5 Tips To Streamline This Year’s Open Enrollment

HR professional woman preparing for open enrollment

Let’s be honest. No one really likes Open Enrollment. Leaving HR teams overwhelmed and employees frustrated and confused, it’s no wonder Open Enrollment is consistently ranked as one of HR’s top challenges.

However, it doesn’t have to be that way. In fact, there are quite a few things you can do to streamline this process. So with Open Enrollment deadlines right around the corner, here are 5 ways you can make this time of year less stressful.

Prepare Early

Depending on your business size and benefits offerings, it may take you anywhere from 4-12 months to adequately prepare for Open Enrollment. In the words of Benjamin Franklin,

By failing to prepare, you are preparing to fail.

So what exactly does preparing for Open Enrollment look like? To start, reflect on how Open Enrollment has gone in the past.

  • What has past success and failure looked like for you?
  • Create a to-do checklist and prepare a detailed schedule.
  • Consider what plan information you need.
  • What preliminary communications and post-enrollment surveys have you used in the past? Evaluate these – are there any parts of your process or messaging you can improve?
  • Which benefits are most and least successful? Does this give you any insights into changes you should make to your benefits offerings?


It’s nearly impossible to know exactly what your team thinks about your company’s benefits offerings and enrollment process based on observation alone. To get a more accurate picture, we encourage you to administer an employee survey for feedback on the previous year’s Open Enrollment to guide your strategy for the coming year.

Ask employees about the plans offered, communications, enrollment process, and any suggestions they have for the future.

To level up further, a great idea is to analyze responses by job description, salary, location, age, number of dependents, marital status, etc. This may reveal additional trends so you can fill in any gaps for worker groups and plan a more tailored communication strategy.

Targeted Communications

Speaking of communications, now it’s time to plan them! How have you written benefits communications in the past? If you’re like most businesses, you probably put together a single, novel-length email to the entire company. Maybe an additional reminder email.

It doesn’t take a mind-reader to guess how that went over.

The thing is, different employees have different needs.

For example, new employees may require more detailed information on offerings and enrollment instructions. Meanwhile, seasoned employees generally benefit from briefer communications highlighting changes from the previous year.

If you noticed significant trends from your survey analysis, you can even create more targeted communications with recommendations by employee demographic groups.

Top Tip: Date-based workflows are a great way to create and automate these targeted, recurring communications!

Bring in a Benefits Specialist

Another way to streamline your Open Enrollment process is to partner with a Benefits Specialist. These individuals not only better understand the benefits. They can also reassure employees, leading to higher enrollment rates – and bigger tax breaks for you!

If you choose to work with a Benefits Specialist, take full advantage of them by involving them in the communications preparation process. Ask for their insights to message enrollment instructions, define common terms, address FAQs, and create more “user-friendly” explanations of the options available.

Additionally, see if they have any calculators or plan comparison tools available. These can help employees more easily identify the best plan for them in the time crunch of Open Enrollment.

Go Paperless

If there’s a single top time-waster of Open Enrollment, it’s undeniably the paperwork!

Manually completing forms, deciphering handwriting, and going back-and-forth with employees and insurance providers over errors wastes everyone’s time. It’s also much harder to do this year with remote workers due to the pandemic.

As an alternative, take the plunge and go digital! Instead of a traditional in-person seminar with a box of doughnuts as the only highlight of the hour, host a webinar or Zoom call and provide your benefit plan information in electronic form. (Maybe even send an e-gift card for doughnuts to the first 10 employees who enroll after the webinar!)

Do some research on Benefits Administration platforms (ideally that integrate with your payroll platform) to find the best option for your business. You’ll save time, reduce errors, and improve employee satisfaction.

Additionally, when employees make their selections online, the system will automatically send employee elections to your insurance providers and add the deductions in payroll!

Top Tip: In some cases you may still need to mail a paper copy of your open enrollment guide to certain employees’ homes. Be sure to check the Department of Labor’s safe harbor guidelines for any electronic retirement plan communications rules that may affect you.

Helpful Reminders

To end, we’ll leave you with a few final reminders and best practices. First, remember that as stressful as Open Enrollment is for you and your HR team, it’s also stressful for your employees.

According to a study by Unum, 22% of employees are confused during open enrollment, 20% are anxious, and 21% are stressed. As you prepare for Open Enrollment, focus your energy on clearly addressing the real questions employees have about benefits enrollment:

  • Why do I need coverage?
  • What are my options?
  • Which option is best for my needs and lifestyle?
  • How much will this cost me per paycheck?

Be concise. Avoid confusing jargon. Leverage technology where it makes sense. And most importantly, prepare as early as possible so both you and your employees have enough time to digest the information.

What do you think?

Are you ready for Open Enrollment? During this especially stressful time of year, what are you doing to streamline your processes for 2022 enrollment? Let us know in the comments below!

If you’d like some help automating benefits administration and Open Enrollment at your organization, then let’s talk! Our software is paperless, automatically adds deductions, and can significantly reduce the burden on your team.

Plus, our HR Services Department is always available to answer any additional questions you may have. Finally, don’t forget to follow us on FacebookTwitter, and LinkedIn for even more business tips and news.

Photo by Edmond Dantès from Pexels

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