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6 Simple Ways to Improve Open Enrollment

July 14, 2025

Two open enrollment for benefits forms with a woman out of focus behind them.

​It’s that time of year again. There’s a crispness in the air combined with an energy that is simultaneously exciting and scary. As the shadows cast longer and the kids head back to school, HR professionals face their own annual ritual: It's open enrollment season.

If you’re like many of your colleagues, you confront this yearly exercise with a mixture of enthusiasm and dread. It’s a busy time that is undeniably stressful and exhausting, yet it also gives HR an opportunity to make vital contributions to the business and to help people navigate decisions that will significantly impact them and their families.

Here are some tried-and-true tips to make the most of this crucial time.

1. Get Employees Ready

​The annual benefits-election process starts well before any forms are filled out. Employees shouldn't be asking basic questions about their coverage options in open enrollment meetings — that should happen before open enrollment occurs.

Provide materials and important information such as cost increases ahead of time so individuals can review their options and formulate questions before open enrollment begins. Delivery of these materials can occur through all available channels, including any online portals maintained by the employer or by insurance carriers, brokers, consultants and other vendors. 

Employees want to know four things for each program:

  • Why do I need the coverage?
  • Which features fit my needs?
  • What value does the program provide?
  • How much is this going to cost me per paycheck?

While the latest technology often gets a lot of attention, don’t overlook more inexpensive — and effective — methods to prepare and engage employees. Easy ways to get their attention include by putting notices in paycheck envelopes and making videos in English and Spanish available via YouTube or Facebook or on screens in offices and cafeterias. 

Alternatively, try creating a one-page information sheet that defines key terms and publicizes contact names and numbers, important websites, and a list of all the information needed to complete required forms.

Specialty Credential: Total Rewards

2. Keep the Focus on People

​While technology is changing how employees learn about and choose benefits, remember that open enrollment remains a people-oriented process.

Enlist the help of key “influencers” — that is, certain individuals who hold a lot of sway over their peers. These are people other employees go to for advice, with work-related questions, and for friendly or pick-me-up conversations.

Target communication to that office with the influencer in mind, then follow up to find out how these key individuals feel about the process and to determine what other employees are saying about it.

​3. Identify Your Workers' Needs

Review the results of previous years’ open enrollment efforts to make sure the process and the perks remain relevant and useful to workers. How effective were various approaches and communication channels, and did people give any feedback about the process itself? Ask these questions:

  • Where are employees finding information? 
  • What were their top 10 questions? 
  • What's new for this year?

For employers to innovate and improve the process, they need to understand their employees. Every workforce is unique, and what makes your group special will largely determine how best to manage the process. 

Employers can slice and dice their data to develop personas that represent different subsets of their population and then craft specific messages to each persona.

Tailoring open enrollment materials to these employee segments is crucial. If you have a large percentage of single, early-career-stage Millennials, for example, don’t build all your sample calculations around a family."

Customize information sessions and webinars to specific groups. They do not necessarily have to be defined by age or gender; categorizing by benefits status makes the most sense. For example, you might offer information sessions for people buying single coverage or spousal or family coverage.

4. Keep Things Simple and Clear

Be careful of engagement for engagement’s sake, and ​don’t overwhelm the workforce with repetitive communications. For each effort you consider, ask yourself, “Does it convert to meaningful action and help people understand their benefits and how they work?”

Focus on communicating early and often, starting in September for open enrollment in mid-November, even if insurance premium rates are not yet available.

Quiz: Open Enrollment Practices in the U.S.

5. Make It Easy to Ask Questions

A personal touch is also important, so some HR executives and their staffs make sure they show up at remote worksites to answer questions about how to maximize the available plans and the tools and resources the company provides.

By expanding the duration of open enrollment, you can have available to employees for individual 20-minute sessions to discuss their unique benefits questions and concerns with HR. Some leaders were concerned that people might avoid choosing those plans simply because they did not understand them. 

Although group meeting to explain benefits is a tempting option, but it does not encourage conversation because employees are less likely to ask questions about their specific needs.

6. Offer Enrollment Incentives 

​Of course, nothing gets people’s attention like free stuff. To encourage employees to sign up for benefits as soon as possible, hold a raffle on every day during open enrollment, with workers entered only after they have completed their paperwork. If they finished their paperwork the first day, their names are in the raffle for two weeks during the enrollment period.

Considering holding a virtual benefits fair where individuals can go online to get more information about specific benefits programs. Then, send gift bag to all workers with the merchandise they would have received at an in-person fair. 

Podcast: Get Ready for Open Enrollment

7. Leverage All Available Resources

​Budget constraints are a reality for every company. To maximize available resources during open enrollment, savvy HR and benefits executives look for partners inside and outside the organization.

It's not unusual for HR to partner with marketing, who can contribute graphics and copy to make e-mails more compelling.

Brokers, insurance carriers and other vendors can also be important partners, especially for smaller organizations that may not have a lot of internal staff to help with the process. A broker can be available when employees want to discuss sensitive topics and questions with someone outside the company.

8. Get Spouses Involved

​Benefits enrollment is a family affair, so include spouses in informational sessions. These meetings can be held after work hours and on weekends when they are more likely to be able to attend and can ask their own questions. If you have the space and personnel, employers can allow kids to attend with a room and an attendant where they can color, watch movies and so on.”

If in-person meetings are not possible, offer evening or weekend webinars so that spouses can be more involved. ​However, you may need to provide additional support for some spouses, including expanded foreign language options in communications and enrollment forms. 

Benefits enrollment strategies are always evolving. What worked last year may not be relevant this year — but you can’t go wrong by putting employees’ needs first.  

Total Rewards
Total Rewards Strategy

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