Too Millennial: Unleashing the Next Generation of Leaders

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....

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 roadm...

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 fro...

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 disagr...

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 lay...

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...

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 o...

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 le...

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 int...

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 Instag...

How improv Skills Can Make You a Better Leader (Even If You're Not That Funny) Megan Redfearn unpacks the surprising links between improv, teams & leadership. In this hilarious and insightful conversation, Megan Redfearn joins Jessy Grossman to explore the unexpected but powerful intersection of improv and leadership. Together, they unpack how the core principles of improv—like “yes, and”, lis...

Understanding the Difference Between Leadership and ManagementIn this mini solo episode, we unpack one of the most overused (and misunderstood) buzzwords in the workplace: leadership. You’ve seen it splashed across LinkedIn with sunrise photos and TED Talk quotes… but what actually is leadership? And how is it different from management? In This Episode, We Explore:- 4 minute mark: The classic Mana...

From Strategy to Results In this episode, Jessica Grossman sits down with consultant Julian Chender to explore the nuances of organization design—what it is, how it works, and why it matters more than ever in times of disruption. Together, they unpack why new strategies require new designs - not just new org charts. In this conversation, you'll learn: Why aligning design with strategy is criti...

Whether you’re a healthcare provider, a leader managing high-pressure teams, or someone passionate about systems change, this episode is a must-listen. In this episode of Too Millennial: Unleashing Leadership for the Next Generation , host Jessy Grossman sits down with Dr. Tricia James, MD to explore the mental health crisis in medicine and the cultural myths that fuel burnout. Dr. Tricia shares h...

In this episode, Jessy sits down with Christina Cheuk—positive psychologist, CEO of Two Happy, and Assistant Professor at University of Pennsylvania, where she teaches under the legendary Marty Seligman. Together they explore a powerful shift in how we think about leadership, well-being, and what really fuels us: mattering. Together, they unpack why purpose alone isn’t enough—and why our sense of...

In this episode, Jessy Grossman gets personal about the question: “Am I too disruptive?” She explores the evolving concept of disruptive leadership , sharing how the courage to challenge the status quo can be both a strength and a struggle. Through the lens of her own experiences as a disruptor, Jessy unpacks how effective leaders can channel disruption into positive transformation. This episode i...

Join Jessy Grossman and Sarah Malone as they explore Appreciative Leadership, a strengths-based approach to leadership and organizational development. Discover how recognizing individual strengths, fostering respectful communication, and building a positive culture can transform teams. This episode highlights the transformative impact of Appreciative Leadership and the crucial role mindset plays i...

Women Ascend In this conversation, host Jessy is joined by Yara and Margaret to understand the multifaceted landscape of women’s leadership. Together, they unpack the unique trends, challenges and opportunities women encounter in the workplace, emphasizing the importance of intersectionality and community support in driving meaningful change. The conversation sheds light on societal expectations,...

Time Flow, Cash Flow & Team Flow for Optimal Performance? Join host Jessica Grossman as she sits down with Dr. Orin Davis to explore the nuances of team dynamics, the art of deliberate "team building," and the challenges of fostering true inclusion within teams. Dr. Davis introduces the concept of "team flow" and discusses its pivotal role in achieving peak team performance. Together, Grossman...

In this insightful conversation, Jessy Grossman and Allie Stark delve into the critical aspects of leadership coaching and the interplay between the inner and outer game of leadership. They discuss how self-awareness, self-regulation, and the process of unlearning are vital for effective leadership development. Additionally, they emphasize the importance of resilience—not just as a personal trait...

In this episode, Jessy Grossman welcomes Libby Rodney , Chief Strategy Officer at The Harris Poll and futurist, to discuss the latest cultural and workplace trends impacting Millennial leaders . They explore topics such as quiet vacationing , the effects of layoffs on employee engagement and innovation , and the vital role of vulnerability in both parenting and leadership . This episode provides a...

The Power of Manifestation? Moving from Chaos to Clarity In this enlightening conversation, Jessy and Nicole dive deep into the concepts of manifestation and intention setting, exploring how these practices can shape leadership's vision and purpose. At the ~20-minute mark Nicole leads listeners through a guided practice designed to help them experience manifestation and intention setting firsthand...

In this episode of Too Millennial , host Jessy Grossman interviews communications expert and CEO of Career Civility, Jenna Rogers, to explore the evolving role of email in workplace communication and strategies for mastering it. They dive into the challenges of writing impactful emails, navigating power dynamics, and the lack of formal training in email communication. Jenna shares practical tips o...

Belonging, Ego & High Performing Teams In this thought-provoking episode, Jessy Grossman and Ashly Williams discuss the intricate dynamics of ego, competition, and fear in the workplace, shedding light on how these elements perpetuate toxic environments. Ashly Williams shares poignant anecdotes highlighting the systemic disparities and racism prevalent in many workplaces, emphasizing the urgen...

Leadership that Unlocks Peak Performance  In this episode, host Jessy Grossman interviews Brian Gelber, a successful trader, visionary leader and Co-Founder of the proprietary trading firm Gelber Group. Gelber emphasizes that to achieve higher performance, one must cultivate self-awareness and prioritize well-being. This episode dives into Brian Gelber's journey, from being a successful trader...