How medium to large employers can simplify health insurance season—and actually enjoy it
Open enrollment season has a reputation. For many medium to large employers, it’s marked by inbox overload, employee confusion, last-minute scrambles, and a lot of crossed fingers. At Stolly Insurance, we hear it every year: open enrollment feels more like something to survivethan succeed at.
The good news? It doesn’t have to be that way.
Here are the most common pain points we see—and practical ways to make open enrollment smoother, clearer, and far less stressful for everyone involved.
Common Open Enrollment Pain Points
- Information overload (and underload at the same time)
Employees receive dense plan documents filled with jargon but still don’t get answers to the questions they care about most:
What’s changing? How much will it cost me? Which plan makes sense for my family? - Low employee engagement
When open enrollment feels confusing or rushed, employees disengage. Many default to last year’s plan or make choices they later regret—leading to frustration and more HR questions. - Administrative bottlenecks
HR teams juggle deadlines, carrier requirements, compliance concerns, and countless employee questions—all at once. One missed step can create issues long after enrollment closes. - Change fatigue
Even positive changes can create resistance if they aren’t communicated clearly and early. Surprises during open enrollment are rarely welcome ones.
- Start communication earlier than you think you need to
Open enrollment shouldn’t start the day enrollment opens. Early reminders about timelines, expectations, and upcoming changes help employees feel prepared instead of panicked. - Simplify the message
Clear, plain-English summaries go a long way. Focus on:- What’s changing (and what’s not)
- Who is impacted
- What actions employees need to take and by when
Detailed documents still matter—but clarity should come first.
- Offer decision support, not just documents
Employees want guidance, not PDFs. Plan comparisons, cost examples, and FAQs help employees make confident decisions and reduce repeat questions to HR. - Use multiple communication channels
One email isn’t enough. Reinforce key messages through:- Emails
- Short videos or webinars
- Intranet posts
- Live or recorded Q&A sessions
Thoughtful repetition builds understanding and confidence.
- Make enrollment and administration easier for HR
That’s where technology matters. Stolly provides Employee Navigator at no cost to our clients—a powerful platform that helps HR teams:- Manage enrollments
- Track employee elections
- Streamline onboarding and compliance
- Reduce manual work and errors
It’s a tool designed to make open enrollment easier for HR and clearer for employees.
- Make help easy to access
Employees should always know where to go with questions—whether that’s HR, the enrollment platform, or their Stolly advisor.
At Stolly Insurance, we work alongside HR and leadership teams to take the chaos out of open enrollment by:
- Designing clear, employee-friendly communication strategies
- Implementing tools like Employee Navigator to streamline the process
- Providing education and decision support employees actually use
- Reducing administrative burden and last-minute fire drills
Our goal is simple: make open enrollment easier for your team and more valuable for your employees.
If you’re ready to turn open enrollment from a yearly headache into a well-run, confidence-building experience, we’re here to help. Let’s make this the year open enrollment finally works for you—not against you.
Disclaimer: This article was drafted with the assistance of AI and reviewed for accuracy and clarity before publication.