Dig Deeper

Ever found yourself in a conversation where someone's perspective seems completely wrong to you? Where your first instinct is to correct them, challenge them, or prove your point? What if that instinct is actually blocking you from real connection and genuine influence?This solocast explores a powerful encounter on a flight that challenged everything about how we engage with differing viewpoints. You'll discover why everyone's perspectives make perfect sense to them, even when they seem completely at odds with your own beliefs. Understanding this changes everything about your ability to connect and lead.Through a candid story about a conversation on US politics and South Africa, I'll show you how curiosity beats critique every time, and why meeting people where they're at without judgment opens doors that argument slams shut. This isn't about agreeing with everyone – it's about expanding your own perspective and building the kind of understanding that creates real influence.You'll learn:Why your first instinct to correct someone's "wrong" viewpoint limits your leadershipHow to listen for understanding rather than listening to respondThe difference between proving your point and improving your viewpointWhy meeting people where they're at is essential for genuine connectionHow expanding your perspective gives you greater awareness of the complex world we're leading inPractical ways to ask questions that deepen understanding rather than create defensivenessWhy curiosity and judgment can't coexist – and which one actually creates influenceWhether you're navigating difficult conversations at work, trying to understand different perspectives in your community, or simply wanting to become a more effective communicator, this episode will shift how you approach every interaction where viewpoints differ.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/

What if the most courageous leadership decision you ever make isn't about charging forward, but about stepping aside? And what if the key to authentic influence isn't having all the answers, but mastering the paradox of deep confidence paired with genuine curiosity?This episode explores the delicate balance between ego and humility that defines transformational leadership. We dive deep into how brutal self-honesty can become your greatest strength, why emotional intelligence is no longer optional for leaders, and how creating space for others to contribute might be the missing piece in your leadership approach.Andrew Little is a figure who redefined political courage in New Zealand by making one of the gutsiest calls in the country's political history: resigning as Labour Party leader just weeks before an election to make way for Jacinda Ardern. A former union leader turned politician, Andrew brings a unique perspective on leadership forged through decades of navigating complex stakeholder relationships, from representing workers to serving as a cabinet minister. His journey from a conservative household to progressive leadership offers profound insights into how our views can evolve while our core values remain steadfast.You'll discover:How to balance confidence with  "wonderance": the art of remaining curious while holding firm convictionsWhy reading your opponents' views strengthens rather than weakens your positionHow to create psychological safety where no viewpoint is considered "dumb" and everyone has access to leadershipWhy the phrase "you're either there to make decisions or make friends" misses the point of collaborative leadershipHow to process significant setbacks without letting them derail your purpose or self-worthWhy showing appropriate emotion in leadership is a superpower rather than a weaknessHow to navigate opposing views by finding shared values and common groundWhy the question "what is the why?" becomes your most powerful tool for building understandingTimestamps:(00:00) - The Paradox of Leadership(11:18) - The Decision to Step Aside(14:39) - Processing Emotions in Leadership(20:44) - The Role of Collective Leadership(26:00) - Navigating Opposing Views(30:33) - The State of Leadership TodayOther references:1981 Springbok Tour in New ZealandAndrew Little resignation as Labour LeaderEngineering, Printing and Manufacturing UnionAndrew Little to run for Wellington MayoraltyYou can find Andrew at:LinkedIn: https://www.linkedin.com/in/andrewlittle-nz/Facebook:https://www.facebook.com/andrewlittlenz/ Instagram: https://www.instagram.com/andrewlittlenzBlueSky: https://bsky.app/profile/andrewlittlenz.bsky.socialX : https://x.com/andrewlittle_nzCheck 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/

Have you ever found yourself speaking at cross purposes with someone, searching for that elusive connection point that might unlock meaningful progress?What if the most powerful leadership practice isn't about getting straight to business, but about genuinely meeting people where they're at first?In this solocast episode, I share a story from Papua New Guinea that changed how I think about building trust and connection. When a head of HR literally threw my 360-degree feedback report in the bin, I had a choice: push harder or find another way in.What happened next taught me something profound about what I call "I-matter conversations" - those moments when someone feels truly seen and heard, not for what they can deliver, but for who they are.You'll discover:Why connection before content transforms resistance into opennessHow to recognise when someone needs to feel they matter before they'll engageThe power of patience and genuine curiosity when building relationshipsWhy investing time in "I-matter conversations" is leadership, not just nicenessHow small moments of authentic listening can unlock breakthrough conversationsWhether you're facing resistance from a team member, trying to build trust quickly, or simply wanting to create more meaningful connections in your leadership, this story will change how you approach those challenging relationship moments.Sometimes the longest route to getting things done is actually the shortest.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/

What if the very thing you think makes you qualified to lead is actually limiting your impact? And what if the version of leadership you've been trying to perfect isn't even yours to begin with?This episode explores how authentic leadership begins with claiming your own space to be you, rather than becoming a caricature of someone else's approach. We discover why recognising your agency isn't about gaining permission from others, but about remembering the power you already possess and learning to wield it with intention.Nicola Nation is the former CEO of the Ākina Foundation, a leader who at age seven wrote to her parish priest demanding girls be allowed to serve on the altar, with aspirations of becoming the first female pope. Her journey from that bold seven-year-old to a purpose-driven executive offers profound insights into how we can break free from the "should" and "have to" stories that constrain us. You'll discover:How shifting from obligation to desire transforms your leadership effectivenessWhy creating space for yourself actually creates space for others to thriveHow to recognise when you're operating from over-responsibility versus empowered choiceWhy being a "ruthless prioritiser" is essential for sustainable leadershipHow to identify and move through the fear that keeps you playing smallWhy "hell yeah, within a container" becomes your framework for big decisionsHow small friction changes (like logging out of LinkedIn) can reclaim your attentionWhy curiosity about others becomes a pathway to unexpected wisdomTimestamps:(00:00) - Introduction(10:24) - Transforming Leadership: From Should to Want(12:23) - Creating Space for Others and Yourself(14:42) - The Scary Journey of Being Yourself(26:40) - Navigating Life's Hell Years(30:07) - Embracing Fear and Opportunity(33:11) - The Journey to Purpose-Driven LeadershipOther references:Derek Sivers: https://sive.rs/n“Things You Can See Only When You Slow Down: https://www.amazon.com/Things-Only-When-Slow-Down/dp/0241298199Kaitoke Regional Park: https://www.gw.govt.nz/parks/kaitoke-regional-park/Andrew Maffet: https://dig-deeper.captivate.fm/episode/4-the-power-of-being-unhurried-what-happens-when-you-dial-up-curiosity-and-what-leadership-is-really-about-andrew-maffett/Simon Dowling: https://dig-deeper.captivate.fm/episode/18-why-creating-space-matters-more-than-efficiency-simon-dowling-on-intentional-leadership/You can find Nicola at:LinkedIn: https://www.linkedin.com/in/nicola-nation/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/

What if the secret to finding your place in any new situation isn't about making a big first impression, but about the quiet power of simply showing up, again and again? And what if the discomfort you feel when you're the outsider is actually the gateway to genuine connection?This solocast explores the profound simplicity of consistency – how regular presence creates familiarity, familiarity builds trust, and trust opens doors you didn't even know existed. Through personal stories from a new neighbourhood café and a windsurfing beach in New Zealand, you'll discover why being a reliable presence comes before becoming a significant one.Drawing on the psychological principle of the ‘mere exposure effect’, I'll show you how exposure over time naturally creates preference and connection. This isn't about networking tactics or forced relationship-building – it's about the patient art of becoming part of the energy of what's already happening around you.You'll learn:Why the discomfort of being "new" is actually where real connection beginsHow consistency creates opportunity in ways that one-off efforts never canThe difference between being a reliable presence and a significant one – and why sequence mattersHow the mere exposure effect works in boardrooms, communities, and anywhere you want to belongWhy authentic persistence beats impressive entrances every timeThe art of joining the flow rather than forcing your way inHow to bring your authentic self into spaces regularly without being overbearingWhy patience with the process is essential for real connectionWhether you're starting a new job, joining a new team, moving to a new community, or trying to create change in your organisation, this episode will shift how you think about showing up and finding your place.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/

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/

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/

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 https://www.linkedin.com/in/digbyscott/

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/

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 at:Website: https://www.cultivatingleadership.com/ LinkedIn: https://www.linkedin.com/in/jennifer-garvey-berger-7b4a264/Books: "Unlocking Leadership Mind Traps," "Simple Habits for Complex Times," and "Changing on the Job"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/