Leading Organizations That Matter
A weekly podcast covering topics of interest for those who lead, support, or simply care about "organizations that matter". These include mission driven, nonprofit health care and social service organizations that exist in order to improve the lives of those who experience great challenges. Profitability is obviously important... but so too is the recognition of the other forms of value generated in these settings. Podcast topics include how we finding meaning, purpose, and impact in our work, organizational culture, leadership challenges, changing the trajectory of struggling organizations, and practical leadership strategies. Episodes are brief and to the point, always with the goals of informing and elevating listeners. Occasionally, I interview leaders and experts in related fields and hope to bring you inspiration and information to facilitate your personal leadership and life journey. For more information, please see RedSailAdvisors.com.
Music by Kevin MacLeod at incompetech.com.
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Episodes
110 episodes
109. Here’s to the Pitchers
Are you the pitcher… or the catcher?In this episode of Leading Organizations That Matter, I share a simple lesson from a 1990s golf pro that reshaped how I think about leadership.
108. My Brother Tricked Me and Why You Should Care
In this episode of Leading Organizations That Matter, I dive into the strange, fascinating rise of Eddie Dalton — the soulful, chart‑topping singer.Here, I explore why Eddie’s success leaves us feeling both outraged and...
107. Why You Need to Write
What if the clearest way to think isn’t in your head at all... but on the page? In this episode, I explore why writing isn’t just a creative act, but a leadership discipline. Drawing on Flannery O’Connor, the rise of AI‑generated text, and my o...
106. Seeing the Forest AND the Trees
What if the way you see the world is shaping the way you lead - without you even realizing it? In this episode, I draw on a surprising source - photography - to explore why some leaders naturally zoom out to the big picture while others instinc...
105. Renee McInnes: Passion for the Mission
What does it take to lead a mission‑driven health care organization with clarity and heart? In this episode, I sit down with Renee McInnes, CEO of Croí Health, to talk about purpose, culture, and the real work of caring for both patients and th...
104. Maureen Groden: When a Loved One Is Dying
What does it mean to truly accompany someone at the end of life? In this episode, I sit down with Maureen Groden, author of When a Loved One Is Dying, to explore the wisdom, clarity, and compassion she offers to families navigating one...
103. I Wish That I Was More Data Driven
What if being “data driven” isn’t actually about the data at all? This week, I unpack a deceptively simple confession from a client and reveal the two hidden skills every leader needs - but most never develop. One is about understanding the das...
102. Look at the Portfolio!
What can a photography workshop teach us about leadership? More than you’d think. This episode breaks down why a strong portfolio matters, how to separate real expertise from polished marketing, and what every leader should look for when select...
101. Do We Have a Toxic Positivity Problem?
We all love positivity - but what happens when it becomes performative, relentless, or downright harmful? In this episode, I dig into the rise of toxic positivity, why it’s everywhere online, and how it can leave us feeling more disconnected an...
100. My War on Dis-Integration
This milestone episode explores what happens when the roles we play become so separate that we start to feel divided from ourselves. Drawing on a candid personal story and a powerful coaching conversation, it looks at how compartmentalization c...
99. I Want to Become More Strategic
So many leaders say, “I want to be more strategic”—but what does that really mean? In this episode of Leading Organizations That Matter, I break down the myths and offer four practical ways to sharpen your strategic thinking a...
98. I Don’t Hate AI, But…
In this week's episode, I take on the AI revolution with a candid confession: I use the tools - but refuse to let them write for me. In this episode, I describe the moment I realized that I was standing at the edge of a creative waterfall, the ...
97. Starting Season 3: About This Podcast
A milestone episode kicks off Season 3 as I pull back the curtain on what nearly 100 episodes have revealed about what listeners truly crave: honest reflections on leadership, meaning, faith, and the pursuit of work that actually matters. With ...
96. What Are You Chasing?
We all chase something—grades, success, recognition, comfort, connection. Chasing can be good, but it can also lead us astray. In a world of likes, outrage, marketing hooks, and even AI pretending to be us, it’s easy to lose sight of what truly...
95. The Strategic Plan "Refresh"
Strategic plans used to be something boards revisited every three to five years. But today, the pace of change—and the unexpected shocks we’ve all lived through—are forcing boards to ask new questions: How do we stay involved over time? And how...
94. Lending Your Future Self a Hand
One of my most popular episodes was about building a personal knowledge management system. And here’s the surprising truth: the system itself matters less than the discipline of using it. Today, I’m sharing a simple life hack that’s saved me co...
93. Sell... sell... sell, baby... sell!
In my work with mission-driven organizations, I’ve seen how trust isn’t just a virtue—it’s a strategy. The way we initiate conversations says everything about our integrity, our intent, and our respect for others. Sales and development efforts ...
92. You have to have A system!
Forget the tools—do you have a system? In this episode, I explore why personal knowledge management isn’t about the latest app—it’s about discipline, consistency, and devotion. From steno pads to second brains, I discuss what separates...
91. Contemplating M&A: Pursuing the "cake and eat it too"!
Can you really have your cake and eat it too in nonprofit M&A? In this episode, we explore the mindset behind mergers, acquisitions, and strategic affiliations—not the math, but the meaning. When organizations face pressure to scal...
90. AI Makes It Easy. Or Does It?
In a world flooded with AI-generated content, standing out is harder than ever. In this episode, I explore what it really takes to rise above the noise—and why your unique voice matters more now than ever.Fountain pens. Film photography....
89. Running Through a Tunnel of Fire
What makes a team brave enough to face transformational change—together?In this episode, I explore the power of vision, trust, and storytelling in leading organizations through risk, resistance, and renewal.Listen in. The fire’s r...
88. Why Are Young People So Lazy?
“Why Are Young People So Lazy?” (Spoiler: they’re not.)A c-suite exec dropped that line—and it sparked a deeper dive into generational shifts, workplace loyalty, and what younger leaders really want.Listen in for a fresh take on w...
87. You've just been asked to become Interim CEO. Now what?
What does it really mean to step into the CEO role—especially as an interim? In this episode, I share lessons from my own experience leading organizations in transition, and offer practical advice for navigating the delicate balance between “ke...
86. Delayed Gratification
Organizations stuck in urgent crises often sacrifice long-term planning, focusing only on immediate fixes. This short-term mindset creates a cycle of unpreparedness that repeats itself. Building awareness of this pattern is the first step towar...
85. It Helps to Love What You Create
In this week’s episode, I dive deeper into a powerful lesson drawn from my journey as a photographer—why falling in love with what you create transforms not just your art, but your life and career. From average snapshots to meaningful images, I...