Episode 48

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Published on:

28th Aug 2025

EP 48 - Leading Leaders Toward Masterpiece Creation: Translating Your Moral Vision into Business Reality Through Masterpiece Leadership

What if the critics and naysayers aren't a problem—but proof you're finally changing something that matters?

Charles Spinosa spent decades as both a Shakespeare professor and management consultant, giving him a unique lens on what separates true leadership from good management. His approach isn't about influence or operational excellence—it's about moral artistry. It’s about the courage to ask "what always goes wrong?" and then take the risks necessary to create something beautiful instead.

If you've ever felt like the person pointing out what's broken, if you have strong convictions about what's right even when it's unpopular, or if you're tired of managing around problems instead of solving them, this conversation will resonate deeply. Charles reveals why justice-sensitive and neurodivergent people often have a natural advantage in seeing what others miss—and how to turn that insight into transformational leadership. This episode will help you with leading leaders, and with seeing your own leadership development and career as a journey in masterpiece leadership.


Episode Highlights:

  • The two questions that define “masterpiece leadership:” What always goes wrong in your industry, and what would you love to do instead?
  • How to distinguish between dissenters (who sharpen your vision) and betrayers (who undermine it).
  • Why naysayers are often a sign that you’re taking the right kinds of risks.
  • The neurodivergent advantage: spotting injustices and anomalies others overlook.
  • Practical strategies for pushing through despair when moral risks don’t pay off right away.
  • Justice sensitivity as a leadership strength—and how it positions you to create businesses worth falling in love with.

Key Concepts Explored:

  • Passion as a defining force that fuels resilience and long-term transformation
  • The Two-Question Framework that separates masterpiece creators from managers
  • Moral risk-taking: why changing norms will always feel “wrong” at first
  • Betrayers vs. dissenters—and why dissent is essential for progress
  • Truth-seeking platforms that go beyond psychological safety to real intellectual conflict
  • Post-truth business culture and the limits of data without human truth
  • Justice sensitivity as a leadership advantage for transformational change
  • The neurodivergent edge in spotting anomalies and injustices others miss
  • Moral artistry: making solutions not just right, but beautiful
  • Fighting through despair and returning to core beliefs during setbacks
  • Awe and wonder as signals you’re on the right path
  • A systemic change strategy for moving from easy wins to bold transformations

Common Questions Answered:

  • How can you take moral risks without putting your career in jeopardy?
  • What separates managers from masterpiece creators?
  • How should leaders handle team resistance to moral change?

Notable Quotes:

"What do people say leadership is these days? They say leadership is influence. I'm saying no. Leadership is taking moral risks to establish morally distinctive masterpieces. So I'm overturning a lot of norms. Of course there are gonna people who hate that." – Charles Spinosa [00:34:19]

"So if I'm not hearing from naysayers, I might not be taking as much risk as I think I am, or as much risk as I could in pursuing a defining passion. That hearing from critics and naysayers says you're doing something different enough for people to have naysaying to do about it." – Sara Lobkovich [00:33:18]

"Always be sensitive to what's going wrong in your organization. And don't forget to ask what you would love instead. And try to make the solutions you offer beautiful." – Charles Spinosa [00:32:57]

"So if you're a leader, you are trying to make a moral vision come true. You want to make it profitable. You wanted people to see that what you see is the right way to do business in your industry, in your organization. And those hits are hits to your heart. They're not just hits to the bottom line. And you take three hits to the heart — bam, bam, bam — in a row. My experience is that's very hard." – Charles Spinosa [00:09:56]

"The thing to do is to ask yourself, What do I believe to be true? What do I believe to be true about my customers? Most importantly, what do I believe to be true about my employees? What do I believe to be true about me?" – Charles Spinosa [00:10:22]

"Hearing from critics and naysayers says you're doing something different enough for people to have naysaying to do about it." – Sara Lobkovich [00:33:40]

Chapters:

[00:00:00] Introduction to Masterpiece Leadership and Moral Vision

[00:02:00] Defining Leading Leaders

[00:03:00] The Masterpiece Creation Framework: What Always Goes Wrong?

[00:04:00] Moral Risk-Taking: Building Systematic Change

[00:05:00] The Importance of Leading Leaders in Organizations

[00:07:00] Anita Roddick and The Body Shop: When Events Force Bigger Risks

[00:09:00] Fighting Through Despair: When Moral Visions Take Hits

[00:10:00] Masterpiece Leadership Principles for Moral Risk-Taking

[00:14:00] Real-World Examples of Masterpiece Leadership

[00:16:00] The Problem with Post-Truth Business Culture

[00:17:00] Betrayers vs. Dissenters: Building Truth-Seeking Teams

[00:19:00] Strategies for Leading Leaders Effectively

[00:21:00] Justice Sensitivity as Leadership Strength

[00:23:00] Overcoming Challenges in Masterpiece Leadership

[00:25:00] Defining Passion and the Power of Awe and Wonder

[00:26:00] The Story That Made You: Finding Your Core Virtue

[00:28:00] Building a Culture of Masterpiece Leadership

[00:29:00] The Neurodivergent Advantage: Seeing Anomalies Others Miss

[00:30:00] Charles's Personal Story: From Dyslexia to Philosophy Professor

[00:32:00] Avoiding Neurodivergent Snobbery While Leveraging Differences

[00:33:00] Next Steps for Aspiring Leading Leaders in Business Reality

[00:34:00] Why Critics Mean You're Changing Something Important

[00:35:00] Closing Thoughts on Masterpiece Leadership and Leading Leaders

Guest Information:

  • Charles Spinosa is a management consultant with 28 years of experience working with Fortune 100 companies and startups across North America, Europe, and Latin America. He brings a unique philosophical perspective to business leadership, having started his career as a Shakespeare professor at UC Berkeley studying "defining passions" in literature before transitioning into consulting work focused on leadership development, culture change, and innovation.
  • Charles is the author of "Leadership as Masterpiece Creation: What Business Leaders Can Learn from the Humanities about Moral Risk-Taking," which challenges conventional wisdom about influence-based leadership. As someone who is neurodivergent and dyslexic, he advocates for leaders who see anomalies and injustices that others miss, helping them transform moral vision into business reality through systematic risk-taking and what he calls "moral artistry."
  • His work centers on helping leaders move beyond managing around problems to creating something genuinely beautiful and transformative, even when facing resistance from teams, boards, and entire industries.

Connect with Zeph:

  • LinkedIn: Charles Spinosa
  • Book: "Leadership as Masterpiece Creation: What Business Leaders Can Learn from the Humanities about Moral Risk-Taking" available wherever books are sold

Sara’s Links and Resources:

Upcoming Events:

  • Catch Sara at the World OKR Summit! She’ll be speaking this October 30–31: okrsummit.org

Find full show notes and the episode transcript via https://findrc.co/thinkydoers.

Mentioned in this episode:

Don't forget your free No-BS OKRs Workbook

Before I let you go, I just wanna remind you, you can pick up your copy of "You Are a Strategist: Use No-BS OKRs to Get Big Things Done" at https://youareastrategist.com, and you'll get that free PDF of the "No-BS OKRs Workbook" when you purchase direct. Don't wanna DIY it? Book a VIP executive strategy day with me. They can be used one-on-one. It can be used to facilitate an in-person or remote event with your org. It can also be used for a keynote that inspires actual results for your upcoming event. Visit https://findrc.co/vipday for all the details. And from there you can book a free executive strategy intake call, or request a no meeting virtual consult. A VIP executive strategy day helps you unlock clarity, align quickly, and drive results in just one powerful day.

Don't forget: Get your free No-BS OKRs Workbook or schedule a VIP Strategy Day!

Before I let you go, I just wanna remind you, you can pick up your copy of "You Are a Strategist: Use No-BS OKRs to Get Big Things Done" at https://youareastrategist.com, and you'll get that free PDF of the "No-BS OKRs Workbook" when you purchase direct. Don't wanna DIY it? Book a VIP executive strategy day with me. They can be used one-on-one. It can be used to facilitate an in-person or remote event with your org. It can also be used for a keynote that inspires actual results for your upcoming event. Visit https://findrc.co/vipday for all the details. And from there you can book a free executive strategy intake call, or request a no meeting virtual consult. A VIP executive strategy day helps you unlock clarity, align quickly, and drive results in just one powerful day.

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Thinkydoers®
Leadership and career when you're at odds with mainstream business culture
Thinkydoers®, hosted by Strategy Rebel and OKR Coach Sara Lobkovich, is a community for unconventional leaders, status-quo challengers, and workplace “square pegs.” Thinkydoers are individuals who navigate the journey from insight to idea, through the messy middle, seeking courage and confidence to bring their visions to life.

Thinkydoers are a diverse group. We're disproportionately (but not exclusively) introverted and/or neurodivergent, and regardless of personality or cognitive wiring, Thinkydoers are strategic thinkers often underserved and misunderstood in traditional business cultures. Whether you’re a leader, an aspiring leader, or a behind-the-scenes “clutch player,” Thinkydoers aims to help you find more satisfaction, less frustration, and greater flow in your work.

Learn to unlock your inner strategist with No-BS OKRs. Then, explore topics way beyond goal-setting, including strategy, behavior change, cognitive health, and motivation. Our guest episodes feature a wide range of perspectives to support you in building the work/life you want most.

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Sara Lobkovich