Five questions to ask before open enrollment begins

A thoughtful approach to helping employers turn enrollment planning into better benefits strategy

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Open enrollment comes with a long to-do list. But before your employer clients get too far into plan details, deadlines, and employee communications, there’s a bigger conversation worth having: Do the benefits they’re offering still make sense for the workforce they have today?

That question has become more important as healthcare costs have risen, employee expectations have evolved, and the range of benefits employers can offer has grown. Employers have more ways to support their people, but they also have more decisions to make about where their benefits dollars will have the greatest impact.

As a benefits administrator, you have a useful vantage point for seeing how employees actually use their benefits. Bringing those insights into open enrollment planning can help clients make more informed choices.

Here are five conversations worth having with clients as they prepare for open enrollment.

1. What are employees telling us through their behavior?

It’s easy for benefits planning to become an exercise in looking at what was offered last year and deciding what needs to change this year. But your clients may already have useful evidence about what’s working, and what isn’t.

Enrollment, participation, and account behavior can all help tell that story. So can employee surveys, questions coming into HR, and changes in the makeup of the workforce.

Help employers look for patterns. Are eligible employees passing on an HSA or FSA? Are they enrolling but contributing very little? Are certain benefits consistently underused? Have employees’ needs changed as the workforce has changed?

The answers won’t always be obvious. Low participation doesn’t necessarily mean employees don’t value a benefit. They may not understand it. They may be worried about contributing too much, or the benefit may simply not fit their needs. That distinction matters — before an employer changes the benefit itself, it’s worth understanding the problem they’re trying to solve.

2. Where are employees feeling the most financial pressure?

Affordability is one of the biggest challenges facing employers and employees alike. And employees don’t experience healthcare costs as a single number. They experience the deductible they have to meet each year. The prescription they weren’t expecting. The orthodontia bill, the urgent care visit, or the recurring cost of managing a chronic condition. Outside of healthcare, they may also be balancing childcare, commuting, and plenty of other everyday expenses.

That makes open enrollment a good time to look at the entire benefits package through an affordability lens. For example, could an employer contribution to an HSA or HRA help offset greater cost-sharing elsewhere? Are employees making full use of the tax advantages available through an FSA or HSA? Does the account strategy complement the medical plan design? Are contribution levels realistic for employees across different income levels and life stages?

These are areas where partners can bring valuable perspective. Health benefit accounts shouldn’t be considered in isolation from the rest of the benefits package. They can be part of a broader strategy for helping employees manage the costs they’re responsible for.

3. Would more benefits truly create more value?

The benefits landscape has expanded considerably. In addition to traditional medical coverage and health benefit accounts, employers may be considering voluntary benefits, mental health resources, family-building benefits, lifestyle accounts, condition-specific programs, and other targeted offerings.

More choice can be a good thing. But adding another benefit doesn’t automatically make a benefits package better.

As your employers add more targeted benefits, you can help them think through the tradeoff between greater choice and greater complexity. Does a new offering fill a meaningful gap? Does it complement what’s already available? And can employees easily understand when and why they would use it?

This is especially important for a workforce that can look very different from one employee to the next. A new graduate, a parent with young children, an employee managing a chronic condition, and someone approaching retirement may view the same set of benefits very differently.

The goal doesn’t have to be offering everything to everyone. It’s giving employees enough flexibility to find value in what their employer provides, without creating so much complexity that the value gets lost.

4. What do we want to accomplish this enrollment season?

“Successful open enrollment” can mean a lot of things. Getting everyone enrolled on time is certainly one of them, but it shouldn’t be the only one. Before enrollment starts, encourage employer clients to get specific about what they want to improve.

Maybe they want to increase HSA or FSA participation. Perhaps employees are enrolling in an HSA but contributing too little to get much value from it. The employer may want greater adoption of a particular plan, stronger utilization of an employer-funded benefit, or better engagement among a segment of the workforce that has historically been difficult to reach.

Once the goal is clear, you can have a better conversation about how to get there. If the objective is to increase HSA participation, for example, another HSA email may not be enough. Employer contributions, plan design, contribution guidance, and decision-support resources may all play a role.

5. What can this open enrollment teach us about the next one?

Once elections are complete, it’s tempting to declare open enrollment finished and move on. But some of the most useful information becomes available after the enrollment window closes.

Go back to the baseline you established at the beginning. What changed? Did participation or contribution behavior move? Did employees engage differently with certain benefits? And, most importantly, did the employer make progress against the goals it set?

Those insights can then inform the next round of benefits decisions, creating a continuous cycle: understand what employees need, design benefits around those needs, support enrollment, measure what happened, and improve. Over time, open enrollment becomes less of an annual reset and more of a useful checkpoint in an ongoing benefits strategy.

Help clients make open enrollment a strategy moment

Open enrollment presents a natural opportunity to have a bigger conversation with your employers — not just about what they’re offering this year, but why. By bringing data, account expertise, and a broader view of employee behavior to the table, you can help employers make more intentional decisions about where to invest, where to simplify, and what they want their benefits to accomplish.

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Ready to help your clients put that strategy into action? Use our Open Enrollment Checklist for practical steps to plan communications, equip employees with useful resources, and keep open enrollment on track.