610: Cas Holman on Play, Creativity, and the Future of Work
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Release Date: 12/15/2025
617: Inc 5000 fastest growing company on Psychology behind leadership influence and human behavior (with MichaelAaron Flicker)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Michael explains that people often struggle because “adding and adding must be more effective,” yet humans are “more confident when just one advantage is presented.” He shares that Five Guys succeeded because they “only do burgers and fries” and that “if you say you are best at one thing most of all, they’re more likely to believe that.” He emphasizes that “buyers…have a top force-ranked prioritization of the most important thing,” and focusing on the thing you are “best in the world at” is “more believable and more memorable.” On pricing, he notes that...
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616: NYU Stern’s Prof on How AI Is Rewriting the Future of Work (with Ben Zweig)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
When most executives discuss AI, they focus on automation. Dr. Ben Zweig, NYU Stern professor and CEO of Revelio Labs, explains why the real disruption isn’t machines replacing people, it’s our failure to rethink how work is structured. “Labor markets are not as sophisticated as capital markets,” Ben explains. “We allocate capital efficiently, but not labor. That’s a huge weakness in how our economy operates.” In this conversation, we explore: Why every company must learn job architecture, seeing jobs not as titles, but as bundles of tasks that must constantly evolve. The...
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615: $12B Investment Firm CEO on Saving the American Dream (with Mark Matson)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this conversation, Mark explains that “we often build our lives on things we are certain about that simply are not true.” He describes how “we don’t actually see the world… we see screens of how we think the world is.” He explains that these screens create “a double paradox” shaping what we think is safe, what we think is risky, and how we choose to act. Mark describes the difference between someone who sees a large employer as stability versus an entrepreneur who sees it as danger, saying “which screen is right? Well, it depends on which screen is going to give you more...
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614: Why Executive Leaders Feel Lonely
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Adam McGraw is a Fortune 100 VP turned entrepreneur and co-founder of a leadership community. “We try and really curate it for folks that are in the VP and above through CEOs as well, founders, etc., so that they have this kind of safe white space atmosphere to really consistently plug in and build community.” “Not just transact network-wise in things that are typically narrow and niche… we really love the idea of a melting pot for leaders.” “This is kind of the new normal: constant change, constant uncertainty, constant transition.” “Being in crew keeps me grounded and...
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613: Microsoft CTO on AI, Human Agency and the Future of Work
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Technology is reshaping the world at a pace few people, inside or outside the industry, expected. But every so often, you meet someone who has not only witnessed the major waves of technological change, but helped build them. In this conversation, Marcus Fontoura, Technical Fellow and Corporate Vice President at Microsoft, CTO for Azure Core, walks us through the story of AI, what leaders are getting wrong, and how to develop the one thing that will matter more than any model or algorithm: human agency. Marcus has lived through every major inflection point: early search, the rise of cloud...
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612: How to Have More Hope with Dr. Julia Garcia
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this episode, Dr. Julia Garcia explains why hope is a habit and why it is critical for us to remove what blocks hope. She describes what happens inside teams when leaders lose hope, including “the culture that creates, the burnout that leads to, the discouragement and defeat.” Julia shows how unprocessed emotions drain leaders even when they appear high-functioning. “If we emotionally feel disconnected, we’re going to start looking elsewhere or we’re going to end up in a place of hopelessness where maybe we completely shut down in our career and now we’re just a robot.” One of...
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611: Former U.S. Intelligence Officer on AI, Leadership, and Thinking Like a Spy (with Anthony Vinci)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this conversation, Anthony Vinci explains that “AI is going to be able to do more and more of what people do.” He describes a future where “AI is going to get better and better at doing what people do,” and highlights that leaders must understand “how do you figure out what AI is good at and then implement it to do that” and “how do you manage your workforce so that they are able to partner with that AI.” He warns that leaders often “overestimate what AI can do and underestimate it at the same time,” and stresses the importance of “getting that balance right.” As he...
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610: Cas Holman on Play, Creativity, and the Future of Work
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
When was the last time you played, really played? For Cas Holman, founder and chief designer of Heroes Will Rise and star of Netflix’s Abstract: The Art of Design, play isn’t childish. It’s the foundation of human creativity, resilience, and connection. She worked with LEGO, Disney Imagineering, and the LEGO Foundation and on a mission to help adults rediscover what children know instinctively: that play is how we learn, adapt, and feel alive. “Play isn’t what happens after work,” Cas explains. “It’s how we manage uncertainty. It’s how we cope, experiment, and find our way...
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609: UCLA Professor and MD on How Gravity Shapes Your Health and Mind
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Dr. Brennan Spiegel, Director of Health Services Research at Cedars-Sinai and Professor of Medicine and Public Health at UCLA, author of the book Pull, explains why illness is often a failure to manage gravity. He describes how our relationship with gravity defines strength, balance, digestion, mental stability, and emotional health. Take the Gravotype Quiz at to identify how your body manages gravity. Key Insights and Action Steps — Dr. Brennan Spiegel “Every single cell of your body evolved from this force of gravity. Physics came first, and biology came second.” Illness arises...
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608: Harvard Professor and former CEO of Medtronic, Bill George, on How Leaders Should Manage Challenging Times
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Bill George, former CEO of Medtronic and Harvard Business School Executive Fellow, explains how leaders can stay grounded, principled, and effective in chaotic times. “It’s a world of chaos and it requires a very different kind of leader than in more stable times.” The skills that once mattered (process control, long-term plans) are now secondary to courage, self-awareness, and moral clarity. George says most executives still lead comfortably “inside the walls” but fear the external world (media, public scrutiny, and rapid change). “Today, if you’re a leader, you are a public...
info_outlineWhen was the last time you played, really played?
For Cas Holman, founder and chief designer of Heroes Will Rise and star of Netflix’s Abstract: The Art of Design, play isn’t childish. It’s the foundation of human creativity, resilience, and connection. She worked with LEGO, Disney Imagineering, and the LEGO Foundation and on a mission to help adults rediscover what children know instinctively: that play is how we learn, adapt, and feel alive.
“Play isn’t what happens after work,” Cas explains. “It’s how we manage uncertainty. It’s how we cope, experiment, and find our way through the unknown.”
In this conversation, Cas reframes play not as a distraction from productivity but as the engine of it.
She explains why play is essential for innovation, executive presence, and emotional agility, and how suppressing it has drained creativity from our professional lives.
“Playful thinking lets us reframe success,” she says. “It makes us flexible enough to keep moving when things don’t go according to plan.”
We discuss:
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Why free play (activities that are intrinsically motivated, freely chosen, and personally directed) is the most powerful form of creative renewal.
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How reframing success turns frustration into discovery:
“You came to play basketball, the ball’s flat, the court’s full, so what? Invent a new game.” -
Why curiosity and uncertainty are not threats to be managed, but conditions for growth.
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How “breaking” systems or routines can reveal how they actually work.
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And how adults can learn to release judgment, the internal critic that says “I should know the answer” instead of “let’s find out.”
Cas’s insights are strikingly relevant to the age of AI. As technology automates more of what we do, she reminds us that what matters most is how we create, not how efficiently we delegate creation.
“We’re outsourcing the wrong things,” she says. “Creativity wasn’t the problem that needed fixing. It’s what makes us feel alive.”
Get Cas' book, Playful, here: https://shorturl.at/jxR4O
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