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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