Benefits Open Enrollment: More Than a Checkbox, It's a Culture Signal

Every fall, inboxes fill with reminders: It’s time to enroll in your benefits. HR teams scramble to update documents, host webinars, and answer questions. Employees skim emails, click links, and hope they’re making the right choices.

But Benefits Open Enrollment isn’t just an administrative cycle—it’s a moment of truth. It reveals how well we communicate, how much we care, and how seriously we take the real lives of the people who work for us.

Benefits Are Personal—Treat Them That Way

Behind every benefits decision is a story:

• A parent choosing a plan that covers therapy for their child

• A young professional weighing HSA options for the first time

• A caregiver navigating leave policies while supporting a loved one

When we treat enrollment like a transactional task, we miss the opportunity to connect. When we treat it like a moment of care, we build trust.

HR’s Role: Translators, Advocates, and Culture Builders

Benefits are complex. Deductibles, coinsurance, out-of-pocket maximums—it’s a lot. HR’s job isn’t just to administer—it’s to translate:

• Make it human: Use plain language, real examples, and empathy

• Make it inclusive: Ensure materials reflect diverse needs and family structures

• Make it accessible: Offer multiple formats, languages, and support channels

And most importantly, make it strategic. Benefits are one of the biggest investments a company makes in its people. Let’s treat them like the culture-shaping tools they are.

What Employees Really Want During Enrollment

It’s not just about plan details—it’s about feeling informed, supported, and seen. Employees want:

• Clear comparisons and decision tools

• Timely reminders without overwhelming messaging or information

• A sense that their needs were considered in plan design

• A human to talk to when things get confusing

If we get this right, enrollment becomes more than a deadline—it becomes a demonstration of care.

A Moment to Reinforce Values

I’ve led open enrollment in organizations where it felt like a burden—and in others where it became a celebration of employee well-being. The difference? Leadership that saw benefits as part of the employee experience, not just a cost center.

Open enrollment is a chance to say: We see you. We support you. We’ve got you covered.

Let’s not waste it.

About the Author

Andrea Lucky is the CEO | Founder of Silver Fern HR Consulting, a firm dedicated to transforming workplace cultures and driving strategic growth. With deep expertise in organizational transformation, talent strategy, and leadership development, Andrea partners with companies to align their people operations with their vision and business goals.

Known for her ability to shape cultures that inspire engagement and innovation, Andrea helps organizations navigate change, strengthen leadership effectiveness, and build workplaces that empower employees at every level. Her experience spans industries, with a strong focus on helping businesses create sustainable talent strategies that support long-term success.

With a keen eye for aligning strategy with impact, Andrea guides organizations in translating bold visions into actionable workforce solutions. Whether leading complex transformations or refining leadership frameworks, she is passionate about driving meaningful change that positions companies for lasting success.

Follow Andrea for insights on workplace culture, leadership, and the future of people strategy.