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• 26. Breaking Out of ‘Answer Mode’, Building Collective Wisdom, and the Village That Raises Leaders | Kirsten Patterson

  What if the question isn't "Where are all the leaders?" but "Where are all the responsible adults?"Today I'm joined by Kirsten Patterson, better known as KP, CEO of the Institute of Directors New Zealand and chair of the Global Network of Directors Institutes.She had an auspicious start by getting suspended from school at five for challenging the system. Yet she went on to become one of New Zealand's most respected governance leaders. In 2025 she was awarded the New Zealand Royal Honour, Member of the New Zealand Order of Merit for her services to governance and women in leadership, She’s also known for her work founding multiple diversity initiatives including Chapter Zero New Zealand, which focuses on climate governance.KP's background includes growing up in a funeral home, giving her a unique perspective from observing how humans show up during challenging times, and what actually matters when the chips are down. She's built her reputation on asking the curly questions others avoid in a world that’s chasing answers.We explore how wonder and curiosity might be the antidote to our crisis-driven world, why asking questions we don't know the answers to is a lost art, and how creating space for reflection isn't a luxury – it's essential for responsible leadership.Whether you're wrestling with uncertainty or seeking to lead with more depth and authenticity, this conversation will challenge how you think about what it means to be a grown-up in today's world.Timestamps:(00:00) - The Chocolate Fish Test: Questioning Leadership(02:10) - Where Are the Responsible Adults?(10:53) - Balancing Confidence and Wonderance(21:00) - The Role of Wonder in Leadership(34:28) - Personal Journey: From Funeral Home to Leadership(41:54) - Collective Responsibility in Developing LeadersOther references:Institute of DirectorsSusan Cain - TED TalkSusan Cain - “Quiet” bookWellington Homeless Women’s TrustWellington City MissionCranlaner FoundationKate Christiansen - The Answer Trap Book - Not yet releasedJames Miller EpisodeYou can find Kirsten at:Website: https://www.iod.org.nz/LinkedIn: https://www.linkedin.com/in/pattersonkirsten/Check out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

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• 25. What If Resistance Is a Signal, Not a Problem?

  What if resistance isn't something to overcome, but something to work with? And what if that uncomfortable tension you feel when facing change is pointing you toward something valuable on the other side?This solocast dives into the emotional messiness of change through the lens of a recent house move. It’s one of life's most stressful transitions. You'll discover how loss aversion creates natural tension between holding onto what we treasure and stepping into the unknown, and why this tension is is feature, not a bug, in the system..Through honest reflections on leaving my much-loved home for a fresh start, I'll share three practical approaches that helped navigate the interior world of transition. This isn't just about personal change – these insights translate directly into how you can lead your team through organisational shifts, restructures, and new directions.You'll learn:Why resistance is a signal pointing toward possibility, not an obstacle to eliminateHow loss aversion affects our ability to embrace change – and what to do about itThe power of being in motion and creating meaningful involvement during transitionsWhy acknowledging the full range of emotions speeds up the change processHow to lean into the new while honouring what you're leaving behindThree practical strategies for leading your team through change without fighting their resistanceWhy showing what's now possible matters more than pushing people to let goHow to create non-judgmental spaces for people to process transitionWhether you're facing personal change, leading organisational transformation, or simply wanting to get better at navigating life's inevitable shifts, this episode will change how you think about resistance and what lies on the other side of it.I also mention Jason Clark's "Four Doors of Change" tool. Check that out here: https://www.youtube.com/watch?v=vPhM8lxibSUCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

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• 24. The Man Behind the Microphone, Unhurried Productivity, and the Power of ‘I-Matter’ Conversations | Digby Scott

  What if your perception of "unhurried productivity" isn't about someone constantly on holiday, but rather a deliberate approach to crafting a life aligned with your values?And what if the most powerful leadership practice isn't about getting things done faster, but creating genuine I-matter conversations where people truly feel seen and heard?That's what emerges in this special episode of Dig Deeper, where the tables are turned as I step into the guest chair of my own podcast. My friend Antonia Milkop takes the host role, guiding a conversation that explores the person behind the mic.We get into:Why "meeting people where they're at" transforms resistance into meaningful connectionHow burnout at 30 led to a complete reevaluation of my approach to life and workThe distinction between being "nice" versus being "kind" in leadershipWhy connection before content is the foundation of trust in any relationshipHow unhurried productivity is a state of mind, not just a state of movementWhy pivotal moments with "tough love" mentors can shape our leadership journeyHow embracing discomfort and messiness might be the gateway to our most significant growthWhether you're wrestling with busyness, curious about building trust quickly with new teams, or simply interested in the philosophy behind Dig Deeper, this conversation offers a glimpse behind the curtain that might change how you think about creating space for what truly matters.In this role-reversal episode, Antonia skillfully draws out perspectives on my journey from being a people pleaser to someone who stands for something, and why focusing on intentionality rather than constant activity leads to more meaningful outcomes.Timestamps:(00:00) - Introduction(05:16) - The Importance of Intentionality (12:09) - Pivotal People and Moments in Life(15:32) - Building Trust in Leadership(23:40) - The Power of Connection Before Content(36:27) - Unhurried Productivity: Finding Balance in Busy Lives (41:02) - Embracing Discomfort and Uncertainty in LeadershipYou can find Antonia at:LinkedIn: https://www.linkedin.com/in/antoniamilkop/Others mentioned:Cam Fink: https://www.camfink.com/Simon Dowling: https://dig-deeper.captivate.fm/episode/18-why-creating-space-matters-more-than-efficiency-simon-dowling-on-intentional-leadershipGeorgia Murch: https://georgiamurch.com/Jennifer Garvey Berger: https://www.cultivatingleadership.com/team-member/jennifer-garvey-bergerAdam Cooper: https://dig-deeper.captivate.fm/episode/14-natural-systems-nervous-systems-and-navigating-change-adam-cooperCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn

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• 23. How to Bring Both Your Head and Heart to Leadership

  Ever found yourself so focused on getting things done that you've completely disconnected from what you're feeling? And noticed how that numbness starts seeping into your relationships, your team dynamics, and your ability to truly lead?This episode explores the critical balance between head and heart in leadership – and why operating from just one without the other is limiting your impact. You'll discover how emotional disconnection during high-pressure periods can undermine everything you're trying to achieve, and more importantly, how to reconnect in ways that enhance both your effectiveness and your humanity.In this solo episode, I share my experience of emotional disconnection during a recent transition and how it affected my leadership. I explore the stark differences between head-only and heart-centred leadership approaches, and I share some practical steps to integrate emotional awareness into your leadership practice without sacrificing results.You'll learn:Why numbness in one area of life inevitably affects your leadership effectivenessHow to recognise when you're operating purely from the head versus connecting with heartThe difference between task-focused and emotionally intelligent leadership responsesPractical ways to schedule "heart time" and celebrate wins that create deeper team connectionHow vulnerability and courage become essential tools for authentic leadershipWhy connection becomes even more crucial during tight deadlines and high-pressure periodsCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

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• 22. Embracing Confusion, The Power of Idealism, and Cultivating a Well-Lived Life | Jennifer Garvey-Berger

  Do you find yourself constantly seeking clarity and certainty, even when faced with complex challenges that don't have simple answers? What if that very pursuit of certainty – that comfortable feeling we all chase – is actually blocking your growth, your learning, and your ability to create something new?This episode explores the counterintuitive idea that confusion isn't something to avoid, but rather something to value as a gateway to deeper learning. What's possible when we release our grip on needing to know and instead embrace the generative space of uncertainty? Together we consider how the most meaningful growth often happens precisely when we're willing to step into discomfort rather than rushing to make it disappear.Jennifer Garvey-Berger is a thoughtful disruptor who's constantly questioning how we might do business, relationships, family, and leadership better. As CEO of Cultivating Leadership, she's spent decades helping leaders navigate complexity and uncertainty. Jennifer brings a fascinating blend of intellectual rigor and lived experience to our conversation, including her bold experiment of buying a house with twelve friends in France to deliberately create a different way of living. In this episode, you'll discover:How confusion serves as a necessary gateway to learning and growthWhy certainty, despite feeling comfortable, often blocks our ability to discover new possibilitiesHow good conversations create something neither person had thought of beforeWhy crafting a meaningful life requires questioning default assumptionsHow deliberate disruption can lead to more authentic ways of working and livingWhy play and exploration remain essential elements of leadership at any ageHow creating intentional communities can challenge our assumptions about work/life separationWhy our idealism is not something to outgrow but rather a strength to cultivateTimestamps(00:00) The Value of Confusion(08:47) The Quest for a Better World(14:55) Living Fully vs. To-Do Lists(32:18) Creating a Unique Living Environment(40:03) Growth Through Difficulties(42:28) Giving Less FucksOther references:David Whyte: https://www.goodreads.com/quotes/9100423-what-you-can-plan-is-too-small-for-you-toRichard Bach: https://en.wikipedia.org/wiki/Illusions_(Bach_novel)Oliver Burkeman: https://en.wikipedia.org/wiki/Four_Thousand_Weeks:_Time_Management_for_MortalsVito Perrone: https://www.gse.harvard.edu/ideas/news/11/09/hgse-remembers-vito-perroneThomas Huebl: https://thomashuebl.com/Heidi Brookes: https://www.cultivatingleadership.com/team-member/heidi-brooksAndrew Maffett: https://player.captivate.fm/episode/8dc40ef3-104d-4a48-a38e-495ed4650abbAdam Cooper: https://player.captivate.fm/episode/48bf4ecf-f533-47d3-943e-2445135d473dYou can find Jennifer...

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