One Open Enrollment, Four Generations

Open Enrollment (OE) is where the diversity of today’s workforce comes into full view: four distinct generations of employees, countless life stages and just one window of time to reach them all.

The challenge? What feels like a lifeline to one employee may feel irrelevant to another. Generation Z is looking for mental health support and financial footing. Millennials are juggling student loans, childcare and the cost of owning a home. Generation X is squeezed in the middle, caring for kids and aging parents. And Baby Boomers are planning for retirement while focusing on staying healthy and engaged.

The benefits themselves matter, of course. But how you communicate them is just as important. Employees need to see themselves in the message to act on it. Otherwise, they tune out. And during Open Enrollment, tuning out means missing opportunities to improve life at work and at home.

Four Generations, Four Different Conversations

Each generation has different priorities for which benefits matter most and preferences for how they want to hear about them, according to Mercer’s 2025 Health on Demand global survey of employees.

Generation Z (1997–2012):

Still early in their careers, Gen Z employees are highly focused on mental health, flexible work and financial confidence. Mercer reports nearly half (49%) are already worrying about cognitive decline, signaling that access to mental health resources will resonate strongly.

Short, digital-first communications and peer-to-peer storytelling work best.

Millennials (1981–1996):

Often raising young families while building careers, Millennials value financial wellness, childcare support and programs that help reduce day-to-day stress. Loan repayment, savings programs and hybrid work top their list of priorities.

Clear communication that cuts through benefit complexity and validates the pressures they face helps Millennials engage with OE communications.

Generation X (1965–1980):

Known as the “sandwich generation,” Gen X is managing kids, mortgages and caregiving for parents. Their biggest concerns are physical health decline and financial readiness for retirement.

They respond well to practical, straightforward information — especially on preventative care, eldercare resources and flexible scheduling.

Baby Boomers (1946–1964):

Boomers are staying in the workforce longer and bring stability and loyalty to organizations. They value strong healthcare coverage, flexible retirement options and simple navigation tools.

They’re less likely to want trendy digital campaigns and more likely to trust clear guides, in-person sessions or manager-led conversations.

Shared Priorities Across the Generations

All employees share concerns about healthcare affordability, financial security and work-life balance. Universal or core benefits like health coverage, paid time off and preventive care remain foundational to Open Enrollment offerings, and they are offered by 97% of employers, according to SHRM.

Worryingly, the Mercer global report states that 74% of employees globally feel physically and mentally well today, down eight points from 82% just two years ago. It’s therefore more imperative than ever to ensure communications about these core benefits flex by generation to ensure maximum impact.

How Communicators Can Bridge the Gap

Open Enrollment isn’t just about pushing out information. It’s about making sure employees can see themselves in the options. That requires tailoring communication with three key strategies:

1. Segment with purpose.

While it’s important to create a single destination where everyone can view the full scope of benefits options, audience segmentation is key. Leveraging generational brackets is a place to start your segmentation.

Think about Medicare reminders for Boomer or Gen X employees. Consider childcare resources for Millennials who are or are looking to become parents. Perhaps tuition reimbursement and student loan repayment information is more relevant for Gen Z hires. These communication segments will help to quell the fire hose of OE communications and increase message relevance.

When creating your segments, don’t forget to ensure employee data is robust and vetted so employees aren’t left out of their respective categories. Alignment between HR and internal communications teams is critical to making sure the right messages land with the right employees.

2. Tap into life moments.

Big life changes — like starting a family, buying a home or nearing retirement — are when benefits feel most meaningful. And employees want help here: Mercer states that 79% across generations say they’d welcome employer communication about preventive care and planning for future health and financial needs. Align communications with these moments so the right information arrives at the right time, not just during OE.

3. Balance tech with human connection.

According to Mercer’s survey on health and benefit strategies for 2025, 70% of employers believe AI-powered tools will help address first-line questions and provide navigation around benefits over the coming years. These tools can personalize guidance, but employers should tread carefully.

The sensitivity of financial and physical health often means employees would prefer to interact with a live human being. Nearly half of U.S. workers (48%) would prefer to learn about their benefits options from a person during OE — a five-point increase from 2024 — according to The Hartford. As always, technological efficiency needs to be built on a strong foundation of human connection. Offering office hours, webinars or manager support ensures technology never replaces trust.

Why It Matters

While Open Enrollment is by necessity a broad-brush communication moment, it doesn’t have to remain a check-the-box awareness exercise. Benefits are one of the strongest ways employers can demonstrate care and build trust with employees of all generations. In fact, Mercer’s Health on Demand report shows that employees who feel confident in their healthcare and benefits are far more likely to say they’re thriving at work.

That confidence comes not only from what’s offered, but from how it’s communicated. When benefit messaging connects to life stages, reflect generational needs and balance technology with the human touch, employees feel recognized as people, not just workers.

And that’s the real opportunity: to approach Open Enrollment not as a one-size-fits-all campaign, but as a moment to affirm that employees are the complex, nuanced individuals they are.

Contributors