

Dig Deeper
Digby Scott
There's no one way to lead. Yet we need to find a way. Our own way. And it can be hard to get right. As we find our way to lead it can be useful to listen to how others found theirs.
Each fortnight, I’ll share a rich, unhurried conversation with someone who’s leaned into and learned from the challenges of leadership, change, and life while staying true to themselves.
You'll get to experience me doing what I do best: asking the surface-piercing questions to help people see what they couldn't see before. Including you.
Learn more about my courses and get more resources at https://www.digbyscott.com/
And follow me on LinkedIn here: https://www.linkedin.com/in/digbyscott/
Each fortnight, I’ll share a rich, unhurried conversation with someone who’s leaned into and learned from the challenges of leadership, change, and life while staying true to themselves.
You'll get to experience me doing what I do best: asking the surface-piercing questions to help people see what they couldn't see before. Including you.
Learn more about my courses and get more resources at https://www.digbyscott.com/
And follow me on LinkedIn here: https://www.linkedin.com/in/digbyscott/
Episodes
Mentioned books

Sep 15, 2025 • 6min
37. When Leadership Feels Like Swimming Upstream
Feeling burnt out and overwhelmed by constant change? You're not alone, and more importantly, you're not broken. In this thought-provoking episode, Digby explores the paradox at the heart of modern leadership challenges: how the problems we face are both completely beyond our control and entirely within it.Drawing on Viktor Frankl's timeless wisdom about choosing our attitude in any circumstance, Digby unpacks why structural forces often feel insurmountable and how brilliant leaders get trapped thinking they just need to push harder. Through the powerful metaphor of swimming against a fast-flowing river, he reveals the hidden choices available to us even in the most challenging situations.You'll discover the difference between external structural forces (like organisational culture and economic pressures) and the internal ones we carry within us (our assumptions, beliefs, and the stories we tell ourselves). Most crucially, you'll learn how shifting from being subject to change to becoming an agent of change can transform both your leadership and your wellbeing.Whether you're a CEO feeling the weight of responsibility or anyone navigating complexity and burnout, this episode offers a fresh perspective on finding your way to the riverbank when the current feels too strong.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/

Sep 8, 2025 • 51min
36. Stepping Into Visibility, Reading the Room, and Why Leadership Isn't About Being Perfect | Cam Fink
What if the very thing that makes you uncomfortable about being seen is exactly what's holding you back as a leader?Today I'm walking by the ocean and sitting in a Wellington playground with Cam Fink, a videographer who's spent years on the other side of the lens, observing what happens when leaders step into visibility.We explore why being comfortable on camera isn't really about cameras at all – it's about your willingness to be authentically seen. Cam shares what he's learned about energy, presence, and human connection from filming thousands of people, and why the skills that make you compelling on video are the same ones that make you an engaging leader.Whether you're leading a team meeting or recording your first LinkedIn video, this conversation will change how you think about showing up authentically in any situation where you need to influence and inspire others.Cam Fink is a videographer, director, and the creator of the brilliantly named course "Be Less Shit on Camera." He's also my go-to person for helping me feel comfortable and confident whenever there's a camera pointed in my direction.Timestamps:(00:00) - The Need for Human Connection(06:02) - The Role of Energy in Leadership(17:47) - Visibility and Connection in Leadership(24:51) - Shifting from Bystander to Activator(32:11) - Embracing Authenticity and Vulnerability(36:12) - Navigating Negative Feedback and Self-PerceptionOther references:Santo, Sam and Ed's Cup FeverSanto CilauroThe CastleThought Leaders Business SchoolPeter CookMatt ChurchCol FinkTony WilsonSimon DowlingYou can find Cam Fink at:Website: https://www.camfink.com/LinkedIn: https://www.linkedin.com/in/camfink/Course: https://www.camfink.com/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/

Sep 1, 2025 • 6min
35. How Are You Creating Lasting Impact?
What if the constant firefighting and crisis management that fills our days is actually stealing our chance to create something truly meaningful? And what if the most important work we can do isn't about solving the next problem, but about building something that lasts well beyond our time here?This episode explores how we can shift from reactive mode to creating lasting impact. Drawing from fresh insights gathered during 10 weeks of travel across five countries, Digby shares three powerful examples of enduring legacy: 3,500-year-old Bronze Age buildings in Sardinia that still stand strong, Royal Designers whose creations continue to enrich our lives decades later, and a volunteer marine rescue service that's been saving lives for over four decades.You'll discover why our modern culture of constant change and precious time traps us in reactive patterns, how to lift your head above the daily fires to focus on what truly matters over the long term, and practical ways to start building your own lasting impact today. Whether you're leading a team, running an organisation, or simply seeking to create something meaningful, this conversation will challenge you to think differently about the legacy you're creating.This episode marks the beginning of a deeper exploration into what it takes to lead lasting impact and offers a glimpse into new services designed to help senior leaders focus on creating enduring change.You’ll explore:Travel as a catalyst for fresh perspectivesThree examples of lasting impact: buildings, design, and serviceWhy reactive mode steals our chance for lasting impactQuestions to consider for your own lasting legacyCheck 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/

Aug 25, 2025 • 48min
34. Choosing Kind Over Nice, Disagreeing Well, and the Art of Courageous Connection | Georgia Murch
What if the conversations we're avoiding at work are exactly the ones that could transform everything?And what if there's a crucial difference between being nice to people and being truly kind to them – one that could revolutionise how you lead?Today I'm joined by Georgia Murch, founder of Can We Talk and someone who's spent over 25 years mastering what she calls "the dance" of building better cultures. Georgia's take is that most of us have lost the art of disagreeing well, and she's got some fascinating insights about why we're so conflict-avoidant – and what's possible when we learn to push through that discomfort.We explore why people hear your content but smell your intent, how to move from being a "magpie" or a "mouse" in conflict to becoming more like a "meerkat," and the surprising business impact of developing a solid meditation practice.Whether you're tiptoeing around difficult conversations or wondering how to create psychological safety while still holding people accountable, this conversation will change how you think about the courage required to truly serve others.Timestamps:(00:00) - The Difference Between Nice and Kind(17:51) - The Art of Disagreeing Well(27:09) - Embracing the Meerkat Within Us(31:38) - Meditation as a Tool for Clarity(34:50) - Leading with Freedom and Authenticity(43:03) - The Opportunity Beyond Conflict AvoidanceOther references:Brené Brown - “Dare to Lead”Thought Leaders Business SchoolThe Rest is Politics PodcastJennifer Garvey-Berger EpisodeAdam Cooper EpisodeYou can find Georgia at:Website: https://canwetalk.coLinkedIn: https://www.linkedin.com/in/georgiamurch/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/

Aug 18, 2025 • 3min
33. What’s Your Commitment to Yourself?
What if the clarity you're seeking isn't about having all the answers, but about cultivating deep conviction in what matters most to you?And what if the wobbly feeling you have when charting your own course isn't a sign you're on the wrong path, but evidence you're choosing authenticity over easy?In this solo episode, I reflect on a conversation that sparked some deep thinking about conviction and direction. Someone who knew me 25 years ago remembered my clarity of purpose during a time when I was actually feeling quite wobbly and uncertain. It got me wondering about the difference between confidence and conviction, and why one matters more than the other for sustained leadership impact.You'll explore:How major burnout at 32 led to life-changing clarity about what truly matteredWhy conviction can grow even when confidence feels shakyThe questions that form the foundation of authentic commitment to yourselfHow blind alleys and course corrections actually strengthen your sense of directionWhy comparing yourself to others' corporate trajectories misses the point entirelyThe relationship between authentic living and sustained impactHow to honour your values even when the path feels uncertainWhether you're questioning your current direction, feeling the strain of relentless effort, or simply curious about what it means to stay true to yourself over decades, this conversation offers a framework for cultivating the kind of conviction that becomes fuel for meaningful change.Sometimes the path that feels most uncertain in the moment becomes the only path that could have been truly yours. This episode explores why that paradox might be exactly what your leadership journey needs.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/

Aug 11, 2025 • 53min
32. Escaping the ‘Answer Trap’, and Why Slowing Down Speeds You Up
Kate Christiansen, a cognitive detective and author of "The Answer Trap," helps leaders enhance their thinking. In this discussion, she dives into the concept of the 'Answer Trap,' revealing how quick answers can stifle deeper understanding. Kate emphasizes the psychological effects of disruption, the dangers of relying on autopilot thinking, and the importance of curiosity in conversations. She advocates for slowing down to improve decision-making and fostering richer dialogues, urging us to embrace complexity rather than seek immediate closure.

Aug 4, 2025 • 4min
31. Everyone's Viewpoints Make Sense to Them: Why Listening Beats Arguing Every Time
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/

Jul 28, 2025 • 40min
30. Letting Others Shape the Vision, Curiosity Over Certainty, and Why Leadership Isn't About You | Andrew Little
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/

Jul 21, 2025 • 5min
29. Meeting ‘Em Where They're At: Connection Before Content
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/

Jul 14, 2025 • 51min
28. Claiming Your Space, Breaking Free from ‘Should’ Stories, and the Courage to Be You | Nicola Nation
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/