Business leaders, the season’s shifting – and so should your focus. Open enrollment will be here before you know it. Are you ready to guide your employees through it?

For most employers, open enrollment takes place in October and November. And with today’s increasingly dynamic workforce, it’s more important than ever to get it right. A competitive employee benefits package remains one of the most compelling retention tools that employers have.

That’s why now is the time to plan for open enrollment 2025. These 10 tips can help you deliver your smoothest, most successful employee benefits enrollment season yet.  

Before You Get Started/The Pre-Planning Phase

A mistake employers can make is assuming the same benefits from last year will still appeal to this year’s workforce. However, employee expectations are constantly changing and, with a younger generation, personalization has become essential in the workplace.

This is where data becomes an HR leader’s best friend.

Take a close look at how your team used their benefits over the past year. Are employees taking advantage of your health plan, dental, vision, or supplemental benefits? Are there gaps in coverage or requests that keep popping up?

This is your chance to:

• Evaluate what’s working and what’s not
• Explore new plan options that fit your workforce
• Identify cost-saving opportunities or bundling options
• Align your benefits strategy with employee needs and company goals

1. Start Early and Prepare the Data (and Your Team)

While veteran employees will know it’s open enrollment season, it’s still beneficial to announce it—and with a bit of fanfare. This is your chance to build excitement, boost engagement, and make employees feel like they’re part of something important. Think of it as a mini internal campaign. Posters, countdowns, teaser emails, or even a kickoff event can go a long way in creating buzz.

And the best way to get started with anything exciting? Starting early! An early start of 60-90 days gives you time to meet with your benefits broker or PEO, evaluate your current offerings, explore renewal options, and get ahead of potential plan changes or cost increases. Early action means more choices, better communication, and fewer last-minute surprises.

Starting employee communications during planning can also be key. You don’t have to dive into the specifics of plans just yet. Just let your employees know what to expect, how they will receive their materials, and what the timeline will be.

If you’re changing your enrollment process—even just a little bit—give them a heads up. The more prepared they are, the better.       

2. Communicate Benefits via Multiple Channels

Keep in mind: you may be communicating with up to four generations of workers, each with their own media preferences. An effective employee benefits enrollment strategy includes many forms of communication: email, intranet, print materials, group meetings, one-on-ones, texts, etc.  

You may also want to mail at least one announcement letter or postcard to your employees’ homes. This will get their attention while bringing spouses and partners into the fold. 

3. Highlight What’s New

Adding new voluntary benefits? Tweaking your health plan? It’s important to call attention to changes upfront, especially those involving premiums and plan design. For most employees, open enrollment can be somewhat overwhelming, so simplifying the information is very helpful. When it comes to talking about this information, keep in mind that you should:

• Use plain language, not benefit jargon
• Highlight what’s new or changing
• Offer side-by-side plan comparisons
• Provide multiple channels for support (HR, PEO partner, live sessions)

These are some of the most effective ways to explain new changes (and even older options) to your employees.

4. Make Sure Your Technology is Employee-Friendly and Ready to Go

Even with the right plans and communication, open enrollment can create administrative headaches if you don’t have the right systems in place.

Now is the time to:

• Ensure your HRIS or enrollment platform is set up and tested
• Confirm eligibility and classification for all employees
• Assign roles and responsibilities across your HR or admin team
• Set internal deadlines well in advance of final submission dates

Getting ahead of administrative issues will also help you find opportunities to explain potentially confusing infrastructure to employees.

5. Hold Enrollment 2025 Meetings

Hosting both in-person and virtual meetings is a great way to kick off your employee benefits enrollment campaign. Use these sessions to explain the more complex aspects of your benefits, answer employees’ questions and underscore that this is all for and about your workforce.

If your employees work onsite, consider hosting a lunch-and-learn or two – the promise of pizza is bound to boost attendance. Or, if your providers are able, hold a benefit fair, where employees can engage with them directly to learn more about their products. If you’re offering voluntary benefits, this is a great way to improve participation.

6. Make It Visual

Let’s face it: few people enjoy reading extensively about insurance, even when it’s their coverage. The more visual and interactive you make your communications, the better your message will come across. Try mixing in short videos, memes, infographics, and charts to convey your benefit offerings.       

7. Offer Incentives for Early Birds

If you really want to emphasize early enrollment, consider offering rewards to the first wave of employees who submit their enrollment forms. Something as simple as gift cards—say for the first 10 or 20 employees—will generate worksite buzz and create some positive competition. 

8. Provide One-on-One Consults

Holding group meetings is very effective, but enhancing them by offering optional one-on-ones ensures that every employee gets the support they need. It helps employees choose the right benefits for their situation while demonstrating that you value your people and are willing to go the extra mile on their behalf.

9. Get Ahead of Common Questions    

What is open enrollment for benefits? Can you change benefits after open enrollment? When do benefits start after open enrollment? These are very common questions—and your company may hear others specific to your plans. Instead of asking HR to field them again and again, why not create a Q&A that employees can refer to proactively?     

10. Request Employee Feedback

At its core, open enrollment is about supporting your people. Benefits are one of the most personal, impactful parts of the employee experience, and the way you communicate and deliver them sends a message about your company culture.

Take time to:

• Ask for feedback before and after enrollment
• Explain the “why” behind any changes
• Show how your organization is investing in employee well-being
• Offer personalized support wherever possible

It also pays to create an employee benefits survey so you can find out what benefits your employees are loving or lacking. It shows employees that you care—and you can use that valuable input to improve next year’s experience, so your open enrollment process will just keep getting better!

Planning a smooth, efficient employee benefits enrollment process takes a bit of time and effort, but it’s worth it—and your employees will appreciate it. If you’re looking for support, VensureHR provides not only access to comprehensive employee benefits but also expert guidance to ensure your open enrollment process is seamless and successful. Learn more. 

---