The Charter Leadership Forum is a roundup of guidance from the greatest minds in talent. For each edition, Charter’s research team asks expert practitioners to share their insights around the biggest questions shaping the changing world of work.
With five generations now sharing the workplace, leaders face an unprecedented mix of values, habits, and expectations. Although those differences can create friction or misunderstanding, they can also be a powerful source of learning, innovation, and resilience. We asked leaders how they’re building workplaces that bridge generational divides, turn tension into creativity, and design cultures where every age group can contribute and grow.
How can leaders move employees beyond generational stereotypes—about Gen Z being restless or Boomers being resistant—to focus on shared purpose and learning?
Lorraine Stomski, Chief Talent Officer, Walmart: Being aligned around a common purpose and values helps break through generational differences. At Walmart, that purpose is to help people save money and live better. One of the secrets to Walmart’s success is the concept that good ideas come from everywhere in our company. One of our core values is “respect for the individual” and that transcends age, tenure, education level, whatever it may be. There’s an expectation that leaders from throughout our company spend time visiting our stores and supply chain facilities on a regular basis. Whether you’re in operations, technology, merchandising, people or anywhere else, one of the best ways to learn what’s working and what can be better is by hearing from the associates who are closest to our customers.
Kit Krugman, SVP, People and Culture, Foursquare: What I can say with confidence: we are in an era where the gravitational pull to label, categorize, and therefore stereotype and misjudge people or groups feels more rampant than ever. Are peoples’ behaviors shaped by the macroeconomic environment? Absolutely. Are they shaped by the technological forces they interact with? Absolutely. Are they shaped by the social systems they participate in and or surround them? Absolutely. Are they also shaped by their identity, location, individual traits and characteristics? Absolutely. I feel like by even talking about “generations” in the workplace, we have lost the plot and flattened the conversation.
Carly Roszkowski, Vice President, Financial Resilience, AARP: Leaders must actively challenge stereotypes—such as Gen Z being restless or boomers being resistant—by highlighting shared goals and fostering inclusive dialogue. Research shows that mixed-age teams thrive when everyone’s contributions are valued. Rituals like cross-generational mentoring, collaborative projects, and open feedback sessions help build trust and curiosity. Focusing on shared purpose and continuous learning, rather than age-based assumptions, unlocks creativity and resilience across the organization.
How do benefits, flexibility, or feedback systems need to evolve to meet diverse generational needs?
Andy De Marco, Chief Human Resources Officer, Fujitsu North America: While conventional wisdom suggests that feedback expectations vary by generation, with Millennials and Gen Z often seeking more frequent and real-time input, the underlying driver may be less about age and more about the way work is changing. Digital-native employees are accustomed to instant information, but the pace of business now requires all of us to operate on shorter learning cycles.
At Fujitsu, we see real-time feedback as essential for every generation. It helps teams stay aligned to customer expectations, service performance and emerging opportunities. At the same time, we still anchor performance conversations with focused quarterly check-ins. Those moments of reflection give people space to step back, review outcomes, and challenge themselves for the quarter ahead. It’s a combination of continuous feedback and structured reflection that meets the needs of a multigenerational workforce.
Lorraine Stomski, Chief Talent Officer, Walmart: It’s funny, across our 2.1 million associates, I find we’re more alike than we are different. Every generation expects to be heard. Technology, including AI, makes listening at scale more efficient than ever before, from data analysis to AI-powered suggestions on next steps for leaders. AI can help deliver personalized results, but the most important work is how our leaders dig in with their teams, host transparent conversations and work together to address opportunities for improvement.
Carly Roszkowski, Vice President, Financial Resilience, AARP: Benefits and systems must be adaptable. Flexibility in work arrangements—such as remote or hybrid options—supports caregivers and those seeking work-life balance. Feedback systems should be continuous and multi-directional, allowing all voices to be heard. Benefits that address financial resilience, health, and lifelong learning appeal across generations. By evolving these systems, organizations can attract and retain talent at every stage of life, ensuring everyone feels valued and supported.
Kit Krugman, SVP, People and Culture, Foursquare: Listening to people to genuinely understand who they are, what drives them and what they value. Resisting the urge to categorize someone as a Boomer or a Millennial, etc. My boomer dad is more technologically savvy than many individuals who may be categorized as Gen Z.
What rituals or recurring practices help build trust and curiosity across age groups?
Lorraine Stomski, Chief Talent Officer, Walmart: Trust grows through transparency and shared learning. I love attending our quarterly anniversary milestone celebrations where associates who have been with Walmart 20, 30, 40+ years share their stories. These are the people steering our culture and shaping the next generation of associates. The size of our associate base means we get to work across all generations, from high school students to associates who join Walmart after completing another career. They all have something to offer that enriches our culture and our business.
Kit Krugman, SVP, People and Culture, Foursquare: I’m currently reading David Brooks’ new book: “How to know a person” and I cannot recommend it more highly for this exact question. Genuine, selfless inquiry into what matters, motivates, shapes and inspires someone will always be the foundation of strong relationships, regardless of “generational” differences.
Carly Roszkowski, Vice President, Financial Resilience, AARP: Regular cross-generational mentoring, team huddles, and knowledge-sharing sessions foster trust and curiosity. Celebrating diverse perspectives in meetings, encouraging open dialogue, and rotating leadership roles in projects help break down barriers. AARP surveys of older and younger workers find that when organizations create space for informal learning and recognize contributions from all ages, teams become more innovative and resilient.
Where have you seen reverse mentoring work well—and where has it fallen flat? What makes the difference?
Andy De Marco, Chief Human Resources Officer, Fujitsu North America: Reverse mentoring has been especially effective when new skills or new ways of working emerge, largely around novel technology topics. Earlier in my career, I facilitated programs where employees with stronger digital fluency supported more tenured colleagues as online channels became central to how we work. It succeeded because both sides gained something: senior employees built confidence, and newer talent benefited from the questions and strategic lens of experienced leaders.
Where it falls flat is when it’s positioned as a one-way transfer of knowledge or rushed as a quick fix. Success requires thoughtful matching, time to build trust, and a shared understanding of what both participants want to achieve.
Today, with expectations and tools evolving faster than ever, we often see the best results from mixed-level teams collaborating on real business challenges and real use cases. When different experience levels work side by side on a common goal, learning becomes mutual and progress accelerates.
Carly Roszkowski, Vice President, Financial Resilience, AARP: Reverse mentoring thrives when it’s structured, reciprocal, and supported by leadership. Success comes from clear goals, mutual respect, and recognition of the unique strengths each participant brings. It falters when treated as a one-way street or when age-based biases persist. The difference is a culture that values learning from every generation and sees mentoring as a partnership, not a hierarchy.
Lorraine Stomski, Chief Talent Officer, Walmart: I tend to think reverse mentoring is a bit of a misnomer – like all mentoring, the goal is for both participants to walk away with new perspectives, insights and a durable relationship that’s mutually beneficial. People jump to AI and technology as a focus area for reverse mentoring, and it’s true that our early-career associates are often digital natives. But I think the real value is anyone who has fresh eyes on how we do things – and that can be at any stage, whether someone is new to the role, new to Walmart or new to their career. We always reserve the right to get smarter, and we have a culture where ideas truly come from everywhere.
Kit Krugman, SVP, People and Culture, Foursquare: I believe reverse mentoring is most effective when both participants opt into it enthusiastically and genuinely want to learn from each other. If either participant believes they have more to give than to get, the conversation shifts from one of humble inquiry to judgment and condescension. In addition, clarity on gaps and/or what you’re looking to learn is always invaluable in setting any coaching up for success. Starting the relationship off with some “contracting” around what each party hopes to gain will help drive clarity and value.