Charting a Course Through Open Enrollment Challenges

September 7, 2023

This Shepherd Insurance webinar delves into the quirky world of annual open enrollment, uncovering the fascinating intricacies of human behavior and decision-making. From missed deadlines to creative reasons for plan choices, we shared real-world experiences and optimal strategies to help you navigate this critical process more smoothly. Watch the recording below, or scroll down to learn from an industry veteran, Shannon Russell, Partner and Director of Employee Benefits at Shepherd Insurance, who has helped countless clients simplify the art of open enrollment. You’ll gain valuable insights and strategies that can make your next open enrollment a resounding success!

Watch the Webinar Here:


Insights and Strategies for Success

Open enrollment is a crucial period for both employees and employers alike. It is a time when employees can review and select their benefits for the upcoming year. For employers, it is an opportunity to communicate effectively, offer diverse benefits, and ensure a seamless process for all involved. Whether you seek comprehensive healthcare coverage, are planning for retirement, or are exploring flexible spending options, this is your moment to craft a roadmap supporting your aspirations. Here are some best practices to consider during open enrollment to make the most of this period.

Start Prepared

Stay one step ahead by familiarizing yourself with the benefits, delving into the fine print, and jotting down your priorities. This is your opportunity to be proactive, to envision your needs and aspirations, and to ensure that the benefits you select align seamlessly with your life. Gather your questions, engage with resources, and approach enrollment with readiness. 

  • What will make this year’s open enrollment a success?
  • What barriers could prevent my employees from acting?
  • What might I need to do differently from last year?
  • What do I need to include to help make open enrollment a success?


Engage Employees

96% of Americans need help understanding basic health insurance terms like deductible, coinsurance, copay, and out-of-pocket maximum. Engaging the employees meaningfully so they fully realize that understanding their benefit options and choosing the right plan is extremely important. 62% of Americans said they usually keep their health insurance selections the same because it is too stressful.

Popular engagement tools include:

  • Paper Information
  • In-person meetings
  • Intranet & social media messaging
  • Texts & mobile apps
  • Videos
  • QR Codes


Create and Follow a Communication Plan

It is essential to create a workflow to map or document the employee’s experience so you can better understand all the touch points to maximize the effectiveness of your communications. While employees would rather have benefits communication a few times throughout the year, 48% of employers only provide education during open enrollment. Your plan can be simple or complex, pick what is best for your organization and culture.  

Sample Simple Plan:

7 – 10 days prior to beginningOpen enrollment announcement with materials
1 – 3 days prior to beginningReminder open enrollment is almost here, with frequently asked questions and documentation
1st & 2nd day of open enrollmentReminder of open enrollment requirements and deadlines
1 – 2 days prior to endingReminder open enrollment is closing
Last day of open enrollmentNotice of closing

Clear and Meaningful Communication

Understanding your workforce’s makeup, learning styles, and benefits enrollment needs is important. That can be as simple as understanding what generations are present in your group, and for many of you, that is five generations. These generations and their habits include:

  • Traditionalists (pre-1946) – They are worried about running out of money and staying active. Connect them with an agent to discuss Medicare insurance options.
  • Baby Boomers (1946-1964) – This generation includes early adopters and is VERY resistant to change. They learn best by actively participating in a classroom-style meeting.
  • Generation X (1965-1996) – They seek multimedia or web-based training, bullet point briefs, and access to an organized database they can pursue.
  • Millennials (1981-1996) – The women are outperforming men in this generation. They seek help by connecting with interactive multimedia formats that are social media-based.
  • Generation Z (1997-2012) – They prioritize financial security over personal fulfillment. They likely won’t enroll in the medical plan, but they still highly value the offer.

Understand How Employees Are Communicating

It is important to understand your workforce and customize your communications to meet diversity so you can deliver a clear message that all generations can hear.

 Call out important details such as:

  • Deadlines
  • Plan Changes
  • New Benefits
  • How to Enroll
  • Contribution Rates, including Increases
  • Calls to Action
  • Contact Information

Timing is Important

Properly timed open enrollment enhances employee satisfaction and engagement while facilitating efficient benefits management for the company. It is essential to provide employees with ample time to review, understand, and make informed decisions about their benefits options. Work backward from known deadlines that affect employees to begin the open enrollment process:

  • When do you want ID cards delivered?
  • When does the carrier need enrollment?
  • How long do we need to chase enrollments and reconcile statements?
  • Open enrollment needs to end by?
  • Open enrollment needs to begin with?
  • First communication should be?

Do Not Forget PPACA

The Patient Protection and Affordable Care Act, commonly known as ACA, has a new update this year explaining the solution to a family glitch that could be important to employees. For 2024, if the least expensive family coverage employee premium is unaffordable to the family, then the dependents may qualify for federal subsidies for coverage purchased through the state exchange. It is important to remember to count the hours of employees during the standard measurement period and test your plan for affordability under one of the safe harbors. Additionally, confirm the desired coverage is minimal in essentials and value and review the summary of benefits and coverage.

Now You Are Ready to Rock Open Enrollment Season

Communicating the enrollment timeline well in advance, offering clear and concise information about benefits options, and providing educational resources can empower employees to make well-informed decisions tailored to their needs. Encouraging early participation and fostering an environment where questions are welcomed can streamline the process and alleviate potential confusion. By heeding these open enrollment tips, organizations can ensure a smooth and successful enrollment period that leads to improved employee satisfaction, better utilization of benefits, and efficient benefits management overall. 

If you found this information helpful and are interested in how Shepherd Insurance can help with your insurance needs, contact us or visit our webinar series channel for additional recordings and upcoming events.