Jacob Rooksby was the youngest law dean in the U.S. when he was appointed in 2018 to lead the Gonzaga University School of Law. Eight years later, his leadership journey is taking him to a new role, as dean of the University of Richmond School of Law.

Our conversation with Jacob covered many of the ways in which higher education offers distinctive leadership challenges and opportunities. Jacob also talked about what he learned about leading and what he learned about himself during his tenure at Gonzaga, including a shift in focus from "leading as decision-making" to "leading people to their own source of power."

He reflected on many of the human elements of leadership, including the importance of modeling the behavior that a leader hopes to see in others, the roles of keeping an open heart as well as an open mind, and the challenges of loneliness in the leader's seat.

In all, this episode again confirms the core message of Your Leadership Podcast: context makes all the difference.

Find Jacob:

LinkedIn

Jacob Rooksby's website

The University of Richmond School of Law

What makes Your Leadership Podcast different? Our co-hosts Kathy Edersheim and Michael Madison and our guests are down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us at yourleadership.net!

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Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

You Mon Tsang leads as an entrepreneur. Today, he is the CEO of ChurnZero, an AI-powered software platform for customer success – his fifth startup overall.

This interview with You Mon covers his path from “employee”to “leader,” anchoring his journey in his “lead dog” identity. Your Leadership Podcast consistently emphasizesleading and leadership in context, and You Mon’s private sector experience and success captures that sensibility perfectly.

Find You Mon:

LinkedIn

You Mon on entrepreneurship, at CHURN.FM

ChurnZero

What makes Your Leadership Podcast different? Our co-hosts Kathy Edersheim and Mike Madison and our guests are down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us at yourleadership.net!

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Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

Ken Inadomi has been a leader in both private sector and nonprofit organizations, and he has spent decades honing his vision and practice through reflection in a journal, now published in book form.

This interview with Ken includes both the sweep of his leadership experience and vision and also concrete examples and illustrations from the different stages of his leadership career. The product is a usable template for a life in leadership, tailored - as Ken has done - to the person and the context.

Find Ken:

LinkedIn

keninadomi.com

Book: The Pen & the Mirror: Wisdom from 50 Years of Journaling (2026)

Yale Alumni Nonprofit Alliance (YANA)

Project Redwood

What makes Your Leadership Podcast different? Ourco-hosts Kathy Edersheim and Mike Madison and our guestsare down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us at yourleadership.net!

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Your Leadership Podcast is produced and engineered byCommander Buffalo.

While the Commander may use AI to help us organize ourinterviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

Andrew Frishman is the co-Executive Director of BigPicture Learning, a nonprofit organization that is at the forefront of innovation in education, building a network of schools that put students rather than standardization at the center of learning.

This interview with Andrew features a wide ranging tour of leadership practices that Andrew and Big Picture follow, from servant leadership to leading without formal authority, building in “productive conflict,” and understanding leadership in systems – and systems of systems. Andrew wraps up the package with reflections on “leadership jazz.”

What makes Your Leadership Podcast different? Our co-hosts Kathy Edersheim and Mike Madison and our guests are down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us at yourleadership.net!

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Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

Your Leadership Podcast returns for Season 3 with this introduction that surveys key themes and topics to come.

Co-hosts Kathy Edersheim⁠ and ⁠Mike Madison kick off this two-handed episode by picking up where Season 2 left off - there is no one-size fits all leadership strategy; there is only context - and detailing some critical elements of that observation as prompts for this season's interviews:

How should leadership strategies and tactics differ between in-person settings and online or virtual settings? How should leadership thinking shift when leaders and organizations move from "build it" phases to "sustain it" or "evolve it" phases?

And what about Generative AI?

What makes Your Leadership Podcast different? Our co-hosts and our guests are down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us!

⁠Find us on LinkedIn. ⁠

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Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

Your Leadership Podcast returns for Season 3!

In this brief intro, co-hosts Kathy Edersheim and Mike Madison preview episodes and guests to come.

We will highlight overlaps and intersections among key leadership challenges and transforming technologies and practices: Generative AI in the workplace, in the home, and in all the places, spaces, and groups that define contemporary life. Creating and building as leadership goals contrasted with leadership in sustaining, continuing, and evolving organizations. And leadership in "classic" face-to-face settings distinguished from leadership in remote and virtual environments.

What makes Your Leadership Podcast different? Our co-hosts and our guests are down in the trenches, learning and leading by doing, in a broad variety of contexts, and generating leadership takeaways useful for experienced and aspiring leaders alike.

Join us!

Find us on LinkedIn.

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Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

In this finale for Season 2 of Your Leadership Podcast, co-hosts Kathy Edersheim and Michael Madison take stock of the season's interviews and guests:

What did we hear that confirmed our intuitions?

What did we hear that surprised or challenged us?

And most important, what do we take away and recommend to our listeners?

Your Leadership Podcast is about actionable insights. We've tied Season 2 together with a bow to make it useful ... to you.

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About us:

Find Your Leadership Podcast online at yourleadership.net, and use that site to send in questions and comments.

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Production notes:

Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.

Sean Casey, a retired American professional baseball player, is known as “The Mayor” for his personable demeanor both on and off the field. He was selected as an All-Star, played in the World Series, and finished a decade-long career as a .300 hitter – a sign of his talent and his consistency. Since retiring from the field, Sean has continued in baseball as a media personality. And he has put time and effort into community service.

In this conversation with co-hosts Mike Madison and Kathy Edersheim, Sean digs into his past and present experiences to explain how he acquired, practiced, and paid forward the discipline and commitment that leadership meant for him, and still means today, in all aspects of his life and career.

Sean Casey on X: @TheMayorsOffice

SeanCasey on Instagram: @themayorsofficemlb

Sean Casey’s keynoting

Sean Casey’s volunteering and service: “Casey’s Clubhouse”

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About us:

Find Your Leadership Podcast online at yourleadership.net, and use that site to send in questions and comments.

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Production notes:

Your Leadership Podcast is produced and engineered by Commander Buffalo.

While the Commander may use AI to help us organize our interviews, our podcast features only human voices, and our musical accompaniment is composed and performed by the very human Matt Madison.