No handoff: embedding experiments into business

Dave Gray, acclaimed author and designer, joins us in this episode to explore how organisations can navigate profound technological and societal shifts by thinking outside their traditional theories.
With his decades of helping organisations rethink their value architectures, and his work on liminal thinking and visual frameworks, he reflects on how AI, and other fast-moving cultural changes are reshaping the very assumptions businesses operate on.
We also discuss why the biggest opportunities emerge outside a company’s existing theory, how architectural innovation differs from component optimisation, and why loosening organisational structures can create more space for play, experimentation, and discovery.
Tune in as we learn to embrace ambiguity, enable play, and help design companies that evolve with the liminal times we’re all living through.

Throughout his career, Dave has been a leading voice in helping organisations make sense of complexity. He has co-authored Gamestorming, a foundational playbook for collaborative problem-solving, and written several other seminal books that pioneered reframing organisations as adaptive, networked systems and embracing change.
In this episode, he shares his experiences from his newer ventures like the “School of the Possible”, and “Visual Frameworks”, helping us reframe our mental models and being able to “see differently,”.

Key Highlights
👉 Organisations struggle to see signals outside their existing theory, categories and mental models: ones that make them efficient but also make them blind during liminal times.
👉 Customers are constantly evolving - which means they often see shifts in value long before organisations do. Paying attention to customers is one of the most reliable ways to notice what’s changing outside your existing theory.
👉 Innovation requires the ability to visualise and hold ambiguity - letting go of familiarity to notice what doesn’t fit the current map.
👉 Architectural innovation means breaking the system into pieces and reassembling it from first principles - not just optimising components.
👉 Failure is essential - most experiments will fail, but a few (like AWS for Amazon) can redefine the complete business.
👉 Paying attention to anomalies and accidents can unlock entirely new markets.
👉 You can’t think your way into a new worldview, but you act your way into one through play, prototyping, and exploration.
👉 Looseness, redundancy, and play at the edges enable organisations to notice weak signals and adapt faster than tightly optimised systems.

Topics /chapters
(00:00) Thinking Beyond the Existing Theories: Evolution in Liminal Times
(01:30) Introducing Dave Gray
(03:57) At the Inflection Point: AI, Media, and the End of Business as Usual
(21:04) Building Constraints in Innovation
(24:38) The Outside-In Perspective for Organisation Building
(31:21) Building businesses with new theories of value
(42:48) What’s the future of customer co-creation?
(48:18) Breadcrumbs and Suggestions

Remember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/gray-dave

Episode recorded on Nov 13, 25

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Music

Music from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music