Red Sail Advisors LLC

Consulting to Mission Driven Organizations

95. The Strategic Plan “Refresh”

This week’s episode – click here. 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?…

94. Lending Your Future Self a Hand

This week’s episode – click here. 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…

93. Sell… sell… sell, baby… sell!

Here’s this week’s episode – click here. 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…

92. You have to have A system!

This week’s episode – click here. 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…

91. Contemplating M&A: Pursuing the “cake and eat it too”!

Here’s this week’s episode. 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…

90. AI Makes It Easy. Or Does It?

Today’s episode: click here. 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…

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.

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.

87. You’ve just been asked to become Interim CEO. Now what?

What does it really mean to step into the CEO (or any other key leadership position for that matter) 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…

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.

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.…

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…

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…

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…

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. 

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.

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 number of conversations with individuals who can relate. I sometimes then…

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…

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…

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…

75. Susan Keane Baker: Best Intentions and the Patient Experience

“You’re never sorry you were kind…” 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 elevating the patient experience. Thank you to Susan for…

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 discuss the implications of high change readiness and the actions you can take if you encounter low…

70. Are You Unbalanced or Disintegrated?

This week, I discuss the connection and differences between having a sense of balance versus integration in your life. And no plates were harmed in the production of this episode.

69. Toward Hope and Healing: The Ignatian Spirituality Project

I’m pleased to interview three guests today from The Ignatian Spirituality Project, an organization that surely “matters”. It’s a conversation about hope and healing… and second chances and redemption. I hope you’ll find this to be inspiring. For more information, see here.

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