Leading Organizations That Matter

<p>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.<br /><br />Music by Kevin MacLeod at incompetech.com.<br /><br />Please feel free to listen and subscribe on one of these platforms...</p>

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 matters. Recently, a friend told me, ‘You seem to value authenticity.’ That simple observation made me pause and ask: What am I really chasing? In this episode, I explore how to reevaluate our pursuits, prioritize what matters, and choose authenticity ...

12-16
06:00

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 will we know when it’s time to shift? In this episode, I share three practical strategies that can give boards a clearer line of sight into progress, keep goals measurable, and build in a refresh point that ensures plans stay relevant. If you’re leadin...

12-09
05:11

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 countless times—because let’s face it, our future selves are often forgetful, distracted, and, well… a little doltish. The trick? Leave breadcrumbs. Clear instructions. Notes that anticipate what your future self will need, right when they’ll need it. Fro...

12-02
05:11

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 rooted in honesty build relationships that last. The rest? Just noise that is best ignored.

11-25
04:44

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 high performers from the forgetful, and why even seasoned executives need a system they trust.

11-18
05:44

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 scale without sacrificing identity, leaders are often sent on a quest for the impossible. Tune in as we unpack the cross currents, the trade-offs, and the conversations that matter most before the deal is even on the table.

11-11
04:39

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. Franklin Planners. Maybe the future isn’t faster. Maybe it’s more… rum raisinish.

11-04
06:09

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 real—but so is what’s on the other side.

10-28
04:41

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 what’s changing—and why it matters.

10-21
07:49

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 “keeping the seat warm” and truly leading. If you’ve ever been tapped to step up, this one’s for you.

10-14
05:25

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 toward breaking free and planning for a more sustainable future.

10-07
04:21

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 share how shifting focus from process to passion unlocks greater fulfillment and impact. Whether you’re navigating your career path or reflecting on what truly motivates you, this episode offers a fresh perspective on finding joy and purpose in the wor...

09-30
05:16

84. Planning versus Discovering

What do photography and career planning have in common? More than you’d think. In this episode, I share how years behind the lens—starting with a beat-up rangefinder—taught me the art of seeing, of waiting, and of wandering. Whether you're a sunrise-chasing planner or a thrill-seeking discoverer, this conversation explores how balancing preparation with openness can shape not just your images, but your life. Because sometimes, the best shot—and the best opportunity—is just around the bend.

09-23
05:41

83. Sometimes the Best Life Hacks are the Simplest

Accountability isn’t rocket science—it’s a notebook. In this episode, we skip the complexity and spotlight a painfully obvious yet wildly underused leadership tool: writing things down. From toxic cultures to missed follow-ups, we explore how a simple habit can transform organizational trust, clarity, and follow-through. No apps required. Just a pen, a plan, and a little discipline.

09-16
04:33

82. When Weakness Looks Like Power and Confidence Becomes Humility

What if the loudest leaders are the most insecure—and the quietest, the strongest? In this episode, we unpack a paradox at the heart of leadership: how humility, not bravado, shapes resilient cultures and lasting impact. From personal reflections to a poignant story of legacy and retirement, this is a candid exploration of what strength really looks like when the stakes are high. If you lead—or aspire to—you’ll want to hear this.

09-09
05:19

81. When Failure is the Norm

We all learned a lot about life, leadership, values, and priorities during the Covid pandemic. I recently was reminded of one while in the drive-through line at Starbucks.

09-02
04:31

80. Understanding the Diamond versus the Setting

Some mission driven organizations benefit from considering their purpose, their objective, their very reason for being as a diamond that is distinct from its setting. This week's quick episode is a thought experiment that several of my clients have found helpful. Perhaps you will as well.

08-26
03:45

78. Licking Our Wounds vs. Learning From Our Mistakes

Figuring out what went wrong and then learning from our mistakes is vital to an organization's long-term success and impact. Unfortunately, some organizations struggle to move past the woe-is-us wound licking phase. This is a topic of great interest to me personally and one I have studied and written about quite a bit. The key to progress here is for groups to lament... for a bit... and then to move forward into the learning mode. In this episode, I suggest a distinct and simple set of steps ...

08-12
06:42

77. The Search for Meaning at Work: Cutting Through the Mist

Finding meaning at work impacts organizational culture. Organizational culture impacts our ability to retain and hire the necessary talent for our mission driven organizations. Finding talent to fill our key positions is essential to the success of our "organizations that matter". In this week's episode, I discuss this phenomenon cut against the backdrop of the rapidly changing (i.e., for-profitization) of the hospice industry.

07-29
05:47

76. Jerry Seinfeld’s Surfing versus Yachting

I took a leap of faith, left behind the world I knew and tried to do something completely different. Yet somehow, in the process, I rebuilt everything I had just walked away from. For me, wisdom, insight, and inspiration came from the unlikeliest of sources: Jerry Seinfeld. Perhaps his own self reflection can help you too.

07-15
05:18

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