Segal Benz Blog

6 Ways to Prioritize Well-Being at Open Enrollment

Written by Heidi Henderson | July 16, 2026

Open enrollment is more than a moment to choose benefits; it’s a critical opportunity to help employees understand, access, and use well-being resources throughout the year.

But for many, the open enrollment experience is overwhelming, filled with complex choices, unfamiliar terms, and fragmented information. Employees consistently report difficulty understanding and navigating their benefits and well-being resources, which often leads to missed opportunities for care and support.

That’s why open enrollment should do more than guide employees through plan selection. It should function as an orientation moment. A time to connect employees to the full range of benefits available to support their health, finances, and daily lives.

When well-being programs are positioned clearly and integrated into the broader experience, they can help employees take earlier action, reduce costs, and feel more confident using their benefits.

Here are 6 strategies for helping employees get more from your well-being resources.

1. Make Well-Being Part of the Bigger Benefits Story

Employees aren’t focused on your programs. They’re focused on their own personal experience. When well-being programs are presented separately, they often feel like optional add-ons. But when they’re tied directly to medical plans, preventive care, and financial health, they become part of a more meaningful story and experience.

In practice:

  • OE guides that show how preventive screenings and coaching can help avoid higher medical costs
  • Mental health support connected to everyday challenges, like stress, sleep, and productivity
  • Visual maps showing how benefits work together across vendors

The result:
A more integrated, human-centered experience, helping employees see how their benefits and well-being programs work together, not in silos. Open enrollment is also a moment to connect well-being to the broader total rewards story.

2. Prioritize Clarity Over Completeness

More information doesn’t improve decisions, clarity does. Many employees struggle to understand benefits and well-being programs because the communications are too complex, fragmented, or jargon-heavy. Employees often need clearer guidance to understand and use their benefits, not just more information.

In practice:

  • “Start here” enrollment journeys that simplify first steps
  • 60-to-90 second videos that explain key actions
  • Plain-language descriptions
  • Personalized checklists based on common needs or life stages

The result:
Streamlined, personalized communications that reduce overwhelming feelings and help employees take action

3. Make Every Day as Important as Enrollment

Enrollment is a moment. Well-being is an everyday experience. Too often, employees enroll in benefits but don’t know how to use them afterward, which erodes well-being.

In practice:

  • What-happens-next? guidance included in OE campaigns
  • Decision pathways showing where to go for care (virtual, urgent, primary)
  • Centralized benefits hubs that reduce vendor fragmentation
  • Mobile-friendly resources accessible to employees and families

The result:
A shift from static enrollment to dynamic, ongoing support, helping employees better navigate care, control costs, and engage with resources over time

4. Build Trust Through Clear Privacy Communication

Trust is a prerequisite for participation. If employees are unclear about how their data is used, they may avoid well-being programs altogether.

In practice:

  • Simple, visible privacy explanations embedded into communications
  • Who-sees-your-data-and-who-doesn’t messaging
  • Consistent language across vendors
  • FAQ-driven reassurance around participation and confidentiality

The result:
Stronger trust and increased engagement, especially in programs tied to sensitive health or behavioral data

5. Anticipate Questions and Remove Barriers Early

Uncertainty delays action. Employees are more likely to engage when they understand what to expect.

In practice:

  • Scenario-based FAQ (e.g., “What happens if I find a health issue?”)
  • Step-by-step program walk-throughs
  • Real-life examples of how people use and benefit from well-being programs
  • Live or digital Q&A support during OE

The result:
A more predictable, supportive experience that reduces confusion and builds confidence

6. Keep It Relevant, Personalized, and Whole-Person Focused

Well-being is not one-size-fits-all. Employees increasingly expect support that reflects the full scope of their lives—physical, mental, financial, and social.

In practice:

  • Life-stage messaging (early career, caregivers, nearing retirement)
  • Targeted outreach tied to financial stress, burnout, or health needs
  • Storytelling that reflects real employee experiences
  • Multichannel engagement across email, mobile, and manager touchpoints

The result:
More personalized, data-informed communication experiences that support and accommodate employees in their current situations

Turn Enrollment into Engagement

Open enrollment is often treated as a transactional process. But for employees, it’s a rare moment of attention, when they step back and consider how their benefits support their health, finances, and daily lives. That creates an opportunity. When benefits are simple and accessible, they drive better well-being outcomes.

When well-being is embedded in a clear orientation strategy, employees can move from uncertainty to confidence, and from selection to sustained action.

In a benefits environment defined by complexity, rising costs, and high expectations, communications aren’t just about awareness. They’re about helping employees make better decisions at open enrollment—building confidence to use their benefits to support their well-being every day.

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