Navigating Open Enrollment with Confidence: How Employers Can Support Smarter Benefit Decisions

Open enrollment season is one of the most important -- and overwhelming -- times of year for employees. Faced with a maze of plan options, changing policies, and unfamiliar terms, many employees end up making rushed or uninformed choices that don't align with their needs. (In fact, a 2024 Voya study found 47% of benefits-eligible employees say reviewing voluntary benefit options is difficult, highlighting how easily employees can miss key offerings.)

For HR teams, there's a bigger picture: Open enrollment is about maximizing the ROI of your total rewards strategy and improving workforce well-being. When employees choose plans that don't meet their needs (or avoid engaging altogether), it leads to underutilized benefits, greater financial stress, and missed opportunities for impact.

That's why open enrollment is such a critical moment. With the right communication, tools, and support, HR leaders can empower employees to make confident, informed choices and help them connect those choices to their broader financial and personal well-being.

The Challenges of Open Enrollment

Open enrollment is a pivotal moment for employees to engage with their benefits, but it's also one of the most complex and high-pressure periods of the year. When employees are overwhelmed or under-informed, it can lead to poor plan selections, missed benefits, and increased financial stress that lingers far beyond the enrollment window.

These challenges don't just affect employees -- they create ripple effects across HR teams, as well. When enrollment goes poorly, HR faces a higher volume of questions, more administrative corrections, and lower ROI on benefits programs overall. Understanding these barriers is the first step toward improving the experience and the outcomes for everyone involved.

Here's how common open enrollment challenges impact both employees and employers:

Lack of Context

Employees don't always understand how each benefit option connects to their personal financial goals or life circumstances. For instance, a new parent might not realize how a Dependent Care FSA could help reduce childcare expenses -- or may miss enrollment entirely because they didn't see how it applied to their current needs. Similarly, an employee managing a tight budget with little room for unexpected costs might benefit from HSA contributions or cost-sharing strategies, but without clear guidance on how those benefits can ease their financial strain, they may choose a plan that doesn't meet their needs.

Last-minute Decisions

With limited time and competing priorities, many employees wait until the last minute to choose their plans. This can lead to hasty decisions or defaulting to last year's elections, even if their situation has changed significantly.

Rushed decisions often result in misaligned coverage, overlooked benefits, and missed opportunities to save money or build financial security. For HR teams, this can translate into higher administrative burden, lower benefits utilization, and increased questions or corrections after enrollment closes -- all of which diminish the overall ROI of the organization's benefits strategy.

Fear of Getting It Wrong

When faced with too many options or unclear information, employees can experience decision paralysis. Instead of confidently selecting the plan that best fits their needs, they may delay making benefits elections, unsure of what to do and afraid of making the wrong choice. As a result, many default to the status quo or select the cheapest option without fully understanding the trade-offs, which can lead to higher out-of-pocket costs or insufficient coverage down the line.

When employees make choices out of fear or confusion, they're less likely to select plans that align with their real needs. For employers, this can result in low satisfaction with benefits, increased financial stress, and a weaker overall perception of the organization's total rewards offering.

All of these challenges can result in missed opportunities, underutilized benefits, and long-term confusion about what employees actually signed up for. Supporting employees with clear, relevant, and timely information can turn this high-stakes decision into a calm, confident, and informed choice.

Why Employee Confidence Matters During Open Enrollment

When employees understand their benefits, they feel far more confident in their decisions. In a 2024 HealthEquity survey, employees who reported excellent understanding of their benefit choices were four times more likely to feel confident in their selections compared to those with poorer understanding.

Employees who feel confident navigating open enrollment are more likely to:

• Select plans that truly meet their health, financial, and personal needs
• Understand how to maximize employer-sponsored benefits like HSAs, FSAs, and 401(k) matches
• Feel supported and valued by their organization
• Engage with other wellness resources offered year-round

When faced with too many options or unclear information, employees can experience decision paralysis. Instead of confidently selecting the plan that best fits their needs, they may freeze -- unsure of what to do and afraid of making the wrong choice. As a result, many default to last year's selections or choose the lowest-premium option without realizing it might cost them more later.

Regardless of income or financial experience, every employee deserves the opportunity to make informed decisions about their benefits. When that confidence is missing, it can lead to missed savings, underused resources, and avoidable financial strain, all of which affect not only personal well-being but also workplace satisfaction and benefit ROI.

5 Ways Employers Can Boost Confidence During Open Enrollment

1. Start Early & Communicate Often

Give employees plenty of time to explore their options. Launch your open enrollment communications at least 4-6 weeks in advance and continue through the deadline. Use multiple channels (email, Slack, meetings) to reach employees where they are.

Early communication especially helps employees who need more time to process options, ask questions, and seek guidance before making decisions.

2. Make Benefits Information Digestible

Break down plan summaries into simple, human language. Use comparison charts, short videos, FAQs, and decision-support tools to help employees quickly understand key differences and trade-offs. Avoid jargon whenever possible.

This approach is crucial for employees who may not have the financial background or time to decode complicated terminology. Clear, straightforward materials help them make more confident decisions.

3. Connect Benefits to Real-Life Scenarios

Help employees see how each benefit supports their financial and personal goals. When benefits information feels relevant and timely, employees are more likely to engage, ask questions, and make confident choices.

For instance, you might:

• Explain how a Health Savings Account (HSA) can help a mid-career employee save on taxes while preparing for future medical expenses.
• Highlight how a Dependent Care FSA can support a working parent navigating the high cost of childcare.
• Show how supplemental insurance might provide peace of mind for a newly independent employee who hasn't built up an emergency fund yet.

4. Offer Personalized Guidance

Pair open enrollment with financial wellness tools or coaching. Employees are more confident when they have access to:

• One-on-one sessions with financial planners
• AI-driven guidance based on their life stage and goals
• Budgeting tools that show how benefits fit into their overall financial picture

A newly hired, young professional employee might benefit from basic budgeting and understanding how to prioritize benefits, while someone nearing retirement may need help optimizing their investment strategy or planning withdrawals. Personalized tools and coaching ensure every employee, regardless of where they are in their personal or professional journey, feels supported and equipped to make the right decisions for their future.

5. Follow Up with Post-Enrollment Support

Once enrollment closes, don't go silent. Keep the conversation going with timely reminders about how and when to use benefits, guidance on common questions (like how to file an HSA reimbursement or access mental health services), and updates that help employees make the most of their choices year-round. Encourage employees to revisit their elections if they experience a major life event such getting married, having a child, or changing jobs.

For HR teams, this ongoing support reduces confusion, limits avoidable errors, and cuts down on time spent answering repetitive questions. It also drives better engagement and utilization across your benefit offerings, maximizing your investment and helping employees see your total rewards strategy as a valuable part of their overall compensation.

Conclusion

Open enrollment doesn't have to be a source of stress for employees or HR teams. With the right strategy, communication, and support, you can turn it into a moment of empowerment.

By helping employees understand their options and feel confident in their choices, you're not just managing a process. You're building financial wellness, trust, and long-term engagement across your workforce. For HR leaders, that translates to fewer last-minute questions, higher-benefits utilization, and a better return on your total rewards investment. When employees make informed decisions, everyone wins.

Additional Resources

Set yourself up for success during Open Enrollment by exploring BrightPlan's Key Strategies for Open Enrollment Success. This includes an Open Enrollment Checklist, a helpful eBook guide to keeping the employee experience at the front of your organization's Open Enrollment period, and more.