The Best Open Enrollment Strategies Start Before Open Enrollment

8/31/26

As summer winds down, many employers begin turning their attention to open enrollment. Planning meetings are starting, communication timelines are taking shape, and decisions about benefits offerings and employee education are moving higher on the priority list.

While enrollment season often receives the most attention, the strongest enrollment outcomes are rarely built during the enrollment period itself. They are shaped by the experiences employees have with their benefits throughout the year.

By the time employees sit down to make enrollment decisions, they are not starting from scratch. They bring a year's worth of experiences with them, including:

A benefit that helped them through a difficult situation
An account they struggled to understand
A doctor visit that clarified how coverage works
A claim, prescription, or unexpected expense that prompted questions

Those experiences often influence enrollment decisions far more than any enrollment guide or presentation.

That is why the most effective employers do not think of open enrollment as the beginning of the benefits conversation. They view it as the result of ongoing efforts to help employees understand, appreciate, and use their benefits with confidence.

What employees learn between enrollment seasons matters

One of the biggest challenges employers face is that employees often do not fully understand the benefits they elected until they need to use them.

Throughout the year, employees may:

Use a Health Savings Account for the first time
Experience a life event and need support
Discover a wellness resource they did not know existed
Learn more about how their coverage actually works

These experiences influence how employees view their benefits and the decisions they make when the next enrollment season arrives.

The challenge is that many organizations focus most of their communication efforts around enrollment and spend far less time educating employees during the rest of the year. As a result, employees may:

Overlook valuable resources
Forget about available programs
Miss opportunities to get more value from their benefits

The best employers keep the conversation going

As a trusted benefits partner, we have seen that employers with strong benefits engagement take a different approach. They do not treat open enrollment as a once-a-year event. Instead, they create opportunities throughout the year to educate employees, answer questions, and connect people with the resources available to them.

Those efforts might include:

Helping employees better understand spending accounts
Sharing preventive care reminders
Promoting Employee Assistance Programs
Highlighting tuition reimbursement opportunities
Raising awareness of student loan repayment benefits

The goal is not to overwhelm employees with information. The goal is to make benefits easier to understand and easier to use. In many cases, a timely reminder or simple educational campaign can have a meaningful impact.

Good data matters, but conversations matter too

Enrollment reports can provide valuable information, including:

Participation rates
Plan elections
Contribution trends

However, they do not always show whether employees understand how to use their benefits.

Some of the most valuable insights come from listening and identifying patterns in employee feedback. Consider questions such as:

What questions come up most often?
Which benefits create confusion?
What resources are employees unaware of?
Which programs generate the most positive feedback?

The answers can reveal opportunities to improve communication, remove friction, and create a better benefits experience. In many cases, the solution is not adding another benefit. It is helping employees better understand the benefits they already have.

Preparing employees for better enrollment decisions

As enrollment season approaches, employers naturally focus on:

Plan design
Contribution strategies
Administrative preparation

Those activities are important, but they are only part of the equation.

It is also worth asking whether employees are prepared to make informed decisions when enrollment begins. Employees who understand their current benefits are often better equipped to evaluate future options because they know which resources they use most, which programs provide value, and where they may need additional support.

August can be an ideal time to reinforce benefits education before enrollment communications begin in earnest. Examples include:

Reminders about spending accounts
Spotlights on employee education benefits
Information about wellness resources
Answers to commonly asked questions

Small touchpoints today can help employees approach enrollment with greater confidence tomorrow.

Better enrollment starts with better engagement

At Lifetime Benefit Solutions, we believe the best benefits strategies focus on people first. Benefits are most valuable when employees understand them, use them, and feel supported throughout the year.

When employers invest in ongoing education and engagement, they help employees make more informed decisions during enrollment and get more value from their benefits long after enrollment ends.