Too Millennial: Unleashing the Next Generation of Leaders

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/

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/

From Strategy to ResultsIn 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 resultsThe difference between structure and design—and why it mattersWhat leaders often get wrong when trying to “break down silos”Why people shouldn’t be the first consideration in org designHow to spot signals that your current design no longer fits your strategyJulian reminds us: There’s no one-size-fits-all in organizational design. It’s about building the muscles necessary for sustainable strategy execution.Love the Show? Share it with a friend, rate & review and tag us with your favorite moment!

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-beingReferences: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 ChristinaWebsite: twohappy.orgLinkedIn: https://www.linkedin.com/in/christina-cheuk/Connect with JessyWebsite: https://www.zlncoaching.comInstagram: @coachjessygrossmanLinkedinLove the Show? Share it with a friend, rate & review and tag us with your favorite moment!

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 invites listeners to rethink disruption—not as reckless upheaval, but as intentional, values-driven leadership in service of innovation, inclusion, and progress—the desire to build something better.✨ Bonus: Stay for the surprise guest at the end!Key Takeaways:Disruptive leadership begins with self-disruption.Effective leaders consistently challenge their own assumptions.Disruption is uncomfortable—but essential—for growth.Disruptive leaders intentionally replace unsatisfactory status quos.Disruptive leadership is not a moment—it’s a lifelong practiceDOWNLOAD THE PLAYBOOK: https://thejolt.myflodesk.com/disruptiveleadershipLove the Show? Share it with a friend, rate & review on Apple Podcasts or Spotify, and tag us with your favorite moment!Website: https://www.zlncoaching.comInstagram: @coachjessygrossmanLinkedIn: 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.

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 in effective leadership. Perfect for leaders who aim to inspire and connect rather than direct and enforce. Takeaways: What is Appreciative Leadership? Why is Appreciative Leadership important? What Appreciative Leadership is not How to get started with Appreciative Leadership Don’t forget to sign up for Women Ascend Leadership Cohorts starting in January here: https://thejolt.myflodesk.com/womenleadership

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, generational differences, and self-limiting beliefs that often shape women’s leadership journeys. Jessy, Yara & Margaret also discuss low performers, people-pleasing tendencies, and addressing workplace friction to cultivate a more equitable environment for women leaders. DOWNLOAD THE BROCHURE: 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, generational differences, and self-limiting beliefs that often shape women’s leadership journeys. Jessy, Yara & Margaret also discuss low performers, people-pleasing tendencies, and addressing workplace friction to cultivate a more equitable environment for women leaders. DOWNLOAD THE BROCHURE: https://thejolt.myflodesk.com/ascendleadership Takeaways Women often take on dead-end work that doesn't lead to promotion Societal expectations uniquely shape women’s approaches to leadership Intersectionality is crucial in understanding women's experiences in leadership Friction in the workplace can be nuanced and hidden Generational differences change the perception of gender bias Feedback for women disproportionately focuses on personality traits rather than performance outcomes Confidence is built through action

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 and Davis delve into essential topics like effective team onboarding, purposeful team formation, and the value of returning to first principles. They stress the importance of bridging theory and practice in today’s workplace, helping organizations navigate key tradeoffs—especially around time. Key Topics Covered: What is positive psychology? The complexity of team inclusion and what it takes to foster it. Understanding "team flow" and the steps to achieve it. The critical role of team formation and onboarding. Balancing priorities and managing time tradeoffs within teams and organizations. How academia has evolved and the impact of scientists and consultants not collaborating. Why organizations should invest in the R&D of organizational development. Orin Davis Website Jessy Grossman Website Key References: Orin Davis' TedTalk How to Spark Team Flow Over Time (Team Flow Paper discussed in the interview) Jessy’s Team Model & Playbook Team Flow Overview (Youtube) Flow: The Psychology of Optimal Experience by Mihaly Csikszentmihalyi  Team Flow: The psychology of optimal collaboration by Jef J.J. van den Hout & Orin C. Davis  Positivity 101: 15 Science-Based Strategies for Cultivating Enjoyment, Gratitude, Serenity, and Awe by Barbara Fredrickson 

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 but as a product of supportive systems and environments. Key Topics Covered: The Inside and Outside Game of Leadership: Understanding the balance between personal growth and external leadership effectiveness. The Role of Self-Awareness & Unlearning: How being attuned to one’s emotions and motivations can enhance leadership capabilities. The importance of letting go of outdated beliefs and practices to foster growth. Resilience in Leadership: Redefining resilience as the ability to adapt meaningfully rather than merely enduring adversity, and recognizing the importance of social support in fostering resilience. Generational Communication: The need for effective communication strategies across different age groups within teams. Coaching vs. Therapy: Exploring the distinctions between coaching and therapeutic practices, and how vulnerability plays a role in coaching relationships. Creating a Culture of Well-Being: Allie shares practical insights on how to foster an environment that supports team members and prevents burnout. Join the Conversation:What are your thoughts on the role of coaching in leadership? Share your insights and experiences with us on social media! Follow Allie StarkInstagram: allie_stark_wellness Website: https://hellonoria.com/ Follow Jessy Grossman:Instagram: @CoachJessyGrossmanWebsite:zlncoaching.com Guest: Allie Stark is a a leadership coach, facilitator, and founder of Allie Stark Wellness—a powerhouse team of five coaches—and co-founder of Noria, a platform redefining modern living and leading. Allie guides entrepreneurs and leaders to launch impactful organizations, trains coaches in her unique methodology, and leads workshops for some of the world’s biggest brands.

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 actionable strategies and data-driven insights to help you navigate today’s evolving work landscape and prepare you for the current workplace evolution. Key Topics Discussed: Vulnerability in parenting and leadership The U.S. Surgeon General's warning on mental health for parents The concept of quiet vacationing and the fear of asking for rest The impact of layoffs on employee engagement and innovation The interplay between identity and work The importance of setting clear expectations Strategies to overcome feelings of "not enough" Connect with Libby SubStack: The Next Big Think Website: https://libbyrodney.com/ Connect with Jessy Instagram: @coachjessygrossman Website: https://www.zlncoaching.com/

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, fostering clarity, strength and alignment.  This isn't the episode you think you need as a leader, but it's the episode you never knew you were missing! How? It will ground you amidst the busyness, help you reconnect with your vision, and create a source of resilience. Connect with Nicole Website: https://www.nicolebelica.com/ Instagram: @nicolebelica Don’t forget to subscribe to the podcast and leave a review! Your feedback helps us continue to bring you valuable insights on leadership, manifestation, and growth. Other resources: https://freakonomics.com/podcast/can-you-really-manifest-success-through-positive-visualization/

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 on establishing clear communication norms, leveraging technology to improve communication, and how civil communication fosters a collaborative, inclusive work environment. This episode provides actionable insights for leaders and professionals seeking to improve workplace communication and productivity. Key Topics Discussed: Power Dynamics in Communication: Strategies for navigating authority and influence when crafting professional emails. Civil Communication: The importance of shared understanding and mutual respect in productive workplace interactions. Team Dynamics & Norms: How clear, inclusive communication contributes to building effective teams. Connect with Jenna Rogers: Website: https://www.careercivility.com/ Instagram: @CareerCivility Topics we explore: email writing strategies, psychological safety, team dynamics, generational communication differences, leadership, inclusive communication, professional communication tools, high-performing teams

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 urgent need to create a sense of belonging. They stress the importance of cultivating a culture of psychological safety, where everyone's contributions are valued, and authenticity is celebrated. The episode also addresses the critical role of diversity, equity, inclusion, and belonging (DEIB) in dismantling negative workplace dynamics. Grossman and Williams dissect how using DEIB as coded language often perpetuates division and defensiveness, hindering progress to true belonging. To initiate change, Ashly Williams advocates for building a culture of feedback and fostering a growth mindset as essential steps toward achieving these goals. Tune in to be enlightened on all things ego, belonging, and psychological safety to build a better future. Key Topics: - Impact on competitive environments & teamwork - Backlash to Diversity, Equity, Inclusion, Belonging (DEIB) - Creating a Culture of Belonging & Psychological Safety - Impact of effectively giving and receiving feedback - Adopting a Learning Mindset - Reimagining Work - Belonging and Organizational Performance - Fostering Belonging in Organizations Want to start giving effective feedback?  You can find the scripts here: https://thejolt.myflodesk.com/feedback Support the Podcast by: Subscribe/follow button & share it with your squad Tell me how special I am in the comments  Follow me on Instagram @coachjessygrossman

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 to leading Gelber Group, and the lessons Gelber learned along the way. Brian Gelber shares personal stories of failure, decision making and resilience, highlighting the importance of learning from setbacks. Gelber also discusses his leadership style and the value of creating a supportive and empowering culture. The episode concludes with host Jessy introducing the SOAR framework, which emphasizes strength, optimization, agility, and resonance in achieving sustainable high performance. Download the SOAR visual! https://thejolt.myflodesk.com/soartoperform  Key Topics:  - The importance of balancing high performance and well-being  - Brian Gelber's reflections on his enduring legacy from the interview in "Market Wizards.  - Gelbers perspective on handling setbacks and learning from failures - An anecdote about a significant trading loss and the lessons learned from it. - The importance of poise and making the right decisions under pressure. - The distinction between traditional learning and experiential learning. - Brian Gelber's natural leadership tendencies and how they've evolved. - The importance of listening and adapting leadership styles to different generations. - Gelber Group's culture of opportunity & the importance of allowing employees to make mistakes and learn from them. - The characteristics of millennial leaders Don't miss an episode! Subscribe to Too Millennial on your favorite podcast platform. If you enjoyed this episode, please leave a review and share it with your friends! Resources: Schwager, J. D. (1989). Broker turned trader: Brian Gelber. In Market Wizards: Interviews with Top Traders (pp. 325-341). New York, NY: New York Institute of Finance. Gelber Group: https://www.gelbergroup.com/

Exploring the Interplay of Mind and Body for Wellbeing In this conversation, Jessy interviews Nicole Belica, a yoga teacher and mindfulness coach, about the importance of embodiment and its role in leadership. They discuss how embodied leadership allows us to be present in the moment and respond to stressors in a healthy way.  Nicole shares practical tips for cultivating embodied leadership, such as deep breathing and paying attention to physical sensations. They also explore the challenges faced by leaders who are caught between managing expectations from above and supporting their team members. The conversation concludes with a 12 min guided movement practice led by Nicole. Feel free to move with this audio only option – listening and flowing to the cues.  But if you want more visual cues, you can find the guided movement here: https://youtu.be/XFNWJvlSqIo Key Topics for Embodied Leadership Embodiment and its Importance Impact of Dissociation Key Aspects of Embodied Leadership Practical Tips for Embodiment Understanding & Managing Stress as a Leader 12 min Guided Movement from 26 - 38 min mark References: Gross, J. J. (1998). The emerging field of emotion regulation: An integrative review. Review of General Psychology, 2(3), 271-299. https://coachingfederation.org/blog/cultivating-embodied-leadership