Boundaryless Conversations Podcast

• #130 - Thinking Beyond the Existing Theories: Evolution in Liminal Times with Dave Gray

  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 SuggestionsRemember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/gray-daveEpisode recorded on Nov 13, 25Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/Get in touch with Boundaryless:Twitter: https://twitter.com/boundaryless_Website: https://boundaryless.io/contactsLinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eoMusicMusic from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music

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• #129 - Why I Don’t Call it “Self-Management” Anymore - with Lisa Gill

  Lisa Gill - a coach, facilitator, and host of the acclaimed Leadermorphosis podcast - joins us to explore the evolving world of self-managing organisations.Drawing on over a decade of experience and examples from companies like Buurtzorg and her own work at TUFF Leadership, Lisa speaks about what makes radically decentralised organisations work: dynamic hierarchies, enabling structures, and accountability without coercion.Drawing on lessons from allied fields such as social justice and disability justice, she emphasises that accountability is a relational practice rather than a top-down mechanism, and that true accountability requires choice, trust, and transparent communication.This episode is packed with essential insights and practical nuggets that you can take back and reflect on, so don’t miss out.In this episode, Lisa takes us deep into the realities of implementing self-management and radically decentralised organisations in practice.Reflecting on the self-management movement's trajectory, she discusses the concept of the "green trap" - a common organisational sticking point - and uses it to emphasise why psychological comfort without sufficient accountability is unsustainable.She also covers several other core topics for the future of decentralised organisations - like the five organisational systems, the importance of inner shifts, what it means to create environments where people can sit in discomfort, learn, and grow without relying on coercion, and so much more.Key Highlights👉 Self-managing organisations thrive on dynamic hierarchies, enabling structures, and distributed decision-making rather than rigid top-down control.👉 Accountability works best as a relational practice grounded in choice, trust, and transparent communication, not coercion.👉 True accountability requires freedom: individuals must be able to say no for their yes to be meaningful and fully owned.👉 Balancing care and performance creates spaces for development where individuals and teams can grow sustainably.👉 Psychological safety paired with challenge fosters both learning and innovation, avoiding the traps of comfort or anxiety extremes.👉 Exposure to real consequences - like zero distance to customers - builds responsibility and encourages self-correcting behaviour.👉 Both market performance and human-centred care can coexist when organisations prioritise autonomy, clarity, and alignment on values.👉 Commitment-keeping and follow-through are foundational principles for self-managing, high-trust organisations.Topics /chapters(00:00) Why I Don’t Call it “Self-Management” Anymore - INTRO(01:22) Introducing Lisa Gill(03:19) Introducing Self-Management(11:41) Radically decentralised organisations and the future of Collaboration(19:03) Operationalizing Decentralization in Self-Managing organisations(24:56) Learnings on Self-Reflection from Allied Industries(30:10) What's the Future of Self-Management?(38:22) Enabling Ecosystemic Transformation(44:18) Breadcrumbs and SuggestionsRemember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/gill-lisaEpisode recorded on Oct 17, 25Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/Get in touch with Boundaryless:Twitter: https://twitter.com/boundaryless_Website: https://boundaryless.io/contactsLinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eoMusicMusic from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music

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• #128 - The Benefits of Programmable Organizations with Spencer Graham and Nicholas Naraghi (Hats Protocol)

  Spencer Graham and Nicholas Naraghi, co-founders of Hats Protocol, pioneering the design and experimentation of decentralised, programmable organisations, join us in this episode to explore how these new forms of collaboration can enable new ways to organise, govern, and create value collectively.They discuss the future of organisational design, including how AI agents can take on roles, how frameworks and reusable templates accelerate experimentation, and why adopting different role-based “Hats” can help individuals contribute meaningfully in new, decentralised ways.They also speak on how decentralisation can lower risk, increase system “hardness,” and improve predictability, while reflecting on what it means to distribute responsibility in a world where the boundaries of firms are increasingly fluid.Tune in to discover a more participatory way of organising that helps solve the principal-agent problem.Together, Spencer and Nicholas have been pioneering new ways of structuring DAOs and digital-native organisations, making roles programmable, modular, and resilient for several years now.In their work, they bring deep experience in building DAOs, governance frameworks, and infrastructure that allow organisations to operate with greater transparency, adaptability, and distributed decision-making.As we explore role-based structures to enable meaningful participation, we learn what it means to build adaptive systems capable of tackling complex challenges in a decentralised world.Key Highlights👉 Decentralised organisations reduce the cost of organising by embedding rules, roles, and incentives directly into software, minimising the need for traditional bureaucratic structures.👉 AI agents can take on organisational roles, augmenting human capabilities and enabling more modular, scalable coordination.👉 Lowering coordination costs increases the responsibility for individuals to participate meaningfully in organisational life.👉 Roles within organisations can be made programmable and modular, allowing for flexible experimentation and adaptation.👉 Reusable frameworks and templates accelerate organisational experimentation, letting groups test new coordination methods quickly.👉 Individuals may act like “micro-organisations” with AI agents representing them, but collaboration will always remain necessary for complex problem-solving.👉 Tokenisation and algorithmic governance allow individuals to earn ownership and rewards proportional to the value they create in an organisation.👉 Participating in decentralised organisations requires embracing uncertainty, both in outcomes and in coordination dynamics.Topics /chapters(00:00) The Benefits of Programmable Organizations(01:39) IntroducingSpencer Graham and Nicholas Naraghi (Hats Protocol)(03:35) From DAOs to Roles: The Birth of the HATS Protocol(10:11) The Principal-Agent Problem(15:00) Getting Buy-In on Protocols(22:03) Separating Tech from the Principal-Agent Problem(30:31) When Organizing Becomes Cheap: What New Organizations Will Emerge?(40:43) Uncertainty with Autonomy(46:05) Will “Organising” become a necessary skill?(49:05) Breadcrumbs and SuggestionsRemember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/protocol-HatsEpisode recorded on Oct 01, 2025Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/Get in touch with Boundaryless:Twitter: https://twitter.com/boundaryless_Website: https://boundaryless.io/contactsLinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eoMusicMusic from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music

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• #127 - Organising as World-Building: How AI & Platforms unlock Human Flourishing with Lee Bryant

  A thought leader and pioneer in platforms and ecosystems, partner at Speed Invest and an instructor at Reforge, Sameer Singh joins us on this episode to reintroduce the world of platforms, challenge the idea of AI as a platform shift, and talk about what makes products truly memorable in a market over-proliferated with choices. He helps us “Separate signals from the noise,” and shares his practical insights into what makes today’s startups investable: from founders with missionary zeal to data-informed decision-making, and so much more. For anyone curious about the intersection of AI-enabled consumer experiences and the evolving world of platforms, this episode is a must-listen.Sameer brings deep expertise in platforms with a sharp focus on scalable distribution models, retention, and core problem-solving. In this episode, he discusses his recent investments, framing generative AI as a powerful layer within the technology stack that can unlock new forms of multiplayer interactions and creative experiences.As always, he shares practical insights for entrepreneurs navigating the evolving landscape of marketplaces, social products, and what the future looks like for AI-enabled consumer experiences.Key Highlights👉 Organisations are evolving beyond rigid hierarchies as transaction costs fall and capabilities expand.👉 Building a resilient organisation requires focusing on platforms that enable value creation, not just managing people.👉 The “platform philosophy” allows organisations to extend beyond formal boundaries, inviting external talent and partners to participate.👉 World-building in organisational design creates a compelling culture and environment that attracts talent, fosters engagement, and drives innovation.👉 Automation, orchestration, and composability can empower employees to focus on high-value work rather than repetitive tasks.👉 Leaders need to act as architects of the workplace and navigators of uncertainty, rather than bureaucratic monitors.👉 Mapping organisational capabilities and continuously developing them is essential for strategic advantage, especially in knowledge-based and customer-facing work.👉 Agentic AI and other emerging technologies can become subsidised enablers, helping organisations build “machines that create machines.”👉 Employees can act as distributed designers: automating repetitive work and contributing to the evolution of the organisational platform.Topics /chapters(00:00) Organising as World-Building: How AI & Platforms unlock Human Flourishing - Intro(01:37) Introducing Lee Bryant(03:10) Thinking about Organisational Design from the edge(13:48) The Agent and Human Interaction(20:17) Composing Capabilities Across Boundaries(29:42) Balancing Humanity and Automation: Rethinking AI in organisations(36:04) Rethinking the idea of an organisation as transaction costs reduce(42:17) Building platforms that enable Value: Rethinking an organisation’s Core(51:24) Breadcrumbs and SuggestionsRemember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/bryant-leeEpisode recorded on Oct 2, 2025Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/Get in touch with Boundaryless:Twitter: https://twitter.com/boundaryless_Website: https://boundaryless.io/contactsLinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eoMusicMusic from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music

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• #126 - Network Effects, Generative AI, and Platform Shifts with Sameer Singh

  A thought leader and pioneer in platforms and ecosystems, partner at Speed Invest and an instructor at Reforge, Sameer Singh joins us on this episode to reintroduce the world of platforms, challenge the idea of AI as a platform shift, and talk about what makes products truly memorable in a market over-proliferated with choices.He helps us “Separate signals from the noise,” and shares his practical insights into what makes today’s startups investable: from founders with missionary zeal to data-informed decision-making, and so much more.For anyone curious about the intersection of AI-enabled consumer experiences and the evolving world of platforms, this episode is a must-listen.Sameer brings deep expertise in platforms with a sharp focus on scalable distribution models, retention, and core problem-solving.In this episode, he discusses his recent investments, framing generative AI as a powerful layer within the technology stack - that can unlock new forms of multiplayer interactions and creative experiences.As always, he shares practical insights for entrepreneurs navigating the evolving landscape of marketplaces, social products, and what the future looks like for AI-enabled consumer experiences.If you’re curious to learn how AI and platforms intersect to shape the next generation of consumer products, tune in.Key Highlights👉 True network effects are mathematically grounded and don’t change across technological eras.👉 Generative AI: is it a technology stack or a platform shift?👉 Single-user AI interactions do not inherently generate network effects. True network effects arise from unique, structured multiplayer interactions.👉 In consumer tech, founder background is less predictive of success; what matters more is the founder’s obsession with the problem and willingness to learn, and understand user behaviour.👉 For meaningful innovation, AI should enable new experiences or multiplayer interactions under the surface, rather than being exposed as a chat interface or standalone product. Direct, one-click AI interactions often reduce value and break potential network effects.👉 A true platform combines a usable product, developer tools, a way to match users with applications, and an economic incentive for developers.Topics /chapters(00:00) Network Effects, Generative AI, and Platform Shifts(01:22) Introducing Sameer Singh(03:07) Sameer’s Journey in Perspective(07:16) What is changing in consumer companies?(09:40) How do incumbent companies build for younger buyers?(11:04) AI and Platform Shifts(18:01) Building Solutions on GenerativeAI platforms(24:26) AEO and LLMs as a Distribution Channel(26:52) Does more content mean more action(29:41) Scepticism on AI Frenzy(37:59) Common threads among investable platform companies(44:09) Where does value lie in a Consumer Market(47:37) Breadcrumbs and SuggestionsRemember that you can always find transcripts and key highlights of the episode on our website: https://www.boundaryless.io/podcast/singh-sameerEpisode recorded on Sep 17, 2025Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/Get in touch with Boundaryless:Twitter: https://twitter.com/boundaryless_Website: https://boundaryless.io/contactsLinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eoMusicMusic from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music

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