Too Millennial: Unleashing the Next Generation of Leaders

Hosted by Jessy Grossman

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Jul 2026

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About the show

After countless sessions of leadership and team coaching, Jessy knows that leadership needs to be reimagined. Fueled by frustration with outdated work norms and clients on the edge of burnout, she's left with a desire for a better way. So this podcast is on a mission – a mission to explore what leadership looks like as Millennials, the "snowflake, entitled generation", grow up and step into prominent positions of influence. By interviewing a diverse range of guests, from seasoned executives to rising stars, who share their leadership stories we'll unleash the next generation of leaders.

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30 recent

July 8, 2026Episode 613 min

Are You Being Heard or Understood?

I teach communication. And yet getting my ideas out of my head and into words that other people can actually receive takes me a tremendous amount of effort. My brain jumps around. I say the same thing over and over making meaning as I go. My husband thinks before he speaks. I think while I'm speaking. It's like we speak completely different languages. The point is — communication is hard. Even for people who do this for a living. And most of us are making the same fundamental mistake: we think communication is about our ability to articulate. It isn't. Communication is a loop. A process of shared meaning-making. And the breakdown doesnt happen just because someone didn't speak clearly — it happens in the gap between being heard and actually being understood.

June 24, 2026Episode 550 min

Is Your Team Connected?

What a Sound Healer Knows That No Leadership Book Will Tell You One of the questions I get most from the leaders is some version of: how do I actually create connection on my team? How do I get people to open up, speak up, feel safe enough to say the hard thing? Psychological safety. Cohesion. Real connection. These are the foundations of every high-performing team — and most leaders have no roadmap for building them intentionally. So I went looking for someone who does this better thananyone I know. And the answer surprised me. Rachel Kathryn Weber is a Chicago-based energy healer, sound healer, and retreat facilitator who takes rooms full of strangers and has them feeling genuinely safe and connected within minutes. Her work looks nothing like corporate leadership development. And yet what she knows about creatingpresence, vulnerability, and real connection in a group is exactly what leaders say they want for their teams — and almost never know how to build. I've been in Rachel's spaces. I've shown up with my arms crossed, looked like I didn't want to be there, and come back every single time. This episode is about why. Plus: Rachel channels a closing song live on the podcast. I asked. She delivered. Find Rachel Kathryn Weber at: https://www.earthedempress.com/

June 10, 2026Episode 434 min

Why You Should Manage Like a Slacker?

Most managers are so focused on getting the work done, they never stop to ask: are we actually leaving room to do it well? In this episode, I sit down with Reid — engineering manager, deeply well-read, and someone who introduced me to a concept I now can't stop thinking about: organizational slack. Not the chat app. The breathing room that separates a team that can think, create, and adapt from one that's just grinding toward collapse. We get into why micromanagement is usually fear dressed up as accountability, the difference between being a manager and actually leading a team, and what Rasmussen's Drift model tells us about what happens when there's no buffer left in the system. We also talk motivation — why assuming your team is driven by the same things you are is one of the most common and costly mistakes a leader makes. Plus: the case for being delusional, and why being a slacker might be the most underrated leadership skill of our time.

May 27, 2026Episode 336 min

Why Can't We Talk to Each Other?

Learning to Disagree Without Being Disagreeable Every leader has said it: "I have an open door. Bring me your concerns." And then... nothing. No one comes. And yet somehow everybody's talking to everybody except the person they actually have an issue with. In this episode, I sit down with Danielle Loevy a mediator, executive coach, and former employment lawyer. We dig into why disagreement is a skill most of us prefer not to engage, why calling yourself "conflict avoidant" is a limiting label, and what's really happening when your team won't just talk to each other. Plus, she provides four pillars for actually getting good at disagreement. And yes, a foster dog makes a cameo.

May 13, 2026Episode 215 min

Are Unwritten Rules Running Your Team?

Have you ever watched a murmuration of starlings? Thousands of birds, no leader, no plan — moving like one organism. That's not magic. That's emergence. And it's exactly what's happening on your team, whether you're paying attention or not. This episode is about the invisible architecture of teams — the dynamics that form whether you design them or not. I walk through three layers of how team behavior actually develops, pull from Adrienne Maree Brown's Emergent Strategy, and revisit Kurt Lewin's counterintuitive finding: it's easier to change a group than to change an individual. I tell two stories that made this real for me. The first: I went to a retreat, had a genuine transformation, came home — and my environment hadn't changed. The environment won. The second: I sat on a board where the defining norm was harmony. Don't disagree with the inner circle. I abstained from one vote. That was enough to break it. Norms aren't rules. Nobody writes them down. But they run everything.

May 6, 2026Episode 118 min

Is Your Team An Actual Team?

Most of us have been on teams our whole lives — sports teams, school projects, work groups — and still have no idea what a team actually is. Spoiler: most of what we call "teams" aren't. In this episode, I'm breaking down the difference between a working group and a real team, why interdependence is the thing that changes everything, and what researchers like Richard Hackman and Amy Edmondson actually mean when they talk about "teaming." It's more useful — and more unsettling — than the motivational poster version. I also get honest about something personal: I grew up on sports teams and was sometimes a genuinely terrible teammate. Not because I didn't care — because I cared too much about the wrong things. If you've ever wondered why some groups click and others just... coexist — this one's for you Connect: https://www.linkedin.com/in/jessy-grossman/ @coachjessygrossman zlncoaching.com

December 17, 2025Episode 1034 min

What Does It Really Mean to Live With Clarity?

In this episode, Jessy Grossman and Amanda Hoffmann dive deep into the meaning of clarity — not as certainty or perfection, but as an ongoing practice of understanding, alignment, and curiosity. Amanda shares her Core Alignment Model, a framework designed to help people reconnect with their identity, values, and aspirations—and to interrupt the growing epidemic of the borrowed self : the version of ourselves we adopt from others' expectations. Rich, reflective, and refreshingly honest, this conversation will help you pause, notice, and reconnect. Learn more about Amanda Hoffmann's work: https://www.linkedin.com/in/arhoffmann/

December 3, 2025Episode 938 min

What Corporate Leaders Can Learn From DAOs and Decentralized Leadership?

In this conversation, Katerina and Jessy explore the shiny, new ideas shaping the future of organizations—namely decentralization, democratized decision-making, and transparent information flow . Drawing on Katerina’s experience working inside emerging organizational structures and teaching on new technologies, they translate concepts from Web3, DAOs, and network-based leadership into practical lessons for leaders working in traditional companies today . Together, they unpack why information sharing is becoming one of the most critical leadership skills, the strengths and limits of decentralized structures, and what corporate America can adopt (without needing a blockchain or token system). The conversation highlights the evolving role of leaders—not as answer-givers, but as connection-builders who create the conditions for people to collaborate, communicate, and make better decisions together . As more organizations operate in complex, fast-changing environments, leaders are increasingly expected to orchestrate networks , not manage silos. This episode bridges the world of emerging organizational tech with real-world leadership challenges—and gives listeners practical ways to experiment with decentralized principles in their own teams.Learn more about Katerina: https://www.linkedin.com/in/katerinabc/

November 19, 2025Episode 842 min

How Your Story Shapes Your Leadership w/ Dan P. McAdams

What story are you telling about who you are—and who you’re becoming? In this episode, Jessy Grossman sits down with Professor Dan P. McAdams, one of the world’s leading experts and field-defining scholars on narrative identity and personality development. Professor McAdams — the Henry Wade Rogers Professor at Northwestern University — has spent his career studying how we weave our experiences into stories that give our lives coherence, meaning, and purpose. Together, they explore how the stories we tell about ourselves shape the way we lead, adapt, and ultimately leave a legacy — especially during times of uncertainty and change. If you enjoy this episode, don’t forget to subscribe to Too Millennial and leave a review — it helps us reach more leaders like you! Learn more about Dan McAdams’ work on narrative identity: https://sites.northwestern.edu/studyoflivesresearchgroup/

November 5, 2025Episode 739 min

Harnessing AI: Fast-Tracking Change

Join Karrie Sullivan , founder of Culminate Strategy Group , as she delves into the intricacies of AI adoption and organizational transformation . In this conversation, we explore why understanding the human element is key to successful change — and how leaders can meet people where they are, shift mindsets, and show up with confidence through uncertainty. Let’s stay connected! Follow me on Instagram @CoachJessyGrossman for leadership insights, behind-the-scenes stories, and tools to help you grow as a leader. Connect with me on LinkedIn , and connect with Karrie Sullivan to continue the conversation on AI adoption and organizational transformation.