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Navigating open enrollment can be tricky, even for seasoned human resource professionals.

I’ve experienced firsthand the many challenges HR professionals face during open enrollment.

Between managing benefit renewals, vendor partnerships, and system requirements, the biggest obstacle we face is keeping employees engaged in the enrollment process.

So, does open enrollment have to be complicated? No, we can take proactive steps to ensure our teams are set up for success. 

As a seasoned benefits professional with 12+ open enrollments under my belt, I’m happy to share some best practices and tips to transform your company’s open enrollment experience.

What Is Open Enrollment And How Does It Work?

The annual open enrollment window allows your benefit-eligible employees to newly enroll, modify, or drop your company’s benefit plan options for the upcoming plan year outside of having a qualifying life event or other special enrollment period.

Benefit options typically include a combination of employer-sponsored plans such as:

  • Health Insurance plans—Health Maintenance Organization (HMO), preferred provider organization (PPO), or high deductible health plan (HDHP)
  • Vision and dental coverage
  • Tax advantage accounts—Flexible Spending Accounts (FSA), Health Savings Accounts (HSA), Health Reimbursement Accounts (HRA)
  • Disability and Life Insurance.

The annual open enrollment window takes place during the fall and can run anywhere from two to four weeks, though this can vary by organization.

For employees, missing this window could result in losing health coverage or getting stuck with benefits that don’t meet their current needs or those of their covered dependents/beneficiaries.

This could mean them having to pay out-of-pocket for essential medical care or having to forgo seeing a medical professional altogether.

This is why engaging employees is so critical to ensure they properly understand and take advantage of the benefits enrollment.

5 Steps To Prepare For A Successful Benefits Enrollment

Plan ahead 

For employees, open enrollment planning can seem as easy as a magician pulling a rabbit out of a hat, while for HR professionals it often feels like a circus juggling act. 

During this time HR professionals wear many different hats: we are negotiators, strategists, educators, project managers, and implementation specialists.

Creating a detailed project plan will help you balance the various deadlines, action items, milestones, and partnerships to ensure a smooth open enrollment go-live.

As best practice, your enrollment planning should start no later than 3 months prior to your desired enrollment period

Planning should be a collaboration between you, your brokerage team, and benefit providers.

With organizations struggling to keep up with rising healthcare costs, it’s imperative that you partner with your brokerage team to evaluate benefit renewals.

During these conversations, your brokerage team will present year-to-date benefits usage data, which will help you determine if your benefits package adequately supports your population or if improvements are needed.

Should you find any gaps in your benefit offerings, this is the time to strategize on plan design changes, new benefit offerings, or new vendor partnerships.

During this time you will also want to meet with your benefits providers to outline any system requirements if using benefits management software and note key deadlines for post-enrollment file deliveries.

To help facilitate these conversations, leverage your brokerage team as they can coordinate these meetings on your behalf.

Once benefit renewals and plan designs are finalized, you can begin working on a communication and benefits education plan to ensure clear expectations are set and tools are provided to employees so they may proactively get ready to take action for the upcoming open enrollment.

Establish an efficient communication plan

One of the most common challenges employers face during open enrollment is employee engagement

For HR professionals, it can feel like no matter how much you try communicating with colleagues you can’t garner their attention.

On the other hand, some employees I’ve spoken to shared a feeling of information overload which led them to distance themselves from the process. 

As such, I’ve found that an effective communication strategy will do the following:

Set clear deadlines and expectations early on

With employees focused on their day-to-day tasks, providing them with a detailed timeline of dates and actions required at least two weeks before your chosen enrollment start date will help them manage their time better. 

Communications should also specify when benefits elections will become effective and what happens if they fail to take action. 

Highlight major benefit changes and new benefit offerings

As employees go through the open enrollment process, the most common question they ask is, “Will my benefits change?”.

Making benefit changes a focal point for employees during open enrollment ensures they won’t miss the opportunity to enroll in a benefit that better serves their needs and those of their covered family members.

Ensure open enrollment information and resources are easily accessible 

Utilizing tools like your company’s intranet or virtual messaging board as a centralized hub for all your open enrollment resources can ensure employees know how to easily find and access information.

Leverage various modes of communication

Communication styles and preferences vary—some employees predominantly use email while others prefer instant messaging, etc.

In order to ensure your communications reach all employees it’s imperative to utilize multiple channels of communication.

Here are some examples:

  • Email
  • Intranet
  • Messaging communication channels (such as Slack)
  • Internal Social Media Sites
  • Employee handbook.

Target communications to your population

While all employees should be sent the initial open enrollment communications and resources, it will be important to target reminders and follow-up communications to employees who have not yet taken action.

This will reduce confusion among employees who have completed the requested actions in a timely manner while also ensuring employees who have yet to take action are aware of the upcoming deadlines. 

If you’re utilizing benefits management software, you can easily run enrollment status reports to keep track of employees who may need a follow-up and automate reminders. 

If communication is done right, employees will be more engaged with the process and ultimately feel more in control of their benefits.

Empower employees with the use of education

While benefit offerings are a huge recruiting and retention tool, employees struggle to understand how their benefits actually work. 

In fact, according to Metlife’s 2022 benefit trend study, 35% of employees feel the benefits information provided by their employer leaves them with more questions than answers. 

While we may understand terms like copay, deductible, coinsurance, and out-of-pocket maximum, the truth is most employees aren’t familiar with these terms.

This lack of understanding about how health benefits work can add to the sense of stress when faced with making decisions during open enrollment.

Benefits education doesn’t have to be hard, what is crucial here is to meet your population right where they are. 

In preparation for your open enrollment, sending out a benefits survey can be a great way to collect feedback from employees about their understanding of your company's benefits package.

The information collected should drive your benefit events and resource planning. We all digest information differently so make sure to provide your employees with a variety of educational options, this can look like:

  • Benefit office hours
  • Information sessions (virtual, in-person, or both)
  • Benefit/Enrollment webinars
  • Online & Printed Resources (i.e. open enrollment guide, plan summary of benefits, etc.).

I recommend you leverage your benefit brokerage team and your providers. A lot of the time they’re able to host information sessions or provide you with a wide set of benefit resources you can share with your population.

Providing employees with educational opportunities and tools can empower employees to take action while also cultivating an understanding of the value of their benefits package. 

Leverage technology where possible

Gone are the days when paperwork ruled the open enrollment process. Benefits administration software can automate open enrollment from start to finish. 

These tools help streamline the open enrollment experience by allowing HR teams to build their own one-stop shop where benefit plans are managed, benefit enrollments are captured, employee engagement is tracked, and enrollment files are sent directly to insurance carriers to ensure carrier sites reflect updated benefit enrollment information. 

Not only does benefits administration software make employer’s lives easier, it also makes the overall process of electing benefits for employees less overwhelming due to the user-friendly experience.

On the employee-facing side, most benefits administration software gives employees access to a self-service portal where they can receive important deadline reminders, track open enrollment action items, and see their current benefit plans as well as any changes they make once they submit their open enrollment task.

Prioritize post-open enrollment work as much as early planning

Phew! The open enrollment period has ended and now it's audit time! 

Conducting open enrollment audits is crucial to ensuring a smooth start to the benefit plan year.

By taking the time to audit the enrollment data prior to it going over to your carrier sites, you can catch enrollment discrepancies and make timely corrections to ensure the most up-to-date data is loaded prior to the benefit's effective date. 

Once your enrollment audit has been finalized you should touch base with your benefit providers to confirm enrollment files have been received and processed. This will ensure employees receive their updated benefits ID cards as well as any required communication from carriers in a timely manner. 

Auditing your first invoices as of your plan start date can also ensure employee payroll deductions have been updated to reflect the new plan year elections.

Taking these precautions can lessen access to care complications once the new plan year begins and reduce the need for payroll corrections, ultimately leading to a seamless benefit transition.

Enrollment audits can also serve to get a better picture of what employee benefits are trending amongst your employees.

This information can be used to evaluate your benefits program and determine if changes may be needed next year.

To close the open enrollment season, it can be a great idea to send out a survey to collect feedback from employees on their open enrollment experience.

Data collected can help HR professionals evaluate their process and note improvements where needed for the next open enrollment. 

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Open Enrollment Best Practices

While open enrollment is a seasonal event, actions taken around this time can have a lasting impact on employee access to care for the following plan year.

By implementing these best practices, you can transform your employees' open enrollment experience. 

  • Start planning at least 3 months prior to your desired open enrollment period. The more time you have the better. 
  • Tailor open enrollment to your population, tools such as surveys can ensure decision-making reflects your population's needs. 
  • Leverage your broker and benefit provider teams as most times they have ready-to-share benefit resources and can facilitate information sessions
  • Communicate early and often; share important dates and benefits information at least 2 weeks prior to your enrollment start date and follow up with weekly reminders. 
  • Use multiple channels of communication. Take advantage of email, instant messaging, your company’s intranet, information sessions, webinars etc. Not everyone checks their email, by taking advantage of various modes of communication you make sure the information doesn't slip through the cracks. 
  • Automate where possible with the use of technology. With tools such as benefits management software, you can configure workflows to facilitate the enrollment process for employees while also monitoring the enrollment process to ensure employees stay on track.
  • Audit your enrollment files once the open enrollment window closes. This will guarantee enrollment discrepancies are found in time to make corrections prior to the plan year start.

Following the process and best practices above will put you in good stead for a smooth enrollment process. 

For any further help or guidance, find me in the People Managing People Community, a supportive community of HR and business leaders passionate about building organizations of the future.


By Camila Menendez

Camila Menendez-Santos is a Benefits professional with experience working with large to mid-size companies within the Tech industry as well as start-up environments. Her passion lies in sustainable benefit plan designs, benefits education, and policy creation to enhance the employee experience.