Introduction: Why Open Enrollment Feels So Overwhelming

For many HR leaders, open enrollment season is the busiest—and most stressful—time of the year. Employees are expected to sort through complex benefit options, review plan changes, and make decisions that affect their financial and personal wellbeing for the entire year. Meanwhile, HR teams juggle policy updates, benefits vendor coordination, and an endless stream of employee questions.

The real challenge is not the benefits themselves. It’s communication.

According to the International Foundation of Employee Benefit Plans (IFEBP), 80% of employers report that employees don’t read open enrollment materials thoroughly. The result is predictable: missed deadlines, uninformed decisions, and confusion that creates more work for HR.

In this blog, we’ll explore the most common mistakes HR makes with open enrollment communication—and how to fix them. You’ll also get a ready-to-use 3-email template series you can copy and paste this week to improve clarity, engagement, and enrollment rates.

Mistake 1: Sending Too Much Information at Once

Most HR teams feel pressure to give employees every single detail upfront. The result? A 20-page PDF or a long intranet post that no one actually reads.

This approach creates information overload. Employees skim, get overwhelmed, or put it off altogether. By the time they return to the materials, deadlines are looming and HR is fielding repetitive questions.

How to Fix It

  • Break content into smaller parts. Instead of one long message, send a series of shorter, focused emails.
  • Highlight key actions. Emphasize what employees need to do rather than burying them in definitions.
  • Layer resources. Provide a one-page summary, then link to detailed plan guides for those who want them.

Example: One tech company cut their open enrollment emails from 1,200 words to 300 words with links to FAQs. Result: a 40% increase in portal logins during week one of open enrollment.

Mistake 2: Using Complex or Technical Language

Benefits terminology is notoriously confusing. Terms like deductible, coinsurance, HSA, PPO, and FSA make employees feel like they need a dictionary before they can make a decision. This confusion leads to inaction, frustration, or poor plan choices.

How to Fix It

  • Use plain language. Translate “deductible” into “the amount you pay before insurance starts helping.”
  • Provide real-life examples. For instance: “If you visit the doctor and your deductible is $500, you’ll pay out-of-pocket until that amount is met.”
  • Add visuals. Charts, infographics, and simple icons improve comprehension.

Example: A retail company replaced technical terms with “before insurance helps” and “your share of the bill.” Employee surveys showed a 25% improvement in confidence about plan selection.

Mistake 3: Waiting Too Long to Communicate

Many HR teams wait until the last week—or even the last few days—of enrollment to send reminder emails. By then, employees feel rushed, overwhelmed, or simply miss the deadline.

How to Fix It

  • Start early. Announce enrollment the day it opens, with clear dates and instructions.
  • Send mid-cycle nudges. A reminder halfway through ensures employees don’t forget.
  • Close with urgency. A “final countdown” message boosts last-minute participation.

Stat: A LIMRA survey found that employees who received at least three reminders were twice as likely to complete enrollment on time compared to those who only received one.

Mistake 4: Failing to Personalize Messages

A 25-year-old employee just starting their career does not need the same benefits information as a 50-year-old parent planning for retirement. Yet most HR communication is one-size-fits-all.

The result? Employees tune out because they don’t see the relevance.

How to Fix It

  • Segment by life stage. Send tailored examples: “Parents may want to compare childcare benefits,” or “Young employees may benefit from the HSA option.”
  • Use names. Personalization, even as simple as addressing employees by first name, increases email open rates.
  • Offer targeted FAQs. For example, separate FAQs for early-career employees, families, and near-retirees.

Example: A healthcare organization created three email tracks: one for singles, one for parents, and one for employees over 50. The result? Enrollment satisfaction scores jumped 30%.

Mistake 5: Forgetting Reminders

Even employees with the best intentions get busy. Without reminders, forms remain incomplete. HR then spends the last week chasing employees one by one.

How to Fix It

  • Build a reminder cadence. Use three touchpoints: kickoff, mid-cycle, and final countdown.
  • Mix channels. Send reminders via email, intranet banners, Slack/Teams posts, and even text messages.
  • Make deadlines visible. Use bold text, banners, or countdown clocks to make urgency impossible to miss.

Stat: A SHRM study showed that adding reminders increased enrollment completion by 22%, reducing last-minute admin work for HR.

The Fix: A 3-Email Open Enrollment Series

Here’s a ready-to-use email series that solves these mistakes.

Email 1: Kickoff Announcement

Subject line: Open Enrollment Starts Today—Here’s What You Need to Know

Hi [First Name],

Open Enrollment is officially open. This is your chance to review your benefits, compare options, and make updates for the coming year.

What you need to know:

  • Enrollment window: [Start Date] – [End Date]
  • What you’ll need: [Dependent info, ID card, login credentials]
  • Where to enroll: [Link to portal]

Start early so you have plenty of time for questions.

[Start Enrollment]

— [Your HR Team]

Email 2: Midpoint Reminder with FAQs

Subject line: Reminder: Open Enrollment Ends in [X] Days

Hi [First Name],

We’re halfway through the enrollment window. If you haven’t enrolled yet, now is the time.

Common questions we’ve heard:

  • What happens if I don’t enroll? [Answer]
  • Where do I find plan comparisons? [Answer/link]
  • Who can I contact with questions? [Answer]

The deadline is [End Date]. Please complete your enrollment before then.

[Complete Enrollment]

— [Your HR Team]

Email 3: Final Countdown

Subject line: Last Chance—Open Enrollment Ends Tomorrow

Hi [First Name],

This is your final reminder: Open Enrollment ends tomorrow, [End Date]. After this deadline, you may not be able to make changes until next year.

Act now to:

  • Review your current benefits
  • Explore new options
  • Confirm your elections for 2024

It only takes 10 minutes.

[Finish Enrollment Now]

— [Your HR Team]

Why This Approach Works

This three-email series fixes the top five mistakes:

  • It avoids information overload by splitting messages.
  • It uses plain, accessible language.
  • It spaces communication across the entire enrollment period.
  • It allows for personalization and FAQs.
  • It builds in reminders that drive action.

The result is less stress for HR and more clarity for employees.

Beyond Email: Additional Engagement Tactics

While email is the backbone of open enrollment communication, it shouldn’t be the only channel. To maximize engagement:

  • Send text message nudges. A quick reminder with a portal link can be highly effective.
  • Post in Slack or Teams. Share countdown graphics and answer questions in real time.
  • Create short videos. Have leaders explain why benefits matter in under two minutes.
  • Provide manager talking points. Equip managers to remind employees during team meetings.
  • Use printed signage. Posters in break rooms or QR codes on bulletin boards can catch attention.

Multi-channel communication ensures your message reaches employees no matter how they prefer to engage.

Measuring Communication Success

How do you know if your new approach is working? Track:

  • Open rates: Did employees read the emails?
  • Click-through rates: Did they click the enrollment link?
  • Completion rates: How many finished enrollment before the deadline?
  • Question volume: Did HR receive fewer last-minute inquiries?

These metrics give you a clear picture of what’s working and what to refine for next year.

How Woliba Helps HR Leaders

Even with templates, manual communication is time-consuming. Woliba helps HR teams automate open enrollment communication through:

  • Automated reminders via email, chat, or mobile
  • Engagement dashboards to track participation
  • Pre-built templates for benefits campaigns
  • Personalized nudges based on employee role or demographics

Instead of manually sending updates, HR can set campaigns once and let Woliba keep employees informed—freeing time for higher-value work.

Conclusion: From Chaos to Clarity

Open enrollment will always be complex. But most of the stress comes from communication mistakes: overwhelming employees with too much information, using confusing language, waiting too long, failing to personalize, or forgetting reminders.

By avoiding these pitfalls and using a structured 3-email series, HR leaders can dramatically improve participation, reduce confusion, and cut down on last-minute admin work.

Clear communication is not just good practice—it’s the difference between a chaotic season and a successful one.

To learn how Woliba helps HR teams simplify communication, automate reminders, and keep employees engaged, visit woliba.io.