Many business leaders craft successful companies but only a few elevate that to the level of a masterpiece. What is it about some companies and leaders that allows them to achieve this status? How does the vision of ‘the good life’ differ across corporations, large and small?

Charles Spinosa is a management consultant and the author of several books. His latest book is called Leadership as Masterpiece Creation: What Business Leaders Can Learn from the Humanities about Moral Risk-Taking.

Greg and Charles discuss Charles’s vision of business leaders as artists and creators who shape organizations into masterpieces, rooted deeply in humanities and philosophy. The conversation covers various business leaders, including Jeff Bezos, and how their leadership styles create distinctive moral orders within their companies. Charles connects principles from Shakespeare, Nietzsche, and Machiavelli to modern business practices and explains how leaders can cultivate courage and virtue within their organizations. They also explore the differences between founders and inheritors of businesses, the role of leaders in shaping corporate culture, and the implications for leadership education.

*unSILOed Podcast is produced by University FM.*

Episode Quotes:

The three questions behind masterpiece leadership

18:05: My three questions are: What always goes wrong here? That tends to be an easy question for 80% of them to answer. What would you love to do instead? That is the hard question. That is the one you think is easy, but what would you love to do instead? That is hard because these men and women are geniuses at managing around what always goes wrong. They have been rewarded for managing around it, and they are good at it. And then, once we can get to “What would you love?”—what risks do you need to take to do what you would love? And that is where we begin to work out the kinds of risks, the hard risks they are going to take. Because when they make these changes, if they do not succeed, they are going to be seen as not just foolish, but actually evil. They have gone out and harmed people in careers and so forth. So we have to figure out those, and then we have to put them in a kind of strategic order. But that is, in short, my masterpiece-building strategy.

Leadership as a moral masterpiece

03:10: Masterpieces are not just attractive and compelling aesthetically. Masterpieces give us a distinct new way to live that we consider a good life. They are moral masterpieces, and they are morally distinctive.

Cultivating courage in organizations

42:34: It is not that hard to build a company that cultivates courage. When you realize that part of courage is realizing that you figure what you think is right, and then you compose a way for people to hear it.

Why leadership calls for admiration

22:15: I can admire Google, and I can admire Amazon. A lot of people cannot. I have had people walk out on me when I say that about Amazon. But choose another company—choose The Body Shop, choose Zuckerberg's company, Meta—quite different from Amazon. Again, if we can admire different companies, we do not have to embrace everything we admire, and that gives us a sense of different good lives that we can admire. And I want that to be the virtue that we develop, which is a step above tolerance. I mean, really, with tolerance, which is the modern virtue for dealing with difference, we tolerate things that are different that we cannot eliminate. They are too powerful. We do not consider them quite as good. We tolerate them, but it is never a happy tolerance.

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