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.
Please feel free to listen and subscribe on one of these platforms...
Episodes
97 episodes
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...
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Season 2
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Episode 96
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6:00
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...
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Season 2
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Episode 95
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5:11
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 co...
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Season 2
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Episode 94
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5:11
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 ...
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Season 2
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Episode 93
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4:44
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...
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Season 2
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Episode 92
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5:44
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 scal...
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Season 2
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Episode 91
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4:39
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....
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Season 2
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Episode 90
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6:09
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 r...
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Season 2
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Episode 89
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4:41
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 w...
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Season 2
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Episode 88
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7:49
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 “ke...
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Season 2
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Episode 87
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5:25
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 towar...
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Season 2
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Episode 86
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4:21
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...
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Season 2
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Episode 85
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5:16
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 su...
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Season 2
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Episode 84
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5:41
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 expl...
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Season 2
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Episode 83
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4:33
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 ...
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Season 2
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Episode 82
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5:19
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.
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Season 2
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Episode 81
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4:31
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 ...
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Season 2
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Episode 80
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3:45
79. How to Quit a Toxic Company
"Should I Stay or Should I Go?"... sang The Clash all the way back in 1982. Let's say you have been debating this same question at your job... and ultimately conclude: I'm so done here.As an executive coach, I have been in a num...
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9:23
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 int...
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Season 2
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Episode 78
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6:42
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 t...
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Season 2
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Episode 77
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5:47
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 unlikelie...
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Season 2
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Episode 76
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5:18
75. Susan Keane Baker: Best Intentions and the Patient Experience
This week, I discuss the impact of busyness on the business of health care with author and expert, Susan Keane Baker. We review issues related to kindness, accountability, presence, leadership, and the state of the industry when it comes to ele...
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Season 2
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Episode 75
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39:11
74. There's Change and Then There's Change Readiness
You need to determine whether change is necessary and then, if so, how best to accomplish that change. This week, I offer another important question that must be considered: is the organization ready for that change? I then disc...
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Season 2
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Episode 74
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6:46