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

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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 practice

DOWNLOAD THE PLAYBOOK: https://thejolt.myflodesk.com/disruptiveleadership

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Website: https://www.zlncoaching.com
Instagram: @coachjessygrossman
LinkedIn: Jessy Grossman

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.