Open enrollment has a lot riding on it. Employees need to review their options, understand what changed, compare plans, think about what they might need in the year ahead, and make decisions before the deadline. HR, meanwhile, is managing eligibility, answering questions, fixing issues, sending reminders, and trying to keep the entire process moving. 

And somewhere along the way, open enrollment picked up another job: teaching employees how their benefits work in the first place. That’s a lot to ask of a two-week window, especially because choosing benefits isn’t just another task on an employee’s to-do list. These decisions have to work in their actual lives. 

An employee with a toddler may be thinking about pediatrician visits, prescriptions, and the inevitable daycare germs. Someone planning to grow their family may be looking at coverage through an entirely different lens. Another employee may be managing ongoing care, supporting a spouse, thinking more seriously about retirement, or simply trying to understand health insurance for the first time. The same benefits menu can mean something completely different to every person looking at it. 

When employees hear little about their benefits throughout the rest of the year, open enrollment becomes responsible for everything at once. Employees aren’t just choosing benefits. They’re learning the terminology, figuring out what applies to them, comparing options, and trying to connect all of that information to the lives they expect to live next year. No wonder it can feel overwhelming. 

Open enrollment shouldn’t be the beginning of benefits education. It should be the moment that education pays off. 

Employees Are Taking the Test While Learning the Material 

Think about everything an employee might be trying to figure out during open enrollment. What’s a deductible again? How is that different from an out-of-pocket maximum? Should I contribute to an HSA or FSA? Is my doctor still in network? What changed this year? Do I need supplemental coverage? How much is actually coming out of my paycheck? 

Deductibles. Copays. Coinsurance. Out-of-pocket maximums. HSAs. FSAs. Networks. Coverage tiers. For HR and benefits professionals, these may be everyday terms. For employees who haven’t thought about them since the last enrollment period, benefits can start to feel like a different language. Selerix’s guidance on reducing benefits regret makes the same point: terminology that feels routine to HR can still create a major education gap for employees trying to navigate their options. Benefits Choice Regret Is Real: Here’s How HR Can Reduce It Before Open Enrollment 

And underneath all those insurance terms are much more personal questions: Will this work for my family? What if something happens this year? Can I afford the care I expect to need? Am I choosing the right thing? 

Benefits decisions aren’t purely administrative. They can be financial, practical, and emotional all at once. Employees are choosing coverage they may depend on during some of the most important—and sometimes most stressful—moments in their lives. Then, after sorting through all of that, they still have to choose. 

It’s the benefits equivalent of learning the material while taking the final exam—and the answers aren’t the same for everyone. 

According to the 2026 Selerix Employee Benefits Survey, 35% of employees regret their benefits choices. The research also found a 23-point gap between employees who feel confident managing their benefits and those who actually understand them well. 

That’s bigger than an enrollment problem. An employee can successfully submit their elections and still walk away unsure whether the benefits they chose will actually support them when they need them. 

Enrollment completed? Yes. Benefits understood? Maybe not. 

“We Sent It” Doesn’t Mean “They Learned It” 

There’s no shortage of benefits information. The benefits guide went out. The portal has plan details. The reminder emails were sent. The Summary Plan Description is available. Maybe there was even an enrollment meeting or webinar. On paper, everything was communicated. 

But communication doesn’t guarantee comprehension. Just because information was delivered doesn’t mean it was absorbed, retained, or understood. And simply making more information available places the burden on employees to figure out what matters, what it means, and how it applies to them. 

Benefits education has to do more. It has to help employees connect the information they’re receiving to the decisions they’ll eventually need to make, and that becomes especially important because every employee brings a different set of circumstances to those decisions. 

A 25-year-old choosing coverage for the first time may need help understanding the fundamentals. A parent with young children may be focused on different plan features than an employee whose children have left home. Someone managing an ongoing condition may be looking closely at prescriptions and provider networks. Someone approaching retirement may suddenly have questions they’ve never needed answered before. 

They don’t necessarily need completely different benefits information. They need help finding and understanding the parts that matter to them. 

That’s one of the central ideas behind The Connected HR Playbook. HR can meet every deadline, check every eligibility box, and make every required document available while employees still feel confused about their coverage or unsure where to go for help.  

And good benefits communication can help close that gap. As Selerix explores in The Three Questions Every Benefits Message Must Answer, employees need to quickly understand whether a message applies to them, what they need to do, and why it matters. 

The goal isn’t to communicate everything. It’s to help employees understand what matters enough to act on it. 

Don’t Wait Until There’s a Decision to Make 

If open enrollment is the moment employees need to choose what’s right for themselves and their families, it shouldn’t also be the first time they’re introduced to the concepts behind those decisions. 

Because there isn’t one “right” benefits choice for every employee. One person may be prioritizing lower premiums. Another may be thinking about regular specialist visits or prescriptions. A parent may be weighing coverage for an entire family. Someone planning a major life change may be looking at benefits they barely considered the year before. 

Different goals. Different health needs. Different dependents. Different financial circumstances. Different lives require different considerations. 

When employees are asked to sort through all of those considerations while simultaneously learning what their benefits mean, the pressure only grows. Education gives employees something valuable before enrollment arrives: time to understand before they have to decide. 

Employees don’t need next year’s final rates to learn how deductibles work. They don’t need the enrollment portal open to understand the difference between an HSA and an FSA. They don’t need a deadline three days away before they start thinking about which benefits may matter most to them or their families. 

HR can start with the fundamentals and build from there. Selerix recommends beginning education before enrollment even when every plan detail isn’t finalized, then getting more specific about changes, costs, deadlines, and decisions as the enrollment window approaches. Benefits Choice Regret Is Real: Here’s How HR Can Reduce It Before Open Enrollment 

Instead of asking employees to go from “What does this mean?” → “Choose now,” give them room to move through Learn → Understand → Consider → Compare → Decide. 

By the time open enrollment arrives, employees aren’t starting from zero. They’re applying what they’ve learned to the circumstances, priorities, and people that matter to them. 

Year-Round Doesn’t Mean All. Year. Long. 

At this point, an HR professional could reasonably be thinking: Great. So now I’m supposed to talk about benefits every week? 

Nope. 

Year-round benefits education isn’t about filling employee inboxes with more benefits messages. It’s about strategic communication: considering when a message should be sent, who actually needs to receive it, and what that employee needs to understand at that moment. 

That could mean an FSA balance reminder to employees who actually have an FSA while there’s still time to use those dollars. A wellness benefit refresher when it’s particularly relevant. Clear benefits basics for employees approaching eligibility. Or information tied to a life event when an employee suddenly has decisions to make. 

The point isn’t to keep benefits constantly top of mind. It’s to make sure useful information shows up when employees are more likely to need, understand, and act on it. 

Selerix’s year-round benefits engagement guidance similarly emphasizes keeping benefits relevant beyond enrollment rather than treating communication as a once-a-year event. 

Better-timed communication, delivered to the employees who need to hear it most. That’s very different from simply sending more. 

Employees Don’t Live by the HR Calendar 

Strategic communication also means recognizing that the moments that matter to employees don’t always line up neatly with the benefits calendar. 

Because HR has a benefits calendar. Employees have lives. 

HR thinks about eligibility periods, enrollment windows, renewals, reporting requirements, and compliance deadlines. Employees think about benefits when something makes them matter. 

A new employee is trying to understand coverage while learning a new job. A parent may suddenly need to know exactly what their plan covers when their child gets sick. Someone getting married might need to understand how and when coverage can change. Another employee might go months without thinking about a particular benefit until the exact moment they need to use it. 

Those moments don’t conveniently wait for open enrollment. That’s why The Connected HR Playbook encourages HR teams to look beyond the administrative calendar and follow the employee experience instead.  

And the data suggests relevance matters. The Playbook reports that 51% of employees say content that feels personal to their situation is what’s most likely to prompt them to act. Nearly one in three employees who ignored an open enrollment message said it didn’t feel relevant to them.  

The 2026 Selerix Employee Benefits Survey reinforces that challenge from another angle: only 20% of employees say benefits communications consistently reach them when they’re ready to act. 

So instead of starting with “What benefits message are we supposed to send this month?” try asking, “Who needs to hear from us right now—and what would actually help them?” 

Sometimes that’s education. Sometimes it’s a reminder. Sometimes it’s a deadline. Sometimes it’s reassurance that they’re looking in the right place. 

Not more communication. More relevant communication. 

Better Prepared Employees Can Mean Less Reactive HR 

There’s another person who benefits when employees receive relevant education throughout the year: HR. 

When employees are confused, HR gets the question. When a communication doesn’t make sense, HR explains it. When someone isn’t sure what action to take, HR helps them navigate it. And when an employee realizes after enrollment that they misunderstood something, that question usually finds its way back to HR, too. 

The Connected HR Playbook describes these as some of the people costs HR absorbs when benefits administration, compliance, and communication operate separately.  

Better education won’t eliminate employee questions—and it shouldn’t. Benefits are personal, and sometimes employees need another human being to help them understand how a complicated set of options intersects with a complicated life. 

But there’s a difference between helping an employee navigate a unique situation and answering the same foundational question for the 15th time during open enrollment. Proactive education can help address some of those questions before they become urgent, giving HR more room for the conversations where human support really matters. 

Make Open Enrollment the Finish Line, Not the Starting Line 

Now imagine an employee entering open enrollment with a foundation already in place. They understand the benefits they currently have. They know the basic terminology. They’ve received useful, relevant information throughout the year. And they’ve had opportunities to understand their benefits before those benefits became an urgent decision. 

Most importantly, they’ve had time to think: What changed in my life this year? What might change next year? Which benefits did I actually use? Where did I spend more than expected? What support might I or my family need? 

Those are the questions open enrollment should give employees room to answer. 

Instead of “What does all of this mean?”, employees can focus on What’s changing? What matters for my life right now? Which option makes sense for me? What do I need to do next? 

That’s what open enrollment is better suited to do: help employees put what they’ve learned into action. And it’s at the heart of the connected approach outlined in The Connected HR Playbook: benefits administration, compliance, and employee communication working together as one continuous experience rather than separate events employees have to piece together themselves.  

Two Weeks Can’t Do Twelve Months of Work 

Open enrollment matters. But it can’t carry an entire benefits education strategy by itself. 

Because benefits aren’t really about deductibles, eligibility dates, enrollment portals, or plan documents. They’re about what happens when an employee actually needs them. 

They’re about taking a child to the doctor, filling a prescription, planning for a growing family, managing an ongoing health need, protecting a paycheck, or preparing for the future. Those are personal decisions, and the goal isn’t to turn employees into benefits experts. It’s to give them enough education, context, and support to make informed choices for the lives they’re actually living. 

That means moving education beyond the enrollment window and into the moments when it can actually help—before a decision, around a life event, after enrollment, or simply when a benefit becomes relevant. 

Stop asking two weeks of open enrollment to do twelve months of work. 

When benefits education becomes a relevant, year-round conversation, employees can arrive at enrollment better prepared to make choices for themselves and their families. And HR can spend less of the season trying to make up for everything employees didn’t have an opportunity to learn before it started. 

Want to build a more connected benefits experience? Explore The Connected HR Playbook for practical ways to bring benefits administration, compliance, and employee communication together throughout the employee journey.