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How can employers avoid annual enrollment pitfalls and drive success this season? 

Annual Enrollment, aka AE: The one time a year when employees get the opportunity to choose and update their benefits for the upcoming year. For many HR professionals, this period is the culmination of months of preparation—the Super Bowl of the HR industry. 

While every benefits administration professional hopes for ideal AE outcomes—employees enrolling on deadline, engaging with materials, and making appropriate and cost-effective elections—it takes a deliberate communication strategy (along with a  little luck) to ensure success, especially when dealing with a hybrid workforce, as many employers are post-pandemic. 

Will the upcoming Annual Enrollment season uphold the status quo? 

Our 2022 Benefits Insights Report reveals that 82% of employees are confused about their benefits, a statistic that has held for the last three years. 

With so many employees still confused about their benefits, how can employers get ahead of the AE curve? And implement strategies to combat the confusion employees are experiencing? 

It starts with humanizing the benefits experience and practicing empathy throughout enrollment. Over 80% of employees say that being treated like a person, not a number, is essential for keeping and retaining their attention. 

Ironically, personalization starts with paying attention to the available numbers. Leveraging data to increase custom communications is a way to show empathy and help employees to easily choose relevant care options. 

What employee communication best practices can HR teams use in AE 2023? 

Every organization is different, so there’s no one path to AE success, but the more prepared an organization is, the better. As HR and executives discuss upcoming plan changes, timely population needs, and how to see greater employee engagement and participation in AE, here are five ways to drive success: 

  1. Personalize your benefits outreach.  
  2. Track the data before, during, and after enrollment.  
  3. Leverage traditional communications in new ways throughout your organization.  
  4. Empower your HR teams to be your health care marketers.  
  5. Lean on employee feedback. 

Watch our panel session, “Oh, the Places You’ll Enroll: Effective AE Strategies for a Hybrid Workforce. 


Practicing empathy during Annual Enrollment is more important than employers think. 

These tactics perform best when implemented alongside a supportive organizational culture.  

Empathy perceptions are nearing an all-time low, with only 69% of employees saying their organizations are empathetic. This statistic should be enough to concern any organization that wishes to run an effective Annual Enrollment. A lack of empathy during AE can lead to confusion surrounding the “why” of plan changes, including cost increases or other shifts in benefits access.  

Since Annual Enrollment is the launchpad for year-round employee benefits engagement, it’s essential to practice empathy during AE and the entire year.   

But what’s attributing to the growing empathy gap? The answer lies in shifting executive priorities back to the bottom line while many employees continue to struggle with the lingering effects of the pandemic. 

As the world continues to normalize, it’s easy to forget that many employees are still dealing with ongoing mental health concerns, financial uncertainty, and health scares. Practicing empathy, especially during annual enrollment, can help ease tension and improve employee engagement. 

Want to learn more about achieving year-long success by conquering the empathy gap? Register for our Aug. 2 webinar, “Eavesdropping on the C-Suite: How executives are responding to the empathy gap.” 

View all Posts by Madicyn Maines