EPISODE OVERVIEW What if the biggest obstacle to creating change in your organisation isn't a lack of resources, effort, or intention — but the questions you're asking? That's the central challenge Hildy Gottlieb has spent 30 years answering, and it cuts right to the heart of what purpose-driven leadership actually requires. Hildy Gottlieb is a futurist, social scientist, and the developer of Catalytic Thinking — a question-based framework for systems change published in the Stanford Social Innovation Review and used by nonprofit leaders, social entrepreneurs, and purpose-driven businesses around the world. Over three decades working with community organisations, Hildy and her partner Dimitri Petropolis made a confronting discovery: the tools most organisations rely on to pursue change — strategic planning, resource development, board governance — were never designed to create the world we want. They were designed to maintain the world we have. In this conversation, Hildy unpacks the deceptively simple maths behind why most change efforts stall, walks us through the seven questions of Catalytic Thinking, and makes a compelling case for why the most important thing a purpose-driven leader can do right now — in business, nonprofit, or social enterprise — is dream bigger, not smaller. Listeners can expect actionable ideas for leaders in nonprofit, social enterprise and business who want to move from reactive fixes to ambitious, inclusive change — starting with one simple shift: change the questions, change the world. WHO THIS EPISODE IS FOR This episode is for you if you're a CEO, nonprofit leader, social entrepreneur, sustainability or ESG leader, or anyone responsible for organisational strategy and culture who: Wants to move beyond incremental, reactive change toward genuine systems change Is grappling with how to embed purpose more deeply into how your organisation plans and operates Leads teams and wants to unlock more creativity, inclusion, and collective ownership Is navigating a difficult external environment and looking for a framework that builds resilience and hope alongside action Is curious about what inclusive leadership and stakeholder-centred strategy actually looks like in practice ABOUT HILDY GOTTLIEB Hildy Gottlieb is the co-founder of Creating the Future and the developer of Catalytic Thinking — a framework for social change rooted in neuroscience, mathematics, and economics. Her work has been published in the Stanford Social Innovation Review, and her SSIR article on Movements vs. Organizations was selected to open their ebook Essentials of Social Innovation: Transforming Leadership — and directly inspired the design of the Community Centric Fundraising movement. Hildy is a TEDx speaker and the author of multiple books used as texts in undergraduate and graduate programs around the world. With her partner Dimitri Petropolis, she co-founded the world's first Diaper Bank, sparking a movement across North America and earning a Points of Light Citation from President Bill Clinton. She helped develop the Masters degree program in Community Leadership at Duquesne University (pron. Dew-cáyne), where she and Dimitri taught as professors, and has lectured at institutions including UC Berkeley and the University of Waikato in New Zealand. Her forthcoming book, How to Create the Future, distils 30 years of research and demonstration projects on what actually creates lasting change. WHAT WE COVER IN THIS EPISODE Why love isn't just welcome in business — it's essential to good decision-making, and why its absence leads to what Hildy calls 'really dumb decisions' How Hildy and Dimitri moved from commercial real estate to founding a social change movement — and what values drove that journey The five-year wake-up call: why doing nonprofit strategic planning 'the right way' produced good reputations but no community change The maths that changes everything: why less bad does not equal good, and what the number line from minus one to plus one reveals about how organisations set their ambitions Why most organisations are aiming at zero — and how Catalytic Thinking reorients purpose-driven leaders toward the positive future they actually want to create The seven questions of Catalytic Thinking, grouped into Radical Inclusion, Radical Possibility, and Radical Strength Why the first question — who will be affected, and what will it take to include them — changes everything downstream in organisational planning Radical Inclusion vs. target marketing: why centering your community (not your organisation) produces fundamentally different strategy Why strategic planning inherited from the military and church charity was never designed to create systems change — and what to use instead The Amy's Organic Foods story: what a small startup learned about collaboration by calling one of the world's largest frozen food companies Why money is not a resource — and the concept of Collective Enoughness that transforms how organisations think about what they already have The AIDS coalition story: how asking 'what does good look like for the whole community?' led to orange T-shirts and a breakthrough in HIV prevention among seniors How purpose-driven leaders can hold onto hope and long-term vision while navigating a world that feels like it's moving backwards Why simultaneously resisting what's wrong and creating what's possible is the only path out of playing defence forever KEY INSIGHTS Less bad is not the same as good — and the maths proves it Hildy uses a simple number line — minus one to plus one, with zero in the middle — to expose a structural flaw in how most organisations pursue change. When success is defined as eliminating a problem, we're aiming at zero: a world without poverty, without homelessness, without illness. But zero isn't good. It's stasis. The question that unlocks genuine systems change isn't 'how do we end this bad thing?' It's 'what does a healthy, equitable, joyful community actually look like — and what will it take to create that?' Purpose-driven leaders who make this shift stop playing defence and start building something worth aiming at. The questions leaders ask determine the results organisations get Every thought is the answer to a question — including the questions we don't know we're asking. Conventional strategic planning asks 'what can we accomplish in the next two years?' or 'what can we get funded?' Those questions produce reactive, incremental plans. Catalytic Thinking asks 'what would our community look like if we were 100% successful?' — and that question produces a fundamentally different strategy. For purpose-driven leaders, the implication is significant: the questions you bring into your planning process are already shaping what's possible before anyone picks up a pen. Radical Inclusion: start by asking who isn't in the room The first question of Catalytic Thinking is: who will be affected by whatever we're considering, and what would it take for them to be part of the decision — or even to lead the direction we take? A 30-person strategic planning group making decisions that affect a million people isn't just inefficient — it's structurally designed to miss the most important knowledge available. Radical Inclusion is the opposite of target marketing: instead of narrowing your focus to who you think matters, you expand it to everyone who will be touched by your work. That shift, Hildy argues, is where love enters leadership. Money is not a resource — and reframing this unlocks abundance Money is a means of exchange for the things organisations actually need: information, expertise, relationships, space, vehicles, cooking facilities. When leaders jump straight to 'we need more funding,' they skip past the question of what they truly need — and miss the abundance that already exists in their community. Hildy calls this Collective Enoughness: together, we already have everything we need. It's only when organisations go it alone, in a scarcity mindset, that they experience lack. For nonprofit leaders and social entrepreneurs especially, this reframe changes how you approach partnerships, resource-sharing, and community engagement. Hope is a leadership practice, not a feeling In a world that feels like it's moving backwards, Hildy's challenge to purpose-driven leaders is direct: resist and react, yes — but simultaneously plan for the world you want. If all we do is play defence, we'll be playing defence forever. The current moment is part of a longer pendulum swing, and the organisations that will matter in 10 years are the ones building toward what's possible right now — not just protecting against what's wrong. Hope isn't wishful thinking. It's a practice rooted in concrete planning, causality-driven strategy, and the brain science that says creativity requires quieting the reactive, fear-driven part of the brain. RESOURCES MENTIONED Creating the Future (includes free weekly Catalytic Thinking exercises via newsletter) Hildy's forthcoming book: How to Create the Future (out late 2026) Hildy's TEDx Talk Hildy's article in Stanford Social Innovation Review: 'Creating a Better World Means Asking Better Questions' The Catalytic Thinking fact sheet: The 7 Questions The Creating the Future podcast Community Centric Fundraising movement CONNECT WITH HILDY Website: creatingthefuture.org Newsletter: creatingthefuture.org — sign up for free weekly Catalytic Thinking exercises Amazon: search 'Hildy Gottlieb' for full book list WORK WITH CAROLYN Carolyn Butler-Madden works with leaders and organisations on how purpose becomes a powerful driver of trust, performance, and resilience. She speaks at leadership conferences and company events about how purpose shows up where it matters most — in leadership, culture, and strategy — helping organisations grow with clarity and confidence in a changing world. Key
