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/

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/

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.

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”, listening deeply, and being present—can dramatically enhance leadership skills, foster psychological safety, and build stronger team cultures. From quirky jokes to grounded leadership wisdom, this episode highlights how improv can be a game-changing approach to collaboration, coaching, and performance.

• Improv builds leadership muscles. It helps develop quick thinking, collaboration, and emotional intelligence.
• “Yes, and” is a leadership superpower. It fosters psychological safety, curiosity, and forward momentum.
• Divergence is necessary. Great teams need different perspectives and healthy tension to innovate and grow.
• Listening is a leadership skill. Improv teaches how to truly hear others and respond with presence.
• Coaching and improv overlap. Both require curiosity, co-creation, and letting go of control.

Connect with Jessy- Website: https://www.zlncoaching.com- Instagram: @coachjessygrossman - LinkedIn: https://www.linkedin.com/in/jessy-grossman/

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 Managers vs. Leaders debate- 8 min mark: What scholars and thought leaders — from Simon Sinek to Warren Bennis to Peter Senge — say about leadershipMentioned in This Episode:- Simon Sinek quoting Bob Chapman- Warren Bennis- Peter Senge – The Fifth Discipline- Doc Norton quote from Forbes- Ekiru, F. A. (2025). *Effect of Leadership and Management Inefficiencies on Employee Motivation and Engagement in Community-Based Organizations in Turkana, Kenya*. IRASS Journal of Arts, Humanities and Social Sciences, 2(5), 11–18.And if you enjoyed this episode, share it with someone who leads with heart — or is learning how to.

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 critical to achieving results

• The difference between structure and design—and why it matters

• What leaders often get wrong when trying to “break down silos”

• Why people shouldn’t be the first consideration in org design

• How to spot signals that your current design no longer fits your strategy

Julian reminds us: There’s no one-size-fits-all in organizational design. It’s about building the muscles necessary for sustainable strategy execution.

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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 her personal journey through medical training and the moment she realized the system was breaking her.

Together, they challenge the belief that excellence requires self-sacrifice and explore how leadership, coaching, and community can create a healthier future.

From team dynamics and time pressures to the power of reflection and small wins, this is a reality check for anyone who leads, whether you’re in healthcare or not.

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 impact and being seen matters.

Key Reminders:

🌱Mattering = feeling valued and adding value

🌱 Thriving is complex—it’s not just about being happy

🌱Purpose = long-term goals and mission (not just answering a “calling”)

🌱 You need both purpose and mattering for true well-being

References:Steger, M. F. (2012). Making meaning in life. In P. T. P. Wong (Ed.), The human quest for meaning: Theories, research, and applications (2nd ed., pp. 165–184). Routledge.

Prilleltensky, I., & Prilleltensky, O. (2021). How people matter: Why it affects health, happiness, love, work, and society. Cambridge University Press.

Connect with Christina

• Website: twohappy.org
• LinkedIn: https://www.linkedin.com/in/christina-cheuk/

Connect with Jessy

• Website: https://www.zlncoaching.com
• Instagram: @coachjessygrossman
• Linkedin

Love the Show? Share it with a friend, rate & review and tag us with your favorite moment!