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Best Practices for a Smooth and Stress-Free Open Enrollment

A mature male business owner reviewing paperwork while sitting at desk in an office
October 3, 2025
5 min. read

When you run a small business, every decision you make matters, especially when it comes to employee health benefits. For many companies, open enrollment is one of the most important times of the year. It’s when your employees can choose or update their health insurance coverage, giving them the opportunity to make decisions that directly impact their well-being and financial security.

But here’s the catch: open enrollment can also be confusing, stressful, and overwhelming if it isn’t handled the right way. From unfamiliar terminology to tight deadlines, it’s easy for employees to feel lost. For small business owners, that means it’s critical to provide guidance, clarity, and support during the process.

Open Enrollment Best Practices: How to Communicate with Your Team

To help you get started, we’ve pulled together some open enrollment best practices that will ensure communication with your team runs smoothly and successfully for a great experience all around. These strategies not only help your employees feel supported but also strengthen your business by boosting satisfaction and retention.

1. Start Planning Early

The number one rule of open enrollment? Don’t wait until the last minute. Small businesses often don’t have the luxury of a large HR department to handle logistics, so proactive planning makes a huge difference.

Give yourself plenty of time to review your benefits offerings, confirm ACA compliance, and make any changes to your health plans before the enrollment window opens. If you work with a benefits management service like Meridio, we’ll guide you through these steps so you know you’re offering affordable, compliant options.

By starting early, you avoid rushing and your team has more time to understand their choices which leads to better decisions and fewer headaches for everyone.

2. Keep Things Simple

Health insurance terms can feel like alphabet soup to employees. HMO, PPO, deductible, coinsurance, it’s enough to make anyone’s head spin.

One of the best ways you can support your team during open enrollment is by simplifying the process. Break down complicated topics into plain language, offer examples, and avoid unnecessary jargon. If you need a refresher, check out our blog Understanding the Jargon: Healthcare for Small Businesses. Think of it as teaching, not just informing.

For example, instead of saying: “This plan has a $1,500 deductible and 80/20 coinsurance after that,” you might explain: “With this plan, you’ll pay the first $1,500 in medical costs yourself. After that, your insurance pays most of the bill, and you’ll cover 20%.”

Clear explanations help your employees feel confident in their choices, rather than overwhelmed.

3. How to Communicate with Your Team

Even the best health benefits plan won’t help your employees if they don’t understand it. That’s why communication is the cornerstone of a successful open enrollment.

Here are a few strategies that small businesses can use to improve communication:

  • Host an informational meeting: Give your team the chance to hear about their options in a group setting, then open the floor for questions.
  • Offer written resources: Provide a simple one-pager or FAQ document that outlines the key details of each plan.
  • Use multiple channels: Don’t rely on one email. Share information through meetings, flyers, your company intranet, or even short video clips.
  • Check for understanding: Encourage employees to reach out with questions and provide a clear point of contact for support.

The more open and accessible your communication, the smoother the entire process will be.

4. Highlight What’s New or Different

If you’re offering the same plans as last year, employees may assume nothing has changed. But if there are updates—like new ACA compliance rules, pricing adjustments, or added benefits—it’s important to highlight those clearly.

Make it easy for your team to see what’s different from last year so they don’t miss out on changes that could save them money or better fit their needs.

5. Provide Tools and Support

Your employees want to make the best decision for themselves and their families, but it isn’t always easy to compare options. Consider offering tools or support that simplify the process.

This might include:

  • Cost calculators to estimate expenses under different plans
  • Side-by-side plan comparison charts
  • Access to a benefits specialist who can answer individual questions

Meridio, for example, provides hands-on support for small businesses and their employees during open enrollment, ensuring every person has the resources they need to make confident decisions.

6. Encourage Employee Engagement

Open enrollment isn’t something employees should put off until the last day. Encourage your team to engage early and often.

Send reminders as deadlines approach, share helpful tips, and stress the importance of reviewing their options thoroughly. When employees understand the stakes and feel supported, they’re more likely to take the process seriously and less likely to run into problems later.

7. Partner with a Benefits Management Service

As a small business owner, you already wear enough hats. Managing open enrollment shouldn’t add more stress to your plate. By partnering with a benefits management service like Meridio, you’ll have access to expert guidance, affordable health benefit options, and support throughout the entire process.

From keeping your business ACA-compliant to handling the administrative side of open enrollment, Meridio helps you focus less on paperwork and more on growing your business.

Make This Year’s Open Enrollment a Success

Open enrollment doesn’t have to be complicated. By starting early, simplifying the process, prioritizing communication, and partnering with a trusted benefits management service, you can make it easier for your employees and yourself.

Want to dive deeper? If you’re still exploring how to roll out benefits for the first time, check out our blog 👉 How to Introduce Health Benefits to Your Employees

Or, if you’re ready to see how Meridio can help streamline open enrollment for your business, let’s talk 👉 Connect with our sales team today

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