A patient walks into a doctor’s office complaining of a persistent stomach ache. A traditional healthcare package might lead to specialists, scans, and tests, but what if the real issue isn’t physical at all? 

“If they’re able to talk about it, and they’re able to really understand what’s going on with them from a mental standpoint, behaviorally, it may just be they’re dealing with stress and anxiety,” said Joan Kronick, the VP of sales at One Medical. 

This story highlights a critical disconnect in today’s workplace, where the systems designed to support employees—from healthcare to benefits packages—are often incongruent with the lived experiences of a workforce that now spans five generations. Kronick spoke with other executives on the matter during a panel discussion at From Day One’s Midtown Manhattan conference. 

It Starts With Care

Jillian Morgan, the director of community and wellness at IPG Media Brands, saw her transition into a corporate role as a licensed clinical social worker as a natural evolution since both roles revolve around care. 

“We think about the human experience and the value that is inherent in every single being,” Morgan said. “Caring for your employees is essential. They are the backbone of your company. It’s not optional to take care of your employees, because you need them to thrive.”

This philosophy set the tone for the panel discussion moderated by Tania Rahman, the social media director at Fast Company. The conversation, titled “Inclusive Well-Being Strategies for a Multigenerational Workforce,” brought together leaders from HR, benefits, and wellness departments to tackle a central question: how can companies design wellness strategies that meet everyone’s needs in an era that spans five generations of workers, from Gen Z to Baby Boomers. 

Morgan says the answer starts with a simple practice. “Listen first, design second,” she said. “Don’t assume the needs. Find out what the needs are.”

Start by Listening, Then Listen Some More

The panelists all agreed that the foundation of any successful employee well-being strategy is a robust, multi-layered approach to employee listening. “People want to be seen, they want to be valued, and they want to be heard,” Morgan said. “So what are the spaces we create to actually listen?”

Marina Vassilev, the VP and head of total rewards for North America at Schneider Electric, employs a variety of channels. “We use multiple channels of listening, pulse surveys, total reward surveys that we run every couple of years [in addition to] focus groups,” she said. “We have close partnerships with our employee resource networks, because they give us a great opportunity to understand any unmet needs of a specific group.”

Alain Bernard, VP of corporate HR at Quest Diagnostics, emphasized the importance of equipping leaders to listen during team huddles and leveraging mobile technology for feedback. 

Jon Lowe, chief people officer at DailyPay, offered a more direct method. “Spend time with your frontline employees,” he urged, recalling his time at Amazon. “I typically would pack boxes during the holiday season.”

Identifying Commonalities in a Diverse Workforce

While it’s essential to understand generational differences in the workplace, all employees share the same fundamental needs. “We’re not all that different anyway,” Bernard said. “When you really talk to people at the heart of the matter, you look at the financial crisis that people are dealing with. You look at the mental health challenges coming out of Covid.”

Three areas consistently rose to the top during the conversation: mental health, flexibility, and financial wellness. Vassilev agreed, these needs manifest differently across generations, so a one-size-fits-all approach often fails. “From a benefits perspective, it sometimes manifests itself differently for financial well-being,” she said. “The offer that we have for individuals who are just joining the workforce is very different. We’re looking at student loans and credit card debt and saving for a mortgage, and then the individuals who are close to exiting the workforce need a lot of retirement consulting and advice.”

Evolving Beyond an Outdated Benefits Model

The conversation focused on moving beyond traditional benefits packages. Lowe challenged the audience to think more creatively about ways to deploy finite resources. “Dollars are fungible, right? And so the way that we seek to go and deploy those doesn’t have to fall into the traditional mold of what benefits are supposed to look like,” he said.

Lowe questioned whether conventional offerings like vision care were as valuable to some employees as a streaming service subscription or a childcare subsidy would be. “If you understand the journey that your people are on, then you can start to go and figure out on that barometer of what creates the highest degree of utility for the scarce amount of resources that we have.”

Benefits packages that allow holistic care and encourage preventive care, allowing employees to take ownership of their health journeys are essential, says Kronick. 

Determining if benefits programs are effective requires a mix of real-time feedback and data mining. Benard pointed to utilization rates, vendor management, and feedback. Vassilev described having success with large, anonymous virtual focus groups that even included manufacturing employees. 

The Role of AI in Mental Health

Rahman cited a 2025 study that showed 49% of AI users who report mental health challenges use major large language models (LLMs), such as ChatGPT, Gemini, or Claude for therapeutic support. Around 63% of these people report that using LLMs improved their mental health, while 36% found AI programs more effective than human therapists. 

“It allows people to remove the stigma of having to ask for help,” Morgan said. However, she cautioned that AI lacks the nuance of a trained professional and should be used to navigate people to the right human help, not replace it. AI is used at One Medical as a tool to help providers listen more intently and transcribe conversations, not for diagnosis, says Kronick. 

Ultimately, to improve workplace well-being, Kronick emphasized grounding decisions in real evidence: “Look at your clinical data, really understanding where your employees are spending their time.” Vassilev agreed, highlighting the importance of employee listening. “Think about it holistically,” she said. 

Ade Akin covers artificial intelligence, workplace wellness, HR trends, and digital health solutions.

(Photos by Josh Larson for From Day One)