Open enrollment checklist: 5 crucial questions for HR teams

August 25, 2026

For many companies, this time of year marks the start of a busy benefits enrollment season, with HR teams focused on coordinating communications, deadlines and employee elections. But once enrollment closes, a more important question remains: did employees make informed decisions and understand the value of the benefits available to them?

Enrollment success isn't measured by participation rates alone. Most organizations will know their participation rates within days of enrollment closing. The real test is whether employees understand the value of the offerings, make informed decisions that meet their needs and feel confident using those benefits throughout the year. According to recent research, employees who understand their benefits extremely well are far more likely to be satisfied with them, yet only 15% of workers say they fully understand what options are available, how they work and how to access them.¹

Open enrollment provides a critical opportunity to educate employees about plan options, in turn fueling employee satisfaction. It can serve as a launch point for clear communication, greater benefits awareness and a better employee experience long after elections are submitted.

Is your HR team ready? These five questions, paired with our open enrollment checklist, provide actionable insights and tools to help make this an effective enrollment season.

1. Are employees equipped to choose the benefits that meet their needs?

Enrollment materials often contain a significant amount of benefits information, but more information doesn't always lead to better decisions. It's the quality of those communications that matters most. Employees who say their employers communicate benefits "very" or "extremely" well are significantly more likely to understand the benefits available to them.²

As you design messaging around benefits education, focus on helping workers understand what has changed, how different options compare and the decision-making tools available to them. It's also important to consider your audience and which benefits may be most relevant to them, as employees at different life stages have diverse needs.

"The most effective enrollment strategies don't focus solely on benefits, they focus on employees," according to Kevin McCrarey, Associate Vice President of Enrollment Strategy at Unum Group. "The workforce brings different needs, questions and life experiences into enrollment. Communications should reflect that reality."

Pressure-test your messaging. Before open enrollment begins, review all messaging from an employee's perspective to ensure they're being given the insight they need to make informed choices:

Confirm that plan changes are clearly explained.
Ensure decision-support tools, including informational videos, flyers and worksheets, are readily available.
Schedule communications to be delivered through multiple channels, including benefits websites, intranets, emails and enrollment materials.

2. Can employees see the full value of their benefits package?

Employees don't experience benefits in silos. And life events rarely require just one benefit. A medical condition may involve health insurance, disability coverage, paid leave and employee support resources. A new child may require leave benefits, caregiver support and financial planning tools.

Accordingly, enrollment communications should focus on how medical, disability, leave, wellbeing and support resources work together to meet workers' changing needs.

This is important because benefits continue to play a critical role in attracting and retaining talent. More than half of employers say voluntary benefits help differentiate their organization when competing for talent,³ and two-thirds of employees say their benefits package makes them more likely to stay with their employer.²

Connect the dots for employees. When employees understand the full ecosystem of support available to them, they are better positioned to recognize the value of their benefits package. Help workers understand how benefits support real-life moments:

Show how medical, disability and leave benefits work alongside voluntary benefits like accident, critical illness, hospital and life insurance.
Frame benefits around life events rather than product categories.
Highlight resources employees may need before, during and after major life changes.

3. Are your managers and HR team ready for benefits questions?

Even the strongest enrollment experience won't eliminate employee questions. In fact, responding to employee questions is still the most time-consuming HR activity associated with benefits administration.³

With 70% of workers reporting they prefer having at least one benefits communication channel that allows them to speak with a person,² it’s important to equip managers with the information they need to provide their teams with direct, accurate support about available options and how they work together. Employers can also strengthen benefits understanding by connecting employees with the expertise of their carrier and broker partners. This collaborative approach provides personalized support, improves confidence in benefits decisions and helps alleviate administrative pressures on HR teams.

Prepare your people and make help easy to find. Consistent messaging and accessible support can reduce confusion while helping employees feel more confident throughout the enrollment process. As you proactively prepare for workers' potential questions:

Make benefits experts available to employees throughout the year. This is a service your carrier and broker should provide.
Survey employees (both before and after enrollment) to determine their level of understanding around benefits and the enrollment experience.
Clearly communicate where employees should go for help.

4. Is the digital experience complemented with personalized support?

The enrollment experience has become increasingly virtual, with digital tools, automation and AI agents helping to simplify the education and election process. This reflects employees’ preferences for online enrollment.²

These tools should be used to enable enrollment, but many employees continue to express a desire for human interaction, so it’s ideal to have both options available to employees.

"Technology can simplify decisions and human support can build confidence," says McCrarey. "When you have the technology, the decision-support tools and the human touch working together, that's when you've hit the sweet spot."

Make confidence easy to access. Employees should be able to navigate enrollment independently when they choose, while still having access to trusted guidance when they need it. Balancing technology and personal support is an effective way to cover all the bases as you head into enrollment season:

Provide intuitive digital enrollment education tools like online guides and landing pages that are designed for different learning styles.
Offer access to knowledgeable experts and clearly communicate how to get in touch with them when questions arise.
Create multiple pathways for employees to get help.

5. What happens after enrollment ends?

For many organizations, benefits communication spikes during open enrollment and then drops off until the following year. But that's often not what employees want or need.

There's a clear disconnect between how frequently workers prefer to receive benefits information and how often many organizations deliver it. While 45% of employees say their employer communicates about benefits only during open enrollment, 73% would prefer to receive benefits information throughout the year.²

That gap matters because enrollment is only one moment in the employee benefits journey. Workers make elections during open enrollment, but they experience the value of those benefits when life events occur throughout the year. Whether they're welcoming a child, managing a health condition, taking leave or caring for a loved one, employees need timely reminders, education and support long after enrollment season ends.

"The goal isn't just getting employees enrolled; it's helping employees understand and use the benefits available to them," says McCrarey. "Don't let the value of those benefits disappear when open enrollment ends."

As you prepare for enrollment, define success beyond participation rates alone. Consider measuring benefits understanding, employee confidence, awareness of available resources and long-term utilization. These indicators can provide a more complete view of whether your communications are helping employees make informed decisions and get value from their benefits.

Extend the conversation beyond enrollment. The most effective enrollment strategies lay the foundation for year-round benefits education, helping employees understand and use their benefits long after enrollment season ends. View open enrollment as the beginning of your benefits communication strategy, not the end:

Identify what metrics to track before enrollment begins.
Build a year-round benefits communication calendar.
Reinforce key benefits through life-event and seasonal communications.

Redefining the measure of enrollment success

When the workforce understands their benefits, everyone benefits; employees are better equipped to navigate life's challenges, HR teams spend less time answering common questions and organizations get more value from the investments they make in their workforce.

Open enrollment may last a few weeks, but the decisions employees make can affect the rest of their year. The most successful organizations don't stop communicating when enrollment closes. They use enrollment as the launch point for an engaging benefits experience that helps employees make informed decisions, access support when they need it and see the value of their benefits long after elections are submitted.

1 LIMRA Benefits and Employee Attitude Tracker, 2025.
2 LIMRA Benefits and Employee Attitude Tracker, 2026.
3 Unum Q2 2026 Employer Insights Pulse Survey
4 LIMRA Benefits and Employee Attitude Tracker, 2024.

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