By: Debra Kabalkin on October 19th, 2023

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The Employer’s Guide to Surviving Open Enrollment

Total Rewards | HR compliance

The annual open enrollment period is one of the busiest times in your HR calendar. Everyone involved will have to handle queries, process requests—and firefight the occasional crisis.

Getting open enrollment right is an essential part of your overall employee experience. Benefits changes are a big deal for your team, and they need to know they can trust you to care for their needs. Errors with things like tax credits, monthly premiums, eligibility, or health insurance coverage could damage employee relationships, ultimately affecting staff retention.

But don’t worry. With the right planning, you can survive open enrollment season while providing a first-class experience for your team.

What is open enrollment?

Open enrollment is the window during which employees can make changes to benefits such as health insurance. The Federal Open Enrollment period begins at the start of November and runs through to January. Private employers may opt for a different time of year, although it’s common to begin open enrollment during the fall.

Whenever your open enrollment window begins, one thing is for sure: it’s going to be a busy time for your HR team. Open enrollment involves a huge amount of coordination, both with benefit providers and the employees themselves.

A strong HR team with solid processes can help your company get through enrollment without any hitches. We recommend thinking of open enrollment as having three distinct phases:

  • Before open enrollment, when you confirm benefit details and prepare to communicate with staff.
  • During open enrollment, when you help employees fine-tune their benefits, while also managing documentation and compliance.
  • After open enrollment,  a time for analysis, optimization, and resolving any issues that arose during the window.

Let’s take a look at what you need to do during each phase.

What to do before open enrollment

It’s never too early to start preparing for the next open enrollment window. Here are some essential tasks for you and your HR team in the run-up to enrollment.

1. Analyze last year’s feedback

Feedback from last year’s open enrollment window will help you identify success that you can build upon, plus the issues that you need to address. Some of the data to consider includes:

  • Employee feedback: Use short surveys to gauge employee reactions. Are they satisfied with their new benefits coverage? Did they have any issues with the process?
  • Managerial feedback: Local leaders can tell you a lot about open enrollment, as they’re often the ones fielding questions about benefits. They can also help you understand how benefits impact on team engagement and retention.
  • Compliance reports: Watch out for any issues that may have arisen from benefits enrollment. Talk to your compliance team and ask if they have any notes for the next window.

2. Learn more about employee requirements

Employee requirements change constantly. You might have a young team that is focused on fun perks and professional development opportunities. But, when they age, they might have a greater need for family healthcare plans and childcare benefits.

Stay ahead of changing requirements by talking to your team about their requirements. You can use surveys to ask questions like:

  • Are you happy with your current benefits?
  • Do you feel you have an adequate selection of benefit options?
  • What additional benefits would best support your needs?
  • Do you intend to make changes during the open enrollment window?

3. Schedule benefit planning meetings

Key players, including the broker representative, senior human resources, and finance leadership, should have a pre-open enrollment meeting, typically during the late summer months.  The meeting should discuss things like:

  • Upcoming changes to benefits, including rate increases
  • Employee satisfaction with current benefit offerings
  • Communication strategy for open enrollment
  • Compliance issues, i.e. ACA compliance for health insurance benefits

4. Develop a communication strategy

Open Enrollment InfographicCommunication is the most important part of open enrollment. Your team needs clear information about what’s on offer and how to find the right Total Rewards for their needs.

HR and local leaders can work together on a communication strategy. Here are some of the main things to plan for:

  • Benefit selection guides: Employees should have access to the information they need to make a decision. This could mean health plan brochures, benefit selection guides from your broker, or an online comparison tool.
  • FAQ: Employees will have many questions about their benefits. You can streamline the process by anticipating those questions and creating a detailed FAQ that provides clear answers.
  • Inclusion: Remember, not everyone is in the office. Remote employees and COBRA beneficiaries might miss out on essential communications, so you need a strategy to include them.

What to do during open enrollment

Open enrollment involves two vital tasks: helping employees choose new benefits, and then implementing their changes. Most of the time, this runs smoothly, but there are some important tasks for your HR team.

1. Follow an active enrollment or passive enrollment strategy

Companies can take an active or passive approach to open enrollment. The main differences between the two are:

  • Active enrollment: The company asks each employee to confirm their benefits during the open enrollment window. Active enrollment can lead to higher benefit uptake and increased employee satisfaction, but it also creates a substantial workload for the open enrollment team.
  • Passive enrollment: Employees automatically continue on the same benefits unless they opt to make changes. Passive enrollment is a more efficient approach to enrollment, but there is a greater risk that employees won’t switch to benefit options that suit their current needs.

2. Provide a point of contact

No matter how well-organized you are, there will always be some difficult questions. It’s good to have a point of contact that can handle questions from employees or their managers. In some cases, these questions might require a response from the benefits provider.

Some tips here include:

  • A help inbox: Create a dedicated email address, such as, and get your benefits team to check it regularly.
  • A phone line: It’s great if employees can pick up the phone and call someone with benefits questions. You could organize a rota so that benefits experts can take turns answering calls.
  • A Slack/Teams channel: Build a dedicated space where people can ask questions. A public channel on Slack or Teams will allow people to share information and learn more about their benefits options.

3. Respond to issues

Things can go wrong, so it’s important to respond as soon as possible. Your team might benefit from a tier system for dealing with any issues. When one tier can’t resolve the problem, they escalate to the next tier:

  • Tier 1: Minor issues, such as correcting errors and answering common queries.
  • Tier 2: Larger issues that require managerial intervention, such as compliance problems.
  • Tier 3: Problems that require high-level intervention, such as problems with the benefits broker.

What to do after open enrollment

The window is closed, and employees have moved onto their new benefit schedules. They can forget about open enrollment for another year.

Sadly, you and your HR team can’t forget. There’s still a lot of work to do, with tasks such as:

1. Issue new documentation

There’s an urgent need to issue some documentation, especially Evidence Of Coverage for healthcare plans. While most of this should happen automatically, you may need to chase the provider in some cases. Make sure to allocate some time after the window for confirming documentation.

2. Reconcile insurance invoices

You need to reconcile employee changes with incoming insurance bills. As each insurance bill arrives, check the employee listing against the revised employee elections that were made during Open Enrollment. Make sure the employee is in the correct plan with the correct dependent coverage and take swift action on any errors.

3. Review payroll deductions

Review employee deductions to ensure they are applied accurately. If an employee has been overpaid or underpaid, then the first step is to speak directly to the employee. Explain the error and agree on adjustments to their upcoming paychecks. It’s a good idea to confirm these adjustments in writing and store the written confirmation in their benefits plan. Make sure to send this written instruction to the payroll team so they can implement their changes.

4. Verify compliance

Healthcare benefits may involve a lot of compliance work, including issues related to the Affordable Care Act (ACA), ongoing coverage for former employees (COBRA), and Medicare/Medicaid. Check in with your internal auditing team to verify that they are satisfied with all activity during open enrollment. If you discover any regulatory breaches, gather all relevant paperwork and speak to your compliance expert about next steps.     

5. Gather employee feedback

Now that this window is closed… it’s time to think about the next window! This is an ideal moment to conduct employee surveys, especially about the enrollment process itself. Ask them if the system was user-friendly, if they understood their options, and if they’re happy with their new cover.

Make open enrollment a success

Open enrollment is a vital part of your broader HR strategy. It's a chance to check in with employees, assess their satisfaction with their Total Rewards, and look for opportunities to improve engagement.

Sure, it's a lot of paperwork. But it can be productive if you approach it the right way. 

Looking for some help with compensation strategy and employee experience? Book a call with a Helios HR consultant and let's talk about how our expertise can benefit you. 

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