage. Identifying these changes early gives you time to explore alternative plan designs or cost-containment strategies.
Revisit how costs are currently split between the organization and employees. Is your contribution strategy competitive with industry standards? Are employees bearing a growing share of the cost year over year? Strategic adjustments here can support recruitment, retention, and employee satisfaction, especially if rising costs are offset by enhanced offerings or support.
If you're considering adding new benefits, such as mental health resources, fertility assistance, or wellness stipends, include their projected costs in your planning. Determine whether these will be employer-funded, employee-paid, or offered as voluntary add-ons. Balance innovation with sustainability to ensure new offerings are impactful and manageable.
Explore opportunities to optimize your current benefits through plan redesign, bundled services, or vendor consolidation. You may find cost savings in adjusting plan tiers, adopting high-deductible options with HSA contributions, or switching to vendors with stronger performance or pricing.
Proactively addressing these financial elements early in the planning process sets the stage for more transparent, confident communication with employees. When you're clear on where changes are coming from and why, you can craft messaging that builds understanding and trust, especially if employees are affected by increased costs or plan changes.
This stage also offers an opportunity to align benefits philosophy with company values. Whether your goal is to increase equity, support wellness, or enhance family care options, your budgeting decisions shape not just what you offer, but how employees perceive their value within the organization.
While much of Open Enrollment planning focuses on plan design and employee engagement, it’s also a key moment to revisit compliance. With benefits plans governed by a range of federal and state laws, ensuring regulatory accuracy is essential to avoid penalties, maintain employee trust, and support organizational integrity. Use this time to conduct a thorough compliance review.
Affordable Care Act (ACA) Requirements
Confirm that your health plans meet the ACA’s affordability and minimum essential coverage standards. Double-check eligibility tracking for full-time employees and ensure your reporting processes (such as Forms 1095-C and 1094-C) are ready for timely submission. This is also a good time to verify that variable-hour employees are being measured appropriately if applicable.
Ensure your Summary Plan Descriptions (SPDs), Summary of Benefits and Coverage (SBC), and other required ERISA documents are up to date and distributed properly. If you are undergoing plan changes or vendor transitions, review your COBRA administration procedures to ensure qualified beneficiaries receive timely and compliant notices.
Review how employee health information is handled, especially if using new platforms or vendors. Ensure Business Associate Agreements (BAAs) are in place and that your internal teams understand the importance of safeguarding protected health information (PHI) in accordance with HIPAA regulations.
Depending on your organization’s geographic footprint, you may need to comply with additional state-mandated requirements. These could include specific health coverage mandates, paid leave laws, or notice requirements related to mental health parity or fertility benefits. If your company operates in multiple states, confirm that benefit offerings and communication strategies are tailored appropriately.
Regulatory notices should not be an afterthought. Build timelines into your Open Enrollment plan to ensure that documents are updated, accurate, and distributed within the required timeframes. This also applies to plan changes that require a Summary of Material Modifications (SMM) to be sent out.
Key documents to keep in mind are:
● The Notice of Coverage Options under the ACA
● HIPAA privacy practices notices
● CHIPRA (Children’s Health Insurance Program) notices
● Women's Health and Cancer Rights Act (WHCRA) disclosures
● Medicare Part D creditable coverage notices
Compliance messaging doesn’t have to be intimidating. By integrating reminders and educational materials into your Open Enrollment communications, you can empower employees to make informed choices while fulfilling legal obligations. Pair legal notices with clear explanations in plain language, and always provide a point of contact for compliance-related questions.
Ensuring your benefits offerings and documentation meet regulatory standards helps to avoid risks and facilitate a trustworthy employee experience. A proactive compliance strategy keeps your organization protected while reinforcing confidence among your team.
A well-timed communication plan is one of the most effective tools for increasing engagement and reducing confusion during Open Enrollment. Even the most robust benefits package can go underutilized if employees don’t understand what’s available or how to access it. By mapping out key messages and touchpoints ahead of time, HR teams can help employees feel more confident and supported throughout the process.
8–10 Weeks Before Enrollment
Kick off early awareness.
Start by building anticipation. Send a “Coming Soon” message to alert employees of the upcoming Open Enrollment period. This is a good opportunity to share why Open Enrollment is important, when it will occur, and what types of changes may be expected this year.
6 Weeks Before Enrollment
Distribute Total Rewards Statements.
Providing employees with a personalized view of their compensation and benefits helps build context and appreciation. This transparency supports more informed decisions when it's time to select new benefit options.
5–6 Weeks Before Enrollment
Enable managers to support the process.
Equip managers with talking points, FAQs, and high-level information about benefits. As trusted leaders, managers play a key role in reinforcing messages and helping answer employee questions.
3–4 Weeks Before Enrollment
Preview changes and updates.
Communicate detailed plan comparisons, cost changes, and any updates to policies. Promote benefits info sessions and share resources that help employees evaluate their choices.
2 Weeks Before Enrollment
Send clear enrollment instructions.
Make it easy for employees to take action. Include step-by-step guides on how to enroll, platform access instructions, key deadlines, and where to go for support.
During Enrollment Period
Send reminders and quick tips.
Keep benefits top of mind by delivering short reminders and deadline alerts. Use a mix of channels — email, intranet, digital signage, or HR chat tools — to ensure consistent visibility.
1–2 Weeks After Enrollment Closes
Confirm selections and outline next steps.
Send personalized confirmation messages that recap selected benefits. Share what comes next, including when new coverage begins or how to make corrections if needed.
3–4 Weeks After Enrollment
Gather feedback and evaluate.
Conduct a post-enrollment survey to collect feedback from employees. Insights gained here will help improve future enrollment cycles and communication strategies.
Planning ahead and delivering information in digestible, well-timed pieces empowers employees to make informed decisions while reinforcing the value of their benefits. An organized communication strategy is not only a tactical win — it’s a trust-building opportunity that supports long-term engagement.
Today’s employees expect more than a list of benefit options, they expect tools, context, and personalized guidance that help them make the best choices for their unique circumstances. As benefits become more complex and diverse, HR teams must create resources that simplify the decision-making process and answer common questions before they turn into confusion or inaction. Start by offering a range of formats to meet employees where they are.
Comparison Guides for Plan Options
Break down each benefits plan side-by-side, highlighting differences in cost, coverage, and key features. Use real-world examples or scenarios to illustrate how different plans might apply depending on life stage, family size, or health needs.
Interactive Microsites or Enrollment Portals
Centralize all benefits information in one easy-to-navigate space. Interactive tools can help employees explore their options, view eligibility details, access required forms, and connect with support, all from a single hub.
Office Hours or Virtual Q&A Sessions
Schedule informal sessions where employees can ask questions live. These can be hosted by HR team members, benefits brokers, or healthcare providers to address concerns in real time. Offering multiple time slots or recordings ensures accessibility for all teams.
On-Demand Videos or Webinars
Create short explainer videos that walk employees through plan changes, new offerings, or how to enroll. These can be used repeatedly across multiple channels and are especially helpful for visual learners or remote workforces.
Total Rewards Statements
Distribute personalized Total Rewards Statements before Open Enrollment begins to provide a clear picture of what each employee currently receives. This context helps employees better understand the full value of their compensation and benefits, making it easier to evaluate what to keep and what to change.
When these resources are built with clarity, accessibility, and personalization in mind, they empower employees to make informed, confident choices along sith reducing confusion and minimizing follow-up questions for HR. The result is a more engaged workforce and a smoother, more effective Open Enrollment process.
Open Enrollment is more than a time to select benefits, it’s a strategic opportunity to reinforce the full value your organization provides. By aligning Open Enrollment efforts with your broader Total Rewards strategy, HR teams can shift the conversation from transactional choices to a more holistic view of employee value.
Use personalized Total Rewards Statements or summaries to highlight how compensation, employer-paid benefits, health and wellness programs, retirement contributions, and additional perks all come together to support employees' total well-being. This personalized context empowers employees to make informed decisions that reflect their individual needs.
In addition to outlining benefit plan options, use this time to spotlight other key elements of your Total Rewards philosophy, such as:
● Career development programs and training opportunities
● Financial wellness resources and planning tools
● Wellness incentives and mental health support
● Company-paid benefits that employees may overlook
When you integrate these components into your communications, employees gain a clearer understanding of what your organization invests in them, beyond salary or insurance coverage. A unified Total Rewards approach helps reinforce your culture, boosts employee confidence during enrollment, and increases appreciation for the full range of offerings your organization provides.
Strategic planning for Open Enrollment is more than an administrative task, it’s an opportunity to strengthen employee trust, demonstrate the value of your benefits, and align your offerings with organizational goals. By starting early, building a clear communication plan, and incorporating Total Rewards Communication throughout the process, HR teams can turn enrollment season into a meaningful experience that supports engagement, satisfaction, and retention. With the right strategy in place, you’ll not only streamline Open Enrollment but also lay the foundation for a stronger workforce year-round.