Playful Thinking Under Pressure

Playful thinking under pressure, with cas holman and michelle lee on ideo's creative confidence podcast

“I received a call from someone saying, ‘You don’t know me, we’ve never met, I’m a big fan of your work — and I just wanted you to know you’re being knocked off in China,’” Cas Holman recalls of a pivotal moment in her career as a play and toy designer.

What followed wasn’t a legal battle. It was a reframing guided by the playful mindset she brings to her work. And it led to a surprising outcome.

In this Asked & Answered edition of the Creative Confidence Podcast, host Mina Seetharaman is joined by Cas Holman, creator of Rigamajig and author of Playful, and Michelle Lee, IDEO Partner and Executive Co-Managing Director, to explore what a playful mindset looks like in practice in real work settings.

Together, they respond to listener questions about competition, psychological safety, cross-organizational collaboration, and how leaders can bring curiosity into environments that don’t always reward it. Below are summaries of their answers. Listen to the podcast episode for the full conversation.

Listen to the first part of our conversation with Cas and Michelle for insight on how to rethink play as a leadership skill.

Listen on Apple, Spotify, YouTube or wherever you get your podcasts.


Article Summary

How can a playful mindset guide tough business decisions?

How can leaders collaborate across organizations without losing their competitive edge?

How do you create psychological safety when time is limited?

What are simple ways to invite play into meetings?

Is play different from brainstorming?

Can play exist in high-stakes domains like policy or healthcare?

 

How can a playful mindset guide tough business decisions?

Cas: When she learned her toy invention Rigamajig was being copied in China, her first move wasn’t legal action. She reframed the situation using a name-by-function approach. Instead of asking, “How do I stop this?” she asked, “What are we actually after here?”

If the goal was spreading playful learning—not just protecting IP—then litigation might not serve the deeper purpose. That shift opened up new options aligned with her values.

Insight: Under pressure, a playful mindset helps leaders respond in alignment with their values instead of out of reflex or fear.

How can leaders collaborate across organizations without losing their competitive edge?

Michelle: Parallel play can be a useful model for business collaboration. At the Consumer Electronic Show (CES) event, I found inspiration in organizations sharing their new explorations in proximity without necessarily collaborating. The openness didn’t eliminate competition. It expanded the collective field of possibility.

As a member of the Aspen First Movers Fellowship, a program for social entrepreneurs, I experience something similar. I can be vulnerable about what I’m struggling with when I know the other members are working through similar challenges. 

Insight: Collaboration doesn’t require revealing your strategy. Share questions and experiments, not trade secrets. Shift from fear-driven secrecy to possibility-driven openness.

How do you create psychological safety when time is limited?

Cas: Start with something deceptively simple: ask participants to recall a short memory of play from childhood. There’s no elaborate setup and no pressure to be vulnerable in the present moment. Sharing a memory can feel safer than sharing an opinion. It reconnects people to curiosity without asking them to perform.

Michelle: Safety is often designed physically before it’s built emotionally. Smaller tables instead of large rooms. Pair work before full-group sharing. Gradually expanding social exposure instead of asking people to speak up immediately. Thoughtful room layout and sequencing matter.

Insight: You don’t need a grand gesture to create safety. Right-size the invitation to the time, space, and structure available to you.

What are simple ways to invite play into meetings?

Michelle: Try this exercise: ask a group to pair up and pass an object back and forth. Then repeat, but without using their hands. The constraint makes it awkward, harder—and more fun. The added challenge creates satisfaction. People feel the difference immediately. Movement, challenge, and shared laughter shift the energy of the room in ways that words alone cannot.

Insight: Experience changes behavior faster than explanation.

Is play different from brainstorming?

Cas: Playful thinking follows some of the same rules as brainstorming or improv: embrace possibility, suspend judgment, allow for wrong answers. 

Michelle: Brainstorming can be playful, but not all brainstorms are play. When stress, performance pressure, or subtle judgment enter the room, play disappears. The format might look creative, but the mindset isn’t.

Create a playful tone in brainstorms using IDEO techniques like “Etch-A-Sketch for the Brain” and mash-up brainstorms that pair dreaded tasks with loved activities. 

Insight: The format doesn’t guarantee the energy.

Can play exist in high-stakes domains like policy or healthcare?

Michelle: High-stakes environments are not incompatible with play. Many constraints are assumed rather than real. Simply reframing an initiative as an experiment can create permission to test small changes.

In one IDEO project focused on nurse shift changes, the team encountered resistance to altering an entrenched process. By questioning an accepted rule and running structured experiments, they uncovered unexpected benefits for patients and staff alike. Play showed up as myth-busting and disciplined testing—not games.

Cas: In high-risk environments, leaders must actively model vulnerability. Go first. Offer the weird idea. Intentionally lower the bar. Even naming the moment—“I’m playing here”—can create permission for others to explore.

If leaders feel they must offer the smartest idea first, they shut down the room before it even begins.

Insight: In high-stakes environments, leaders must actively rebalance power dynamics to unlock creative thinking.

 

Keep Exploring Playful Thinking

Read Cas Holman’s book 

Playful: How Play Shifts Our Thinking, Inspires Connection, and Sparks Creativity  

Learn with Michelle Lee at IDEO U

Creative Thinking for Complex Problem Solving — Tap into the power of imagination to tackle complex problems. 

Related Blog Posts

How a Playful Mindset Leads to Better Work

The Power of Play: How to Solve Problems Like a Toy Designer

Play at Work: 7 Ways to Shift Your Mindset and Unlock Innovation

Listen to more podcast episodes

Subscribe to the Creative Confidence Podcast to hear conversations with today’s most thoughtful creative leaders and explore past episodes at ideou.com/podcast

 

About the Speakers

Cas Holman

Founder of Rigamajig and Author of Playful

LinkedIn

Cas Holman is the founder and chief designer of the toy company Heroes Will Rise and a former professor of Industrial Design at RISD. Cas travels the globe speaking about playful learning, the design process, and the value of play in all aspects of life. She has shared her perspective in workshops and seminars with teams at Google, Nike, LEGO Foundation, Disney Imagineering, and art museums around the world. Some of her designs include toys like Rigamajig and Geemo, as well as play experiences at the High Line and the Liberty Science Center. Cas is author of Playful: How Play Shifts Our Thinking, Inspires Connection, and Sparks Creativity (October 2025, Avery, an imprint of Penguin Random House) with science writer Lydia Denworth about the importance of free play for adults. Cas lives in Brooklyn and designs from her studio in the Catskills, New York. 


Michelle Lee

Partner and Executive Co-Managing Director, IDEO 

LinkedIn

Michelle Lee is an IDEO Partner and Executive Co-Managing Director, where she helps lead IDEO’s San Francisco studio and the IDEO Play Lab. With a background spanning toy design, user research, product management, and design leadership, Michelle brings a deep understanding of how playful thinking can unlock creativity in complex, real-world contexts. At IDEO, Michelle works with organizations across industries—including education, healthcare, and consumer products—to apply play as both a mindset and a method for tackling ambiguity, engaging teams, and driving meaningful change. Michelle regularly speaks and writes about her passion for play, including presentations at SXSW, The Delight Conference, The Culture Summit, Circularity 23, and educational institutions and organizations around the world, inviting audiences to reimagine the power of play in shaping meaningful futures.


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