Too Millennial: Unleashing the Next Generation of Leaders

Hosted by Jessy Grossman

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Oct 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 Fueled by frustration with outdated work norms and clients on the edge of burnout, she's left with a desire for a better way.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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33 recent

October 21, 2026Episode 935 min

Are Teams Joyful or Anxiety-Inducing?

Superstars and the Epicenter Test with Debbie Plager Two team effectiveness practitioners who see teams in opposite ways share what they learned from teaching Northwestern undergrads, and what leaders can do about it.I'm joined by my mentor and co-teacher Debbie Plager, founder of Lumin Partners, to talk about why teams energize some people and stress others out, why a team of all superstars doesn't work (yes, there's a super chicken story), and one test you can run in your very next team meeting to find out whether everything on your team runs through you. Resources mentioned “Why it’s time to forget the pecking order at work” (the super chicken TED Talk), Margaret Heffernan, TED 2015 Thomas-Kilmann Conflict Mode Instrument The Prism assessment: https://www.surepeople.com/prism Connect with Jessy LinkedIn: https://www.linkedin.com/in/jessy-grossman/ Website: https://www.zlncoaching.com Connect with Debbie Lumin Partners: https://lumin-partners.com/

October 7, 2026Episode 836 min

What Foster Dogs Teach Us About Leading Teams with Heather Owen

I coach teams. I foster dogs. And lately, I can't tell which one is teaching me more. So today, I'm merging my two worlds by sitting down with Heather Owen, co-founder of One Tail at a Time, to talk about what dog packs teach us about leading teams: the correction we never make, the repair we always skip, and why the healthiest teams aren't the ones without conflict but the ones that know how to recover from it. Stay tuned for the story of a 100-pound dog, an 18-pound grumpy senior, and months of tolerating it, until one day he didn't. Want to help? As Heather says, the best thing you can do for animals is something . Donate to a local rescue. Volunteer at your shelter. Foster, which is how I started, and it's the number one way rescues can save more animals. Or adopt your next dog or cat. If you're in Chicago, start with One Tail at a Time: https://www.onetail.org/ Fair warning: once you start, you may find yourself refreshing the adoption page every weekend to see who found their home. Ask me how I know.

September 23, 2026Episode 733 min

From 5 Centers to 25: Lessons in Scaling Your Executive Team

Stride has grown from five centers to twenty-three, with a twenty-fifth opening soon. Founder & CEO Brad Zelinger joins Too Millennial to talk about what it actually took to build a leadership team that could carry that growth — retooling recruiting from gut-feel to structured competency evaluation, the hard lesson of repositioning loyal people into roles that didn't fit, the shift from hands-on execution to managing managers, and how Stride became data-driven without losing the caring, mission-first culture it was built on. If Episode 1 was about what makes a team a team, this is what building one actually looks like in the real world. Takeaways: structured recruitment → better team fit · role repositioning is riskier than it looks · leadership needs change at every stage of scale · data and KPIs matter, but aggregate numbers can hide real problems · culture survives on intentional, repeated effort — not good intentions.

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/