Let’s be honest—open enrollment meetings aren’t known for drawing standing-room-only crowds. Attendance is often low, engagement is spotty, and even when employees show up, retention of the information tends to be minimal. Meanwhile, the person who actually makes the benefits decisions—the spouse or partner at home—is often nowhere near the meeting.

In response, more and more companies are scrapping benefits meetings altogether in favor of emails, PDFs, and self-service portals. But this shift might be a mistake.

With rising healthcare costs, evolving plan options, and increasing employee demand for personalized benefits, employers need more, not less, communication. The key is not to eliminate open enrollment meetings—but to spice them up, make them more accessible, and ensure they’re worth employees’ time and attention.

In this blog, we’ll explore how HR and finance professionals can breathe new life into open enrollment meetings, boost attendance, and make them a valuable part of your total rewards strategy.

The Problem: Why Traditional Open Enrollment Meetings Fail

Before we explore solutions, let’s understand why traditional meetings often fall flat:

• Dry content: Insurance terminology, contribution tiers, and voluntary benefits aren’t exactly thrilling topics.
• One-way delivery: Presenters talk at employees instead of engaging with them.
• Timing issues: Meetings often occur during peak work hours, are rushed, or clash with production schedules.
• Information overload: Employees are bombarded with too many changes in a short time.
• Missing decision-makers: Spouses and partners—who often have final say—aren’t present.
• No follow-up: Employees forget 90% of what they hear if it isn’t reinforced through other channels.

Why Getting Rid of Meetings Isn’t the Answer

It’s tempting to replace live meetings with digital content. After all, self-service platforms and on-demand videos are scalable, measurable, and flexible.

But here’s the catch: benefits are one of the most complex and emotionally driven components of compensation. Employees need time, guidance, and reassurance. When done well, open enrollment meetings:

• Improve benefits literacy
• Increase voluntary benefit participation
• Reduce incorrect elections and rework
• Build trust in HR and leadership
• Allow for live Q&A and clarification

The challenge isn’t the meeting itself—it’s the format and delivery.

How to Make Open Enrollment Meetings More Engaging

Here are proven strategies to turn dull meetings into dynamic, informative, and even enjoyable experiences.

1. Make Them Optional, But Valuable

Forced attendance leads to resentment. Instead, create multiple session options at various times (and offer a virtual option). Then make the value of attending crystal clear:

• Live Q&A with a benefits expert
• Early access to giveaways or raffles
• Help completing the election process
• Real examples of how to save money

Let them know: This is not the same old meeting. This is your chance to get clarity, save money, and ask real questions.

2. Invite the Household Decision-Maker

Remember: many employees aren’t the final decision-maker on benefits. Spouses and partners often drive these choices.

Solution: Offer evening or weekend virtual sessions and explicitly encourage employees to invite their partner.

“Choosing benefits is a family decision—invite your spouse to join this session so you can make the best choice together.”

Bonus: Record the session and provide a shareable link.

3. Add a Human Touch

Open with a story or testimonial—an employee who saved thousands with an HSA, or someone who used accident insurance to cover an unexpected injury.

Real stories humanize the benefits and show practical value.

Consider co-hosting with someone from payroll or an actual employee who’s navigated the benefits process. These stories stick more than spreadsheets.

4. Gamify the Experience

Gamification doesn’t need to be cheesy. Small incentives go a long way:

• Raffles for gift cards
• Trivia quizzes with health-related prizes
• “Find the Fact” scavenger hunts during the session

Use tools like Kahoot! or Slido to run polls and live Q&A. It makes the session feel more like a workshop and less like a lecture.

5. Break Down Complex Topics Visually

Replace dense bullet points with:

• Infographics comparing plans side-by-side
• Animations explaining how deductibles work
• Decision trees to guide plan selection
• Personalized “benefit journey” scenarios

Visuals work. Employees understand faster, remember longer, and are more likely to take action.

6. Create Mini-Sessions by Topic

Don’t try to cram everything into one hour. Break your content into digestible segments:

• “Understanding the New Medical Plan in 15 Minutes”
• “How to Use Your FSA & HSA Wisely”
• “Voluntary Benefits: Worth It or Not?”

Host these as quick lunchtime “benefits bites” or as part of a rolling series.

7. Leverage Vendor Partners

Don’t carry the full load alone. Your insurance carriers, brokers, and TPAs are often willing to:

• Co-host meetings
• Provide speakers
• Share marketing assets
• Offer 1-on-1 enrollment support

Make sure vendor materials match your tone, branding, and plan specifics. Use them strategically—not as a replacement for internal trust-building.

8. Follow Up with Personalization

The meeting is just one touchpoint. Reinforce it with:

• Targeted follow-up emails (e.g., “Still undecided? Here’s a plan comparison tool.”)
• Text message reminders about deadlines
• Access to recordings and slide decks
• Quick polls to ask: “Do you feel confident about your benefits choices?”

Use analytics to measure attendance, questions asked, and benefit elections.

What Not to Do

Avoid these common mistakes:

• Using insurance jargon without definitions
• Delivering a monotone, slide-heavy monologue
• Assuming everyone learns the same way
• Ignoring cultural or language differences
• Treating it as a compliance checkbox, not a people process

Your benefits package is one of your biggest investments. Present it accordingly.

The ROI of a Better Meeting

Well-run benefits meetings yield measurable returns:

• Higher enrollment in voluntary benefits like HSAs, critical illness, or legal services
• Fewer mistakes during enrollment, which reduces administrative rework
• Better appreciation of total compensation, which improves retention
• Higher benefits literacy, which boosts utilization and satisfaction

And most importantly, you get fewer panicked emails from employees asking, “What’s an HSA again?” on the final day of enrollment.

Final Thoughts: Don’t Kill the Meeting—Reinvent It

The instinct to abandon open enrollment meetings is understandable—but short-sighted. With rising costs and complex options, employees need help more than ever. The key is to reimagine your meetings to fit today’s hybrid, distracted, digital-first workforce.

Investing in just a few enhancements—better timing, clearer visuals, spouse participation, and human storytelling—can transform enrollment meetings from a burden into a benefit. Because when people understand their benefits, they make smarter choices. And that’s a win for everyone—employees, HR, and the company’s bottom line.