Benefits Without Borders: Enabling Choice in a Fluid Work Economy

Insights from an intimate gathering of Fortune 500 CHROs, innovative startups, and organizational psychologists on the future of work

In a dimly lit Minneapolis restaurant, an unusual conversation was taking place. Around a single table sat HR leaders from organizations such as Best Buy, Ford, Google, and Medtronic alongside startup CEOs building the future of benefits and workplace psychologists studying what makes employees thrive. The topic that emerged as the evening's throughline wasn't artificial intelligence or remote work—it was something more fundamental: employee agency.

As one executive put it during the evening's "sweet and sour" introductions, "I could leave my corporate role tomorrow if I wanted to, theoretically, but I can't, because... health care, right?" This moment of vulnerability crystallized a truth that resonated across the table: even highly successful professionals feel trapped by the systems meant to support them.

The Hidden Cost of Benefits Dependency

The research presented that evening by organizational psychologists Dr. Shonna Waters and Dr. Erin Eatough from Fractional Insights revealed a startling statistic: 81% of people make their stay-or-leave employment decisions based on healthcare benefits. Even more concerning, their study of over 1,000 U.S. workers metriced on their Angst Index found that 44% answer "no" when asked if they feel safe, can develop, or matter at their organization—creating what they term "workplace angst" that costs the average Fortune 1000 company $240-330 million annually.

One provocative insight came from Chris Ellis, CEO of Thatch, who shared a personal anecdote that illustrates the broader systemic problem. When his wife was pregnant, she researched the best OB-GYNs in their area, only to discover her preferred doctor wasn't covered by her company's insurance plan. "That experience where you empower the employee to have that freedom of choice," Ellis explained, "you feel much more connected to what you're offering to them."

This might sound like an issue of convenience, but it’s about something much more foundational. It's about psychological safety and autonomy, two of the three core human needs that drive workplace engagement. When employees lack agency over fundamental aspects of their security (like healthcare), it creates a dependence that constrains career mobility and decision-making.

Beyond Healthcare: The Broader Agency Revolution

The conversation revealed that healthcare is just one dimension of a larger transformation toward employee agency. Bijal Shah, CEO of Guild, shared how her company's partnerships with employers like Target are reimagining professional development. Target runs a nursing program despite not hiring nurses, recognizing that building resilient, capable employees—even if they eventually work elsewhere—creates a stronger workforce ecosystem.

"Companies we've seen do this really well are ones who take off those blinders and say, 'I'm not necessarily going to need all these people in the future, so how can I get them prepared for what might come next?'" Shah explained. This represents a fundamental shift from viewing employees as resources to be retained to viewing them as whole human beings to be empowered.

The psychological impact of this shift cannot be overstated. As the research showed, providing relevant learning and mobility opportunities:

• Reduces workplace angst by 4.1x

• Improves mission motivation by 13x

• Improves employee advocacy by 22x

• Reduces talent poachability risk by nearly 4x

The Service Now Model: Alignment Over Opposition

Perhaps the most compelling example of agency-driven thinking came from a case study of ServiceNow's approach to AI adoption. Faced with employee resistance due to job security fears, the company made a radical promise: any employee who eliminated their own job through AI automation would be promoted.

"This is a fundamentally different approach," Waters noted. "It aligns employee interests with organizational interests by making automation a competitive advantage for workers, not a replacement threat."

This example illustrates what the researchers call "psychological ergonomics"—designing work systems that align with rather than fight against human nature. When employees' survival instincts and organizational goals are positioned as oppositional, companies end up fighting basic human psychology.

The Service Now Model: Alignment Over Opposition

One of the evening's most sobering insights was what the researchers termed "altitude sickness"—the tendency for executives to become increasingly disconnected from frontline employee experiences as they rise in organizations. The data showed that the higher someone gets in an organization, the less visible workplace angst becomes.

A financial services veteran at the table shared his own experience with this phenomenon. When tasked with solving internal mobility challenges, he discovered that senior leaders couldn't believe the cultural barriers that junior employees faced. "There was such fear in the system that people wouldn't even have conversations about mobility because it was viewed as being disloyal," he recalled.

This blindness becomes particularly dangerous during times of transformation. As one dinner guest noted, the company had to eliminate 25% of its instructional design roles as AI tools made traditional approaches obsolete, yet maintained its mission-driven narrative without fully addressing the psychological reality for remaining employees.

Building the Future: Three Pillars of Employee Agency

The evening's conversations pointed toward three foundational elements for creating more agency-driven organizations:

1. Portable Security: Moving beyond employer-dependent benefits to systems that travel with employees. This includes not just health insurance portability, but also retirement savings, professional development accounts, and career credentials that maintain value across organizations.

2. Transparent Growth Pathways: Creating development opportunities that explicitly prepare employees for future roles, whether within the current organization or elsewhere. This requires moving past the fiction that all employees will (or should) stay indefinitely.

3. Psychological Safety in Transition: Designing communication, performance management, and change management systems that acknowledge rather than ignore the common human experience of workplace uncertainty: fear and self-protection.

The Competitive Advantage of Empowerment

As the evening drew to a close, one theme became clear: organizations that embrace employee agency aren't just doing the right thing—they're gaining a competitive advantage. In an era where talent is mobile and information is transparent, companies that empower rather than constrain their people will attract and retain the best performers.

The shift requires courage from leadership. As one CHRO noted, "We have so much power when we come together... These conversations can really make a difference." But it also requires systems thinking—recognizing that individual policies around benefits, development, and communication either reinforce or undermine employee agency.

The future belongs to organizations that view employee empowerment not as a threat to retention but as a pathway to engagement. In a world where the average tenure continues to shrink and skills evolve rapidly, the companies that thrive will be those that prepare their people not just for their current roles, but for their entire careers—wherever those careers may lead.

The question isn't whether this shift toward greater employee agency will happen. It’s already happening. The question is whether your organization will lead it or be left behind by it.

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This article is based on insights from an HR Elevate dinner featuring HR leaders from Fortune 500 companies, alongside startup leaders from Guild and Thatch, and organizational psychology researchers from Fractional Insights.