Annual enrollment. It’s only two words. But these are words with the power to make employees’ eyes glaze over and send HR teams into overdrive. In theory, annual enrollment is when employees confidently choose the benefits that fit their needs. But in practice, the process often just confuses, frustrates, and overwhelms everyone involved.

In the end, trust between employees and HR often takes a hit. And that goes double when enrollment communication doesn’t deliver the clarity and support people need. But it can be different.

When done right, annual enrollment is about more than just selecting benefits. It’s a chance to reaffirm connections, empower decision-making, and show employees that their organization truly has their back.

Why annual enrollment often misses the mark

You know it, and so do we: HR teams put an incredible amount of time and effort into their enrollment strategies. But nonetheless, many employees see things differently. According to one survey, while 74% of HR leaders believe their enrollment strategy is effective, only 37% of employees agree.

That’s a real disconnect.

What those numbers show is that employees are struggling quietly while HR operates under the assumption that everything’s fine. According to another recent survey, 53% of employees regretted the choices they made during their last open enrollment period.

Employee pain points

The top three reasons employees regret their annual enrollment choices:

• 25% forgot to adjust their benefits to match lifestyle changes.
• 20% failed to make their benefits selections and changes by the deadline.
• 19% didn’t understand their options or the benefits they selected.

They found that employees don’t spend much time — an average of 30 to 60 minutes — selecting their benefits. And SHRM says 51% of Gen Z and Millennials have chosen a health plan aimlessly due to confusion. One in four members of Gen X were just as confused by their benefits.

All this points back to an internal communications issue around enrollment. And when that communication gap isn’t addressed, employees stew. They feel unsupported and confused, and HR’s efforts don’t pay off. There are follow-up questions, compliance headaches, and missed opportunities to strengthen employee engagement.

The business risks of poor employee communication

A recent Harris Poll report on the state of business communication laid out the costs of ineffective employee communication. The costs reach beyond enrollment, seeping into workplace culture:

• 51% of knowledge workers report increased stress due to poor communication.
• 41% say it decreases their productivity.
• 35% feel it reduces job satisfaction.

The good news is, on the flip side, almost two-thirds of business leaders say effective employee communication boosts productivity.

Better productivity, less stress, better job satisfaction, and the trust that comes with that is possible. All we need to do is change how we communicate with employees. Easy, right? With the steps below (and maybe the right partner), it can be.

Building trust through better enrollment communication

While having good looking enrollment materials is nice, trust isn’t built just because the brochure is glossy, or the email is flashy. It’s built by showing employees you understand their needs. It’s built by speaking their language and making the process as easy and accessible as possible. Here’s how to make that happen.

1. Know your workforce needs and preferences

Not all employees approach enrollment the same way, and that’s okay. What’s not okay is continuing to send out the same one-size-fits-all communications that leave workers fending for themselves.

Demographics matter. A younger hire at their first or second job may need more handholding than a seasoned professional whose career spans decades. But it’s not just about age or career stage. How employees take in information and act on it can vary based on their work environment and personal responsibilities, too. Recognizing these nuances is key to designing communication strategies that truly stick.

Tailor your messaging to your audience. For deskless workers, consider text reminders with links to benefits summaries. For employees who do their best thinking after work, offer a public benefits microsite they can explore with their families. Meeting employees where they’re at helps them feel supported, not left to figure things out alone.

2. Cut the jargon and speak like a human

Another way to help employees feel supported is to use plain language. Insurance terms like “deductibles” and “co-insurance” might as well be a foreign language to many employees. It’s time to simplify:

• Instead of “This plan includes a co-insurance requirement of 20%,” say, “This plan covers 80% of your medical costs after you pay your deductible.”
• Break dense information into digestible chunks with bullets or quick explainer videos

Accessible language builds trust. When employees actually understand their options, they’re more likely to engage and choose wisely.

3. Turn benefits into stories people relate to

When it comes time to choose benefits, numbers and features are great, but a narrative sticks. Grounding benefits in a one-sentence story can help employees more easily wrap their heads around what would otherwise just be jargon.

Try things like this:

• “Alex saved $400 in medical costs by choosing the HSA plan for her growing family.”
• “Ken’s pet insurance helped cover his dog’s surgery after a squirrel-chasing misadventure.”

These real-world examples don’t just make benefits more relatable, they make them more memorable.

4. Prioritize visuals to drive engagement

Design isn’t just about making things look good. Thoughtful design makes information easier to find, understand, and act on. But HR professionals aren’t graphic designers and shouldn’t be expected to be. That’s why it’s important to partner with design experts.

These professionals know how to turn complicated benefits information into engaging and accessible materials for your employees, like intuitive charts, infographics, or short video explainers. Effective design simplifies complex information.

A well-designed benefits guide or public benefits website — one that strategically uses colors, layouts, icons, and more to direct employees and help them understand the information — can turn an intimidating or overwhelming process into an approachable and empowering one. And that all adds up to smarter benefits decisions from employees.

5. Show up where your employees are

Your workforce isn’t waiting around. They’re juggling meetings, incoming work tasks, and a whole life outside of work. Diversify your approach:

• Email and SMS updates engage employees on the channels they use.
• Virtual benefits fairs offer an interactive way to learn about benefits.
• Ongoing benefits education like Benefits U can boost utilization, increase satisfaction, and promote better health outcomes.
• A public benefits website give employees a deep dive at their own pace.
• Custom benefits videos help you communicate benefits topics in engaging ways.

You can use analytics from previous enrollment cycles to understand what channels resonate most with your workforce. But to really capture your employees’ attention, consider a full annual enrollment communications plan tailored to your people and your organization.

6. Listen, act and close the feedback loop

We’ve all filled out those surveys that disappeared into some digital void. That’s not how you build trust. Trust grows when employees see that their input is valued and acted on.

But meaningful feedback isn’t just about sending out a quick survey with a few questions about annual enrollment. It’s about uncovering the insights that help you drive change.

Instead of guessing which questions to ask or struggling to make sense of generic survey tools, it’s worth partnering with experts. From communication audits to benchmarking, the bswift Engagement Agency specializes in research and measurement. We can help you go beyond surface-level feedback.

But don’t keep what you’ve learned to yourself. Share what you’ve learned with employees. Show them their voices matter. Nothing says, “We care,” quite like actually listening.

A ripple effect across workplace culture

Investing in better communication doesn’t just improve annual enrollment outcomes. Transforming enrollment communication might sound like a lofty goal, but it’s achievable with the right strategies. And it can improve your company culture, too.

When you focus on improving connection and clarity in annual enrollment communications, it’s an investment in trust. And that trust ripples through your workforce, boosting morale, retention, and even productivity.

Try implementing one or two of the ideas from this post and see what happens. Better yet, connect with the bswift Engagement Agency. We’ll help you build trust, create stronger connections, and see lasting results.

[LET’S TALK]