Too Millennial: Unleashing the Next Generation of Leaders – Details, episodes & analysis

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Too Millennial: Unleashing the Next Generation of Leaders

Jessy Grossman

Business

Frequency: 1 episode/27d. Total Eps: 24

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 Fueled by frustration with outdated work norms and clients on the edge of burnout, she's left with a desire for a better way.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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🇨🇦 Canada - management
15/04/2026
#67

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https://www.linkedin.com/in/jessy-grossman/
3 shares
https://www.linkedin.com/in/christina-cheuk/
2 shares
https://www.linkedin.com/in/jessygrossman
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Score global : 68%

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What Does It Really Mean to Live With Clarity?

Season 2 · Episode 10

Wednesday, December 17, 2025 • Duration 34:19

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/

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What Corporate Leaders Can Learn From DAOs and Decentralized Leadership?

Season 2 · Episode 9

Wednesday, December 3, 2025 • Duration 38:23

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/

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Appreciative Leadership: A New Paradigm for Effective Leadership

Season 1 · Episode 13

Wednesday, December 18, 2024 • Duration 36:39

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

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Women Ascend: Leadership Trends and Challenges Ahead

Season 1 · Episode 12

Wednesday, December 4, 2024 • Duration 45:49

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:

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

Finding Flow with Dr. Orin Davis

Season 1 · Episode 11

Wednesday, November 13, 2024 • Duration 57:41

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)

Coaching for Resilience: The Inside and Outside Game of Leadership

Season 1 · Episode 10

Wednesday, October 30, 2024 • Duration 52:23

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

Millennial Leadership Trends: Parenting, Quiet Vacationing & Workplace Evolution w/ Libby Rodney

Season 1 · Episode 9

Wednesday, October 16, 2024 • Duration 49:41

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/

Moving from Chaos to Clarity: Using the Power of Manifestation?

Season 1 · Episode 8

Wednesday, October 2, 2024 • Duration 31:21

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/

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Workplace Communication: Email Best Practices and Team Norms

Season 1 · Episode 7

Wednesday, September 18, 2024 • Duration 57:17

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

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Feeling Special: Belonging, Ego & High Performing Teams

Season 1 · Episode 6

Wednesday, May 29, 2024 • Duration 49:12

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

Too Millennial: Unleashing the Next Generation of Leaders – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

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Too Millennial: Unleashing the Next Generation of Leaders – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other25

LinkedIn6

Amazon5

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other25

LinkedIn6

Amazon5