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As CEO, editor in chief and Co-Founder of Charter, Kevin and his team have built Charter to be the leading voice on workplace transformation – not just with thoughtful research, but also with actionable resources and tools. Most recently, they published a playbook on Intergenerational Fluency 101, in partnership with Medley.
During this Medley Moments, we hear more from Kevin on how his own journey (having previously served as the founding editor in chief and Co-CEO of Quartz, a Senior Editor for The New York Times, and Managing Editor of The Wall Street Journal Online) has influenced his points of view on how individuals and organizations alike should think about ‘Leading Across Generations.'
A: I worked at The Wall Street Journal for 16 years as a correspondent in Paris and San Francisco, covering Silicon Valley. Later, I became Managing Editor, leading the journal's digital efforts. After that, I was part of the founding team at Quartz. I was trying to understand how to be a good leader and manage a team, eventually leading an organization of hundreds of people. What I found was that the existing sources of information and leadership frameworks didn’t really align with where the world was headed.
We’re dealing with big challenges: sustainability, inclusion, reinventing capitalism, the future of work amid automation, and a multigenerational workforce. The tools I had didn’t help me lead in ways that aligned with these realities. So, after leaving Quartz and working on a project at The New York Times on economic inequality, I came out of 2020 thinking that this was the moment to build an organization that provides resources for managers and leaders. Charter was born from that — starting with an email newsletter that quickly gained traction. It became clear that there was demand for something like this, and we could build a company around it to help bridge research and practice in leadership and management. We aim to help create fair, dynamic workplaces where people can thrive and innovate. And to me, fairness is foundational to that.
A: There were several moments at Quartz when the traditional frameworks I had were failing me. One example is running meetings. I realized that creating a culture of inclusion in meetings required more than what I had been taught. Another example was around compensation — it wasn’t always fair that people doing the same job were paid differently based on location or role. These structures weren’t serving me, so I started interrogating them.
I looked for answers, and found that there are alternative approaches out there — like salary transparency and non-negotiation job offers, which can help remove some of the advantages that more represented groups often have.
These insights weren’t widely available, but as I began to uncover them, I saw that there was a need to bring this knowledge to leaders more broadly. The responsibility to lead effectively — and fairly — required me to learn more and question established norms.
Q: You’ve highlighted something crucial — leaders need to know what they don’t know and be willing to learn. I also heard you emphasize the importance of driving decision-making with fact, data, and fairness. Let’s talk about intergenerational differences. I recently learned that there are currently five generations in the workforce, from Baby Boomers to Gen Z. Intergenerational fluency is a key area of focus. Can you define that term for us?
A: Intergenerational fluency, especially in a leadership context, is the ability to work across generations with effective feedback, communication, and understanding. It’s about allowing people to do their best work.
At its core, intergenerational fluency is really about communication — but breaking down assumptions about different generations and opening up conversations to foster mutual understanding.
A: It’s both. The way you speak to people influences what they’ll say to you and how they’ll respond. For example, I recently spoke with someone whose workplace had a generational divide over laptops in meetings. Younger workers would open their laptops to take notes, but older workers found it frustrating. This tension had existed for a while, but once they created space for a conversation, the situation improved. So, the first step is opening that space for communication. Another key is signaling openness to feedback. Leaders often unconsciously signal that they aren’t open to feedback from younger generations. Creating a culture where everyone feels they can contribute is vital.
A: Sure. One of the key insights from our research is that good leadership practices are consistent across generations. These include empathetic leadership, flexibility, and inclusion. We know that different generations have different needs, especially when it comes to benefits and work-life balance. But at the core, it’s about practicing inclusion and fostering a culture of open feedback and communication.
Some of the specific tactics we emphasize include reverse mentoring, where younger workers mentor senior leaders, and the use of user manuals — where employees share how they like to work and their preferences. These tools help bridge generational gaps by creating mutual understanding.
A: It’s a great question.
I think it’s important for new employees to recognize that good leaders appreciate feedback, even if it’s not always easy to give. Find opportunities to offer constructive feedback to leaders in a way that can improve the workplace for everyone.
It can be daunting, but if done well, it helps create the culture of communication and openness that’s so important.
A: So much of the challenge in multigenerational workplaces comes down to communication. It’s about creating space for open conversations, being willing to listen, and being open to giving and receiving feedback. If we can get that right, we unlock incredible opportunities for learning and growth across all generations. Thank you, Edith, for this conversation and for your partnership in creating the Intergenerational Fluency Playbook. It’s been a pleasure working with you and Medley.
