Choosing employee benefits shouldn’t feel like standing in the cereal aisle staring at 47 boxes that all promise to be the “right” choice. 

More options should help. More information should help. More time should definitely help. 

And yet, anyone who has spent 20 minutes comparing two nearly identical products knows what happens next: the longer you stare, the less certain you become. 

For many employees, open enrollment creates the same experience—except instead of debating granola, they’re making decisions that could affect their healthcare, finances, and families for the next year. 

According to the 2026 Selerix Employee Benefits Survey, 35% of employees regret the benefits choices they made during their last open enrollment. At the same time, 46% say they feel confident managing their benefits independently, while only 23% say they actually understand their benefits well. 

That’s a 23-point confidence gap. 

And it points to an important lesson for employers preparing for open enrollment: employees may not need more benefits information. They need better guidance for navigating it. 

During our recent webinar, Prepare for OE: One in Three Employees Regret Their Benefits Choices, Selerix VP of Partnerships Jasper Purvis explored what the latest employee research tells us about benefits decision-making—and what HR teams can realistically do about it. 

The answer isn’t to throw another 40-page benefits guide into the mix. It’s to make benefits easier to understand, more personal, and more useful before, during, and after enrollment. 

More Time Isn’t Necessarily the Answer. Better Guidance Is. 

When employees struggle with open enrollment, one logical response is to give them more time. 

Extend the enrollment window. Send the guide earlier. Give everyone another week to compare plans. 

But the 2026 Employee Benefits Survey uncovered a surprising pattern: employees who spent more than two hours making benefits decisions reported a 62% regret rate, compared with 23% among employees who spent less than 10 minutes. 

That’s not an argument for speed-running enrollment. Clicking through a medical plan election between meetings isn’t exactly the gold standard for thoughtful decision-making. 

Instead, the finding suggests that time spent isn’t necessarily understanding gained. 

Think about assembling furniture without instructions. Giving someone another two hours with the same mysterious pile of screws doesn’t necessarily improve the outcome. Giving them clear directions probably does. 

Benefits work the same way. 

Employees can spend hours comparing deductibles, premiums, copays, coinsurance, provider networks, HSAs, voluntary benefits, and coverage tiers without ever feeling certain they’ve made the right choice. Nearly half of employees in the survey reported navigating benefits decisions on their own, and only 28% felt guided step-by-step through enrollment. 

That’s the real opportunity for employers. Instead of asking, How much more information can we give employees?, ask a more useful question: 

How can we make the information they already have easier to understand and act on? 

That might mean explaining deductibles before enrollment begins. It might mean providing realistic cost scenarios instead of another chart full of insurance terminology. Or it could mean making personalized benefits decision support part of the enrollment experience so employees have guidance at the exact moment they’re choosing a plan. 

The goal isn’t to make employees benefits experts. It’s to help them become confident benefits consumers. 

Personalization Is the Lever More Employers Can Pull 

Outside of work, we’re surrounded by personalized experiences. 

Streaming services know what we might want to watch next. Shopping sites remember what we’ve browsed. Apps tailor notifications based on what we actually use. Even the coffee shop app knows better than to recommend an iced drink to someone who orders the same hot coffee every morning. 

Then open enrollment arrives, and thousands of employees can receive essentially the same message: 

It’s time to enroll. Here’s everything. Good luck. 

There’s a better way. 

The 2026 survey found a striking relationship between personalization and benefits satisfaction. Among employees who described their enrollment experience as extremely personalized, 76% reported very high satisfaction. Among employees who experienced no personalization, that figure dropped to 20%. 

That’s a 56-point difference—and it isn’t the result of adding another plan to the benefits package. It’s about improving the experience around the plans that already exist. 

Personalization doesn’t have to mean creating an entirely different campaign for every employee, either. Start by making communication more relevant. An employee enrolling in benefits for the first time may need a basic explanation of deductibles and coinsurance. Someone covering a family may benefit more from cost comparisons and examples of how different plans perform under common healthcare scenarios. An employee approaching retirement may have a completely different set of questions. 

The point isn’t to make assumptions based on someone’s age or circumstances. It’s to recognize that a workforce isn’t one audience. 

Modern employee benefits communication gives HR teams more opportunities to segment messages, reach employees through different channels, and provide information that feels relevant rather than generic. 

When a message feels like it was written for someone instead of simply sent to everyone, it has a much better chance of earning attention. 

Different Employees Bring Different Questions to Open Enrollment 

Personalization becomes especially important when you consider how benefits needs and familiarity can change throughout an employee’s career. 

The webinar highlighted three broad groups that illustrate the point well—not as rigid personas, but as a reminder that different employees can arrive at enrollment with very different levels of knowledge, experience, and confidence. 

Younger employees may need the benefits basics 

For employees ages 18–34, the research points to an education gap. Many are navigating employer-sponsored benefits independently for the first time, and some may have spent their first working years covered by a parent’s plan. 

Terms HR professionals encounter every day can still sound like a foreign language. 

Deductible. Coinsurance. Out-of-pocket maximum. HSA. FSA. In-network. 

If understanding those terms is necessary before someone can compare plans, don’t wait until they’re sitting inside the enrollment platform to explain them. 

Short videos, one-page explainers, quick definitions, mobile-friendly content, and simple examples can help build benefits literacy over time. Instead of handing employees the benefits equivalent of War and Peace, give them useful chapters they can actually absorb. 

Mid-career employees may need help weighing the tradeoffs 

Employees further into their careers may understand the terminology but face more complicated decisions. 

They may be covering a spouse or children, managing recurring prescriptions, anticipating a procedure, balancing household expenses, or trying to determine whether a lower-premium plan is really the less expensive option for their family. 

For this group, the question often isn’t What is a deductible? 

It’s What does this decision mean for us? 

This is where benefits decision support and realistic cost comparisons become especially valuable. Rather than simply showing employees two plan designs, help them understand the tradeoffs between premiums and potential out-of-pocket costs based on their individual needs. 

After all, “Plan A has a $2,000 deductible” is information. 

“Here’s how Plan A and Plan B could compare if your family expects regular prescriptions and several specialist visits” is guidance. 

Employees later in their careers may need help spotting what’s newly relevant 

Experienced employees create another challenge: familiarity can turn into autopilot. 

Someone who has enrolled in benefits for 20 or 30 years may already have a routine—open enrollment, find last year’s elections, make a few adjustments, submit. 

But benefits needs change. 

Options that didn’t seem important at 35 may deserve another look at 55. Employees approaching retirement may also have new questions about coverage transitions and how employer benefits interact with what’s ahead. 

The communication challenge here isn’t necessarily teaching Benefits 101. It’s helping employees recognize what deserves a fresh look this year. 

Across all three groups, the lesson is the same: don’t make employees dig through everything to find the few things that matter to them. 

Bring the relevant information closer. 

Take a look at our Benefits Communication Playbook for tips on communicating to the different generations.

Open Enrollment Communication Should Start Before Open Enrollment 

There’s a common timing problem in benefits communication: we wait until employees need to make a decision to begin explaining the decision. 

That’s a little like handing someone the owner’s manual when the check-engine light comes on. 

By the time enrollment opens, employees already have a task in front of them. They need to compare plans, consider costs, talk with family members, make elections, and meet a deadline. Trying to teach the entire benefits curriculum at the same time adds cognitive traffic to an already busy intersection. 

Instead, start earlier. 

As Jasper recommended in the webinar, employers can begin communicating 30 to 60 days before open enrollment, even if every plan detail or premium hasn’t been finalized yet. 

There’s plenty you can teach without announcing next year’s rates. 

Explain how a deductible works. Break down the relationship between premiums and out-of-pocket costs. Clarify the difference between an HSA and an FSA. Remind employees why provider networks matter. Show them where they’ll be able to find help. 

Then, as open enrollment gets closer and plan details are finalized, shift the communication toward what’s changing and what employees need to do. 

This approach also makes the actual enrollment period easier to digest. Instead of asking employees to learn the vocabulary, understand the plans, compare their options, and make a decision simultaneously, you’ve already given them some of the building blocks. 

Selerix’s Open Enrollment Guide follows the same broader philosophy: preparation is a process, not a two-week event. It breaks Open Enrollment tasks into a month-by-month easy process so you can stay ahead year-round. 

Make Benefits Communication Bite-Sized—Not Bland 

Simplifying benefits doesn’t mean stripping away useful information. 

It means respecting the fact that your employees have other things competing for their attention. 

A benefits email that requires eight uninterrupted minutes, a calculator, and a working knowledge of insurance terminology is probably not going to become everyone’s favorite afternoon read. 

So break it up. 

One message might cover the three things employees should know about their deductible. Another could explain why the lowest premium isn’t automatically the lowest-cost plan. A 60-second video could show employees where to find in-network care. A text message could remind them that enrollment closes Friday and link directly to the next step. 

The webinar emphasized using multiple touchpoints and multiple channels—email, text, mobile experiences, videos, benefit fairs, lunch-and-learns, Q&A sessions, and other formats that fit the workforce. 

This isn’t about bombarding employees from every direction. It’s about acknowledging that one communication channel will never work equally well for everyone. 

And repetition isn’t necessarily a bad thing. 

Employees are unlikely to remember a benefits concept because HR explained it once in August. Useful information needs opportunities to resurface. The trick is to repeat the lesson without simply resending the same giant email with REMINDER added to the subject line. 

The Best Benefits Education Doesn’t End When Enrollment Does 

One of the most important ideas from the webinar has very little to do with open enrollment itself: 

Employees don’t experience their benefits according to the benefits calendar. 

Babies aren’t considerate enough to arrive during OE. People get married in June. Someone needs an MRI in February. A prescription changes in April. A family member gets sick on an otherwise ordinary Tuesday. 

Those are the moments when benefits suddenly stop being an annual HR task and become very real. 

In the webinar, Jasper pointed to employees delaying or skipping care because of confusion about coverage, costs, or where to go. The survey data reinforces the broader problem: being enrolled in benefits doesn’t necessarily mean employees know how to navigate them. 

That’s why benefits education needs to continue throughout the year. 

A strong year-round strategy might include reminders about preventive care, explanations of underused benefits, guidance around qualifying life events, HSA or FSA deadlines, information about finding appropriate care, or simply reminders about where employees can go when they have questions. 

Life events are particularly valuable opportunities to make benefits communication personal. If an employee gets married, has a child, or experiences another qualifying event, that’s not just an administrative trigger. It’s a moment when benefits information is immediately relevant. 

That relevance matters. 

The 2026 Selerix Employee Benefits Survey describes a “navigation gap” between being enrolled in benefits and actually understanding, trusting, and using them. Year-round communication can help close that gap because education arrives when employees have a reason to care—not months before they need the information. 

Think less annual benefits firehose, more steady drip of useful information. 

Give Employees Real-Life Scenarios, Not Just Insurance Math 

Benefits professionals understand why premium, deductible, coinsurance, copay, and out-of-pocket maximum all belong in a plan comparison. 

Employees may see five numbers and wonder which one is going to hurt their wallet. 

Real-life scenarios can bridge that gap. 

Instead of explaining a plan exclusively through its components, demonstrate how those components might work together. 

What could the financial picture look like for an employee who expects only preventive care? What about someone who regularly sees a specialist? How might two plans compare for a family anticipating a pregnancy or a planned procedure? 

These examples don’t tell employees which plan to choose. They give employees a framework for evaluating the choice. 

And that’s exactly where personalized decision support can become useful. Selerix Decision Support is built into the benefits administration experience and uses guided questions to help employees evaluate plan options based on their needs. 

The distinction is important. 

A plan comparison says, Here are the numbers. 

Decision support helps answer, What might those numbers mean for me? 

When employees can connect benefits terminology to situations they recognize, the decision becomes less abstract—and confidence has a chance to replace guesswork. 

Start Small, Then Measure What Actually Works 

At this point, an HR leader could reasonably be thinking: Personalize communications, educate year-round, create multiple touchpoints, build scenarios, measure engagement…with what spare time? 

That’s fair. 

HR teams are already carrying plenty, and the answer isn’t to create an elaborate communication machine that becomes impossible to maintain by October. 

Start small. 

Pick one employee population or one recurring source of confusion. Send one or two targeted messages. Test a short educational video. Add one pre-enrollment communication. Introduce a simple feedback survey. 

Then measure it. 

Did employees open the message? Did they click through? Did more people use decision support? Did HR receive fewer questions about the topic? Did employees say the communication was useful? 

The webinar audience offered a revealing snapshot: 73% said most employees currently receive the same experience. That means “better personalization” doesn’t have to begin with a sophisticated 25-segment campaign. Moving from everyone gets everything to even a few thoughtfully targeted communications is progress. 

And if something doesn’t work, change it. 

As Jasper noted during the webinar, there’s no universal formula because every workforce is different. What matters is having enough feedback and reporting to recognize what’s working and stop repeating what isn’t. 

The Post-Enrollment Feedback Toolkit is one place to start. Employee feedback immediately after enrollment can help identify which communications connected, where confusion remained, and what employees wish they had known sooner. 

Because sending an ineffective email for the fourth year in a row doesn’t make it a tradition. It just makes it an ineffective email with seniority. 

Three Things You Can Do Before Your Next Open Enrollment 

You don’t need to reinvent your entire benefits strategy before enrollment begins. If resources are limited, focus on a few practical changes that can create a better employee experience. 

First, send one educational communication 30 to 60 days before enrollment. Pick something employees routinely struggle with and explain it clearly. Deductibles, networks, HSAs, or evaluating total plan cost are all good candidates. You can introduce useful concepts before employees have a deadline breathing down their necks. 

Second, turn at least one piece of benefits jargon into a real-life example. Don’t only define coinsurance. Show employees how it could affect the cost of care. Don’t only compare premiums. Explain why premium plus potential out-of-pocket spending creates a more complete financial picture. Give people something they can visualize. 

Third, make the path to help impossible to miss. Employees shouldn’t have to search old emails, hunt through an intranet, or send three messages to figure out where to ask a benefits question. Whether support comes from HR, a broker, a benefits counselor, educational resources, or decision support technology, make the next step obvious. 

Small improvements can compound. One clearer explanation becomes one fewer source of confusion. One targeted message becomes a template for another. One employee survey tells you where to focus next. 

You don’t have to boil the benefits ocean. 

The Goal Isn’t Enrollment. It’s Confidence. 

Open enrollment has an obvious finish line: elections submitted, enrollment closed, files sent. 

But completion alone doesn’t tell us whether the experience worked. 

An employee can successfully click Submit and still wonder whether they chose the right plan. They can have excellent coverage and still delay care because they don’t understand how to use it. They can feel confident about their benefits while lacking the understanding necessary to navigate them when something actually happens. 

That’s the gap employers have an opportunity to close. 

The latest Selerix research suggests the answer isn’t simply more plans, more PDFs, more emails, or more days on the enrollment calendar. It’s better navigation: relevant communication, personalized guidance, practical decision support, and education that continues after enrollment ends. 

The goal isn’t to turn every employee into an insurance expert. 

It’s to help employees understand enough to say, “I know why I made this choice, and I know what to do when I need to use it.” 

That’s a much better measure of open enrollment success. 

And hopefully, it means far fewer employees looking back at their elections six months later and wishing they’d chosen differently. 

Want to Dig Deeper? 

Watch the full Selerix webinar, Prepare for OE: One in Three Employees Regret Their Benefits Choices, for more findings from the 2026 Selerix Employee Benefits Survey and practical strategies HR teams can use to improve benefits communication, personalization, and decision support ahead of open enrollment. 

You can also explore the 2026 Selerix Employee Benefits Survey for a deeper look at the confidence and navigation gaps shaping the employee benefits experience.