Skip to content
Humanized Work

Open Enrollment Success: Strategies for a Stress-Free Season

Discover expert tips to streamline open enrollment, reduce stress for employees and HR teams, and ensure a seamless benefits season.

Woman sitting down going through benefits paperwork

Open enrollment. Traditionally one of the most stressful times of the year both for employees and People + Culture teams.

But it doesn’t have to be that way! We’re sharing our best tips for a breezy open enrollment for all!


We Get It, Employee Benefits are Expensive!

Benefits are one of the most expensive investments a lot of employees make, but in most cases, very few actually understand what they’re being offered or how to take advantage of them. Couple that with fast education that comes at them once a year, and you get stress, confusion, overwhelm, panic… you name it.

And our beloved People + Culture teams–with already-full plates, adding on communication updates, scheduling, organizing, and running multiple meetings, system updates, reporting, meeting with employees (and sometimes spouses) to answer questions; all the nuances that go into pulling off a successful enrollment–we see you.


How Does Open Enrollment Work? Breaking It Down

Open enrollment comes down to just three things executed really well:

  • Communication
  • Education
  • Data transfer

That’s it. Just those three things! Everything else is a bonus.


1. Building a solid communication plan for your employees

Building out a communication plan for open enrollment is the key to ensuring everyone has the information they need in the right medium. Taking the extra steps to translate materials and send out the same communications in multiple methods is well worth it to make sure absolutely everyone knows exactly what’s coming and when. Some of our best tricks:

  • Clearly Outline Changes: Be painfully, obviously clear about what’s changing and what’s new. If there are cost increases, tell employees about them so they can budget. If benefits are changing or going away, say so.
  • Keep it Simple: Keep it short, sweet, and to the point. You will lose people after the first few sentences, so bullet points are your friend here.
  • Get Creative: Involve your marketing team (or creative agency) to make your messaging pop! Bright colors and animated graphics – grab that attention!
  • Overcommunicate: It’s almost impossible to over-communicate during open enrollment. If you think you’ve sent too many messages, emails, or home mailers and posted too many posters around the office (with a QR code to the enrollment site if you’re savvy), you haven’t.
  • Plan Ahead: Schedule send your emails! Save yourself the headache, and schedule emails to auto-send ahead of time. Sure, it takes a few extra minutes on the front end, but what a feeling it is to see your email send itself without your involvement on key dates.
    • If your internal chat/messaging systems allow for it, schedule send those messages too!
  • Send Frequent Reminders: Add open enrollment to everyone’s calendar with reminders for the first day, the midpoint, and the last day. A company-wide calendar is great, but if someone doesn’t opt in, they’ll miss key dates.
  • Share the Meeting: Add all open enrollment meetings to everyone’s calendars, and consider inviting spouses (and domestic partners, as your plan allows). They usually have a vested interest and may have questions.
    • Pro tip: Enable closed captioning at the start to ensure everyone can understand the communication. Don’t wait for someone to ask.
    • Ask your broker if they can record (sometimes they can’t, depending on what information is getting shared). Make the recordings available on demand so people can watch as many times as they want and at the times that work best for them.
  • Language AccessibleHave a multi-lingual workforce? Ask your broker if they can support open enrollment in other languages; if not, consider hiring a translator, hosting language-specific sessions, and providing materials in their native language. It is a small investment, but very worthwhile to make sure your employees fully know what’s being offered.
  • EOI Forms: Include a link to the EOI form or a copy of the EOI form itself in your communication. The goal is to make it as easy as possible for everyone to do what’s being asked.

2. Educating your employees will lead to informed decisions

If you’re already in open enrollment and haven’t been doing education all year, don’t panic. You can still provide meaningful information that helps your team in a short period! The key is to focus on what your team needs to know to make the best choices for themselves and their families. Think about things like what common terms mean and what to consider about each plan.

  • Be Succinct: Again, keep things short and sweet. People have very limited time, so any material you provide must get to the point.
  • Leverage the Power of Video: You can offer video on demand, and people can watch as often as needed while making their selections. Add captions to your video to help people who may not hear well or prefer to read along. 
  • Eliminate Jargon: This is a great area to partner with the marketing team, especially if you have copywriters. If they need help understanding the content you're creating, chances are everyone else will too, so it always helps to have non-benefits/non-People + Culture team members review before posting.
  • Ongoing Benefits Education: Longer-term, consider embedding regular, ongoing benefits education throughout the year. Quick messaging with fast facts, highlights of your plan features, how to make the most of your plans, free perks offered with your plans, and what terms mean (and how it applies to them) are great ways to provide digestible amounts of information in real-time that add value for your people.
  • Work with Your Broker: Partner with your broker to see what resources they have available that you can leverage!

3. Making sure the data transfer is error-free!

The communications have been sent. The education has been delivered–you’re almost there! The last key piece is a seamless, flawless data transfer. No matter how your open enrollment information gets to the carriers, this is where the rubber meets the road. You want to double-check, actually, make that triple-check the information is accurate and complete. If you followed along with our checklist, you should have plenty of time to adjust if you find any errors.

A great way to ensure things are accurate is to send personalized confirmation statements. Many benefits administration platforms provide these to employees – spectacular for you if the system allows you to PDF and distribute to everyone, asking them to confirm. If not, no worries. You can create a Word document template, run a report out of your system, do a mail merge to create personalized statements, and then distribute (just make sure you check these – we don’t want to share one person’s information with someone else). Some key things we’re looking for: 

  • Re-Enrollment in FSA and HSA Plans: If employees had FSA and HSA plans last year and didn’t select one for this year, it’s wise to follow up with them and ensure that’s correct.
  • Vast Differences in Plan Selection: If they had platinum last year and are election bronze this year, or vice versa, check in with them. If they had dental, vision, life, etc. last year and don’t this year, check in with them.
  • Not Yet Enrolled: If you hosted an active enrollment and see people who didn’t enroll one way or another and didn’t actively waive benefits, check in with them. The time to discover they missed hitting the “submit” button is not when they’re at the doctor’s office three months from now.
  • Accurate Codes: Ensure all of your deduction codes align with the deduction codes in your benefits administration system, and ensure you have the correct date for the new deductions set up.
  • Issuing of Cards: Confirm that your changes were received and when your people can expect their new insurance cards (pro tip: proactively communicate this – it tends to be the most frequently asked question once open enrollment is over! Even better if people can access it digitally).
  • Run a Mock Payroll: Before the first payroll with the new benefits deductions, run a mock payroll and compare it against your open enrollment data to ensure everything looks correct and that there are no duplicate deductions, old deductions have stopped, etc.

And that’s a wrap!

So, Why Partner with livingHR? 

If you’re already sweating reading this, know you can reach out to us at any time, and we’re more than happy to jump in and provide an extra pair (or two, or three, you get it) of hands! We can create full communications plans, including designed posters, mailers, and other announcements. We can partner with your broker to do the heavy lifting, so you don’t have to. We can create pre-and-post surveys to identify what employees want and how open enrollment went from their perspective. We can help you identify and set up ways to track metrics to validate plan success. And we can create a full suite of microlearning videos customized to the benefits you offer that provide straightforward information to your people.

Happy Open Enrollment!

New call-to-action

Alexia Benner (she/her)

We humanize work for everyone because we know it creates better outcomes for humanity and business.


Subscribe to Our Newsletter

Get updates on the latest blog releases and resources to humanize the workplace!

Latest Articles

6 Effective Recruitment Strategies to Implement in 2024

6 Effective Recruitment Strategies to Implement in 2024

We uncover the top recruitment strategies to implement in 2024 and we discuss the importance of talent retention.

AI and the Future of Work: How to Become a Better People Leader

AI and the Future of Work: How to Become a Better People Leader

Read on as we uncover the essential insights and skills necessary to lead effectively in the age of AI.

People Analytics: 6 HR Metrics That Matter to Leaders

People Analytics: 6 HR Metrics That Matter to Leaders

HR metrics are very important to track and crucial for people leaders. Here are the top 6 metrics to lookout for.