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Description

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.Please feel free to listen and subscribe on one of these platforms...

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Check latest episodes from Leading Organizations That Matter podcast

114. They Wanted to Know About “the How”

2026/06/23

In this episode, I share a surprising moment after a guest lecture that made me rethink what people really want from leaders. The students didn’t care about my turnaround frameworks - they wanted to know how careers actually unfold: the choices, the pivots, the regrets, the risks. It pushed me to consider shifting the podcast slightly toward those deeper, practical questions about building a meaningful work life. I also talk about the future of the show... audio, video, or both... and invite your feedback as I chart the next chapter.

113. Does Faith Fit?

2026/06/16

In this episode, I wrestle with a question that’s become increasingly real for me: Does faith fit in our professional lives? For most of my career, I kept my faith and my work in separate rooms, door firmly shut. But lately, that door has been opening... through podcast guests, LinkedIn engagement, and the growing cultural hunger for something deeper and more enduring. I share what I’m noticing, why these conversations resonate, and I invite listeners to weigh in as I explore whether there’s more room for faith in the workplace than many of us may have once believed.

112. I’m Great at Multitasking - Yeah Right!

2026/06/09

In this episode of Leading Organizations That Matter, I dig into the myth of multitasking and how modern technology has rewired our brains. From the constant pull of screens to the illusion of productivity during Zoom meetings, I explore why we feel busier yet less present. I also highlight the growing cultural backlash... from vinyl records to dumb phones... and offer a simple, powerful practice to reclaim focus: batching. It’s a call to intentionality, mindfulness, and choosing presence over digital distraction.

111. The Importance of Disagreeing Well

2026/06/02

I’ve seen more harm come from avoiding conflict than from facing it. Leaders who fear tension often create cultures where silence becomes the norm... and that silence slowly corrodes trust, mission, and morale. In my book, Saving Organizations That Matter, I talk about why learning to disagree well is essential for any team that wants to grow. Disagreement, offered respectfully, is a gift. It sharpens thinking, strengthens relationships, and keeps the mission at the center. If you’re a leader who struggles with conflict - or you work in a culture that avoids it - I walk through a simple seven‑part framework that can help you rethink what disagreement is for.

110. The Power of the Preflight Checklist

2026/05/26

In this episode, I look at what leaders can learn from one of aviation’s simplest but most transformative tools: the pre‑flight checklist. After a fatal 1935 crash, Boeing realized that even expert pilots need more than confidence - they need a system. And leaders are no different. I break down how a checklist helps us reduce avoidable mistakes, anticipate turbulence, align our teams, and define success before we ever “take off.” And I share why consistent note‑taking and reflection are the foundation for building your own leadership checklists.

109. Here’s to the Pitchers

2026/05/19

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

2026/05/12

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 oddly indifferent, what’s at stake for human creativity, and why the “blank sheet of paper” still matters more than ever. Bottom line: If creativity becomes effortless… do we lose something essential about being human?

107. Why You Need to Write

2026/05/05

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 own unexpected path into journaling, I makes the case that putting pen to paper might be the most powerful tool you have for decision‑making, clarity, and growth. If you’ve been stuck, scattered, or second‑guessing yourself, this episode might just change how you think... by changing how you write.

106. Seeing the Forest AND the Trees

2026/04/28

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 instinctively focus on the smallest details. And more importantly, why the most effective leaders learn to do both. If you’ve ever wondered whether you’re seeing too wide… or too narrow… this conversation might just change the way you look at your organization.

105. Renee McInnes: Passion for the Mission

2026/04/21

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 the people who serve them. It’s an honest, energizing look at leadership in a time when health care needs it most. During this episode, I reference an earlier one on the topic of Medicare Advantage. Please see here for that episode.

104. Maureen Groden: When a Loved One Is Dying

2026/04/14

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 of life’s most tender passages. We talk about what to expect, how to stay present, and how small acts of love can become moments of profound meaning. If you’ve ever wondered how to show up when it matters most, this conversation is a gentle, grounding guide. To find out more about Maureen and her book, please click here.

103. I Wish That I Was More Data Driven

2026/04/07

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 dashboard of your organization. The other is about turning numbers into a story people will actually follow. If you’ve ever wondered why your metrics don’t move people - or why your decisions don’t land - this episode might change the way you lead.

102. Look at the Portfolio!

2026/03/31

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 selecting a coach or consultant.

101. Do We Have a Toxic Positivity Problem?

2026/03/24

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 and less authentic.

100. My War on Dis-Integration

2026/03/17

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 can quietly shape our lives and what it takes to move toward greater authenticity and integration. If you’ve ever felt like different parts of your life don’t quite connect, this episode offers a reflection on finding wholeness in the midst of modern leadership and modern living.

Podcast reviews

Read Leading Organizations That Matter podcast reviews

5 out of 5

8 reviews

★★★★★

Jman99bicknamw 2026/06/29

Gets you thinking

The content of this podcast is unlike many others. It offers information for you to absorb but is presented in a way that makes you think as well. Its...

★★★★★

BusinessQueen66 2024/03/12

Great content!

Definitely will be sharing this podcast with all coworkers, friends and family in business. Rey’s knowledge and experience really shines through in hi...

★★★★★

Rey rocks! 2024/03/12

Fantastic!

Rey brings a seasoned and well earned point of view to leadership and organizational development. He is a pleasure to work with IRL and a joy to liste...

★★★★★

MrsFiumes 2024/02/27

Sailing into the future with organizations that matter

I’m looking forward to this weekly podcast and Rey’s insightful and inspiring storytelling and recommendations for leading organizations that matter i...

★★★★★

Carolina_Pax 2024/02/24

Can’t wait to hear more!

I am immediately captivated by host's deep expertise and genuine passion for business. He clearly brings a wealth of knowledge, offering perspectives ...

★★★★★

lalalalalala guy 2024/02/23

Strong insights from a been-there, done-that thought leader

Concise, thought-provoking, and helpful. Adding to my list of commute podcasts

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