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Are your employees using the benefits you’re paying for?

09 Sep 2026

You built a benefits package that looks good on paper: health coverage, an EAP, a 401(k) match, maybe a wellness stipend. But a benefit only does its job the moment someone remembers it exists and knows how to use it. Without adequate communication, it's a line item in a packet nobody's opened since their first week.

The real return on a benefits budget doesn't entirely depend on what's in the package. A stronger health plan doesn't help if no one remembers the deadline to add a new baby. A good EAP doesn't help if nobody thinks of it during an actual crisis. Communication is the part that decides whether the benefits improve your employees' lives or go unused.

We’ll demonstrate this by following one hypothetical employee through a year of the moments where this either works or falls apart.

Day one

With a new laptop, a badge and an org chart of names they won't remember until week three, a new hire’s day is already full. Somewhere in that stack is the benefits packet: health plans, deductibles and an EAP number, maybe a wellness stipend, all explained briefly in an orientation meeting.

That's usually the last time benefits come up until open enrollment, months away. By then the details from day one are gone, and the packet is wherever new-hire paperwork goes to be forgotten. The explanations arrived at the one moment nobody was in a position to actually absorb it.

Life events

Major life events such as a new baby or another stressful family situation are exactly when a benefits package is supposed to prove its worth. But when a major upheaval happens like this, most employees aren’t thinking of digging through their new hire packet to see if there’s something that can help.

The information was never purposefully hidden. It just lived in a packet handed out on the first day, filed away and forgotten well before anyone needed it. If there's a deadline to add a dependent, a link to file a claim or a number to call, finding any of it takes longer than it should. This means that the benefits which were supposed to make life easier for your employees aren’t helping.

Renewals

A year later, the plan renews. Somewhere behind the scenes, a deductible went up, a covered medication changed tier or a network provider dropped off the list. Companies will usually send out this information by email, but there’s not always follow-up to make sure everyone opened and read the information.

Policy changes are the most disruptive when they are surprises. Many times, the first time employees learn about these changes is at the pharmacy counter, or at the doctor's office, when the coverage they've been quietly counting on all year isn't what it used to be.

Unexpected deadlines

Some life events start an invisible countdown. Getting married starts a deadline to add a spouse to a plan. Turning 65 necessitates a decision about whether to enroll in Medicare or stay on the company plan — a timeline that has nothing to do with open enrollment and everything to do with a birthday nobody in HR is tracking. Having a child age out of your family insurance or getting divorced also affects employee benefits.

None of these deadlines show up on a shared calendar. They exist entirely inside policies that employees might not know about. The standard once-a-year reminder about benefits does nothing for a window that opens and closes on nobody's schedule but the employee's own.

The question with nowhere to go

At some point in all of this, employees are going to have questions. Is this specific procedure covered? Can a partner be added outside open enrollment? Is the EAP actually confidential? None of it feels complicated enough to file an HR ticket over, but it's not simple enough to just guess at either.

So the question goes to whoever seems like they might know — a manager, a coworker who dealt with something similar once, a company Slack channel. Sometimes that gets close to the right answer. Often it doesn't. Either way, the employee never actually reaches the person whose job it is to know for certain.

How Highstreet can help

How your benefits help every one of these moments is information that got explained once to someone who wasn't ready to hear it. Giving employees the information they need when they need it requires more than better emails.

Your Highstreet agent can build you a solid communication plan. We know how to turn a benefits packet into an ongoing conversation, so your employees find out about a change from you, not from the pharmacy counter.

If your team could use a real communication plan instead of a once-a-year email, let's talk.

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  • Employee wellbeing