Open Enrollment All Year Long

By Published On: September 30, 2025

Anyone who has ever been an employee has felt the pressure of coming up against deadlines to make their benefits choices for the next year. Like many employees, I often put it off until I can’t anymore and then race through the information HR has given to me to guide my decision-making.

I’m not alone. A 2019 study by PlanSource, a benefits platform provider, found that employees spend just 18 minutes on average enrolling in benefits plans. The 2023 Metlife Employee Benefit Trends Survey found that 31% of employees procrastinated when selecting their benefits, and 37% wish they’d had more time to make their choices.

HR employees don’t have the option of waiting until the last minute. Their planning takes much longer than the duration of open enrollment. While HR professionals caught up in this year’s “busy season” are understandably not likely to be thinking about 2026 enrollment, it’s never too soon to start planning after this year’s bustle is over.

After you have collected the last benefits forms and done the work of enrolling employees in their selected plans, take a well-deserved breather and then start thinking about next year. The earlier you plan, the more likely you are to preserve your sanity and give employees a smoother enrollment experience.

Planning Ahead

HR professionals know the significant planning that goes into each open enrollment season, as companies must make informed decisions about balancing what’s most attractive to their employees with what they can afford to offer them. Because companies’ financial results can vary year to year, each new open enrollment season can require new strategies to attract and retain the most valuable employees.

Keep these tips in mind as you look toward next year’s enrollment:

1. Gather feedback when open enrollment is fresh in employees’ minds.

People are always more likely to share their impressions of an event in its immediate aftermath. Asking employees for feedback right after they’ve registered for benefits will get the most honest and candid responses. Getting this feedback shouldn’t be onerous for HR if they prepare employee surveys well ahead of open enrollment season.

It’s a good practice to not make your survey too long or granular. As much as possible, keep the survey to multiple choice with write-in options for employees who want to give more specific feedback. Generate higher participation with a gift card raffle for employees who complete the survey on time.

Employee feedback can provide a great starting point for planning for the year ahead. Armed with the fresh feedback you’ve collected and the data you’ve gotten from the previous year’s enrollment will help eliminate guesswork about what employees most value in their benefits and which benefits they are most likely to use.

Also make sure to ask employees about the experience of enrolling as well. Did you communicate the process clearly? Did employees know where to go for information? Were there any areas of confusion? How responsive did they find HR to their questions?

2. Loop in stakeholders early.

Open enrollment isn’t just the job of HR. There are multiple departments and individuals whose input must be taken into account before benefits planning can begin. Other stakeholders can help amplify your messaging to employees. Touch base with your key stakeholders early and let them know when you need information to allow you enough time to prepare for enrollment season. Among those you should reach out to:

  • Finance departments to set or approve budgets for benefit choices.
  • IT to set up the systems you need to make enrollment run smoothly. Make sure you incorporate adequate time for testing so there’s no surprises when employees begin to select their benefits.
  • Company leadership to help you reinforce your messaging and encourage participation.
  • Department heads and managers to connect with their teams and encourage them to choose carefully among their benefits.

3. Build a clear, comprehensive communications plan.

Many employees say they don’t understand their benefits options. MetLife’s 2024 Employee Benefit Trends Study found that 62% of employees are not completely confident they know about all of their benefits, and 45% said they do not fully understand their benefits package. Half of employees said they would feel more cared for by their employer if they received better communication about the benefits their employers offer before open enrollment.

Having adequate knowledge about their benefits is crucial for employees. In response to MetLife’s 2023 benefits survey, 1 in 6 employees said they regretted the benefits decisions they made the year before.

To prevent that regret, employers—through their HR departments—must ensure they have an effective, comprehensive communications plan to educate and inform their employees about the benefits available to them. A comprehensive communication plan should incorporate:

  • A clear timeline: Develop a timeline for next year that delineates milestones within your preparation phase, the open enrollment window, and post-enrollment tasks. Communicate these timelines to all HR staff and start messaging stakeholders about what to expect that year. Use multiple communication channels and tailor them to your audience and how they prefer to access information (email, Slack, intranet, meetings, etc.).

  • An early start: Start reaching out to employees in January with messaging about open enrollment and tell them how to locate resources to educate themselves about their options for the coming year. No need to overload them with information at this point; just give them a heads up for what to expect during the year. Start communicating with employees in earnest with specific details 4-6 weeks before open enrollment begins.
  • A plan for creating consumer-specific resources: Make sure your communications plan details the specific resources you want to develop or revise for the next year. Your intranet is likely the best “home” for these resources when you are ready to go live with them. Provide both high-level information that employees can quickly look over and more detailed information if they want to dig deeper.

At the minimum, your resources should include a comprehensive benefits guide that includes information about all available options, including health, dental, vision, and life insurance; wellness programs; EAP descriptions; and bonus options, such as pet insurance or education support. Include important details, including coverage limits, deductibles, premiums, copays, and any changes from the previous year.

Particularly handy for employees is a FAQ document that provides high-level answers to your most frequently received questions from previous years. You will save yourself a ton of time if you have materials at the ready when you are repeatedly asked the same questions.

4. Invest in employee engagement.

Your communications plan should focus heavily on engaging as many employees as possible with their benefits selection. Meeting employees where they are is an excellent way to address their specific concerns and make sure their choices align with their best interests. A few strategies:

  • Host a vendor fair: Share the responsibilities of educating employees about their insurance options by inviting benefits providers to directly provide that information themselves. Ask representatives to participate in information fairs, virtual meetings, and webcasts during which employees can ask specific questions.
  • Reach out to ERGs: Different demographics in your company may have specific concerns about their benefits that they may not want to share widely. That’s where employee resource groups (ERGs) can come in. If your organization has ERGs specifically for women, parents, LGBTQ employees, or multicultural groups, engage directly with these groups and give them a safe forum in which to ask questions specific to their interests.
  • Engage on multiple channels: People learn differently, so present employees with several options to access information about their benefits. Providing information in virtual meetings, webcasts, blogs, Slack messages, emails, and in-person Q&As can cast the widest net for grabbing the attention of as many employees as possible.
  • Offer a mobile platform: Make sure your benefits selection portal is optimized for mobile devices to maximize selection opportunities across your workforce.
  • Create interactive resources: It’s not very costly to provide employees with easy-to-use tools that can support their decision-making and relieve you from having to answer a deluge of individual questions. Give employees access to an online benefits calculator and comparison charts to help them more easily evaluate their options.

5. Train your team and empower managers.

One of the most crucial things you can do to make open enrollment more user-friendly is to educate the staff members whom employees mostly are likely to turn to first with their questions. Few things are more discouraging to employees than spending time coming up with a list of their questions and then having their manager or HR contact say, “I don’t know” and end the conversation there.

To ensure that doesn’t happen, proactively arm your HR staff and your employer’s managers company-wide with the information they need to either address employees’ questions directly or to point them to recommend resources.

Of course, educating HR staff about benefits should be a no-brainer. But you’d be surprised how often they cannot answer these questions, since HR employees in larger companies often specialize in specific areas and may not be knowledgeable about benefits options.

Educating managers may seem less obvious. But since employees often go to their supervisors first with their questions, managers should at least be armed with one-pagers and FAQs that can address the most commonly asked questions. If they can’t answer a question, they should know the resources or people they should direct their employees to.

It is your responsibility to put these teaching aids into the hands of all HR team members and managers before open enrollment begins.

True Measures of Success

According to Jamie Madden, senior vice president of workforce engagement and benefits connectivity at MetLife, “Understanding benefits leads to more informed open enrollment decisions, better utilization, and a happier, more stable, and generally more satisfied workforce.”

The data backs him up.

According to the 2023 Metlife Employee Benefit Trends Survey, 76% of workers who understand their benefits are happy with their choices, and 82% believe their benefits give them a greater sense of overall stability.

Providing efficient, thorough education about benefits is crucial to keeping employees happy with and loyal to their employers, which leads to the long-term retention of the quality workers companies most value.

HR is crucial to making that happen.

 

The information contained in this site is provided for informational purposes only, and should not be construed as legal advice on any subject matter.

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