Dig Deeper

Digby Scott
Dig Deeper
Latest episode

71 episodes

  • Dig Deeper

    [Solocast] What Will Outlast You?

    25/05/2026 | 6 mins.
    You know how most days go. There's the list to clear, the email that just landed, the conversation that has to happen by Friday. You sort it, and tomorrow you do it all again. Those things matter, and I'm not going to pretend they don't. But if a good day's work is only ever solving the problems of that day, I reckon you're missing a trick. Because your days become your weeks, become your years. When you look back over those years, what will you be able to say you contributed? And what do you want to be able to say?
    This solocast came out of a briefing call with a school principal. She told me she'd been sitting in her own leadership team meeting, listening to everyone work through what needed doing, and quietly realised she didn't need to be there. She wasn't threatened by that. She felt good, like something had finally worked. We get into what makes that moment possible: the difference between a problem focus and a possibility focus, what shifts when you stop patching symptoms and start improving the system, and the language change that marks leaders who've started thinking beyond their own time in the chair, from "this is what I'm doing" to "how am I setting this place up to outlast me?"
    Here's some of what I cover:
    Why a possibility focus lifts your energy, while a problem focus has you tired and playing defence by Tuesday afternoon
    The shift from delegating tasks to genuinely growing the people around you
    Three questions we worked through at the conference, worth sitting with on a quiet morning
    How to find the intersection of where you're energised and where you're uniquely positioned to serve
    Why lasting impact asks you to choose one thing, not everything at once

    If relentless busyness is the pattern you keep running into, drop me a line at https://www.digbyscott.com/contact and we'll have a chat.

    Blog post https://www.digbyscott.com/thoughts/what-will-outlast-you/

    Check out my services and offerings https://www.digbyscott.com/
    Subscribe to my newsletter https://www.digbyscott.com/subscribe/
    Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
  • Dig Deeper

    [Interview] From Hero to Host, Letting Go, and Leading with Impact | A Dig Deeper Compilation

    18/05/2026 | 31 mins.
    There's something seductive about being the leader who walks into the room with the answers. Leadership culture has spent decades rewarding exactly that: the person who steps up, takes charge, and makes things happen. What if that pattern, the very thing that got you here, is also quietly limiting how far your people can go? And what if the most significant move available to you right now isn't to lead more, but to lead differently?
    This episode explores the shift from hero to host. It's one of those ideas that sounds deceptively simple and turns out to be one of the hardest things a senior leader can actually do. To mark a milestone in the Dig Deeper archive, five extraordinary guests are brought together, each of whom has found their own way into this idea. Through event design, pandemic leadership, organisational transformation, the craft of facilitation, and the quiet philosophy of letting go, they're all pointing at the same thing. I wonder what it would mean for your leadership if you took it seriously.
    These five voices shape the conversation. DK is a creative producer, speaker coach, and curiosity lightning rod who spent nearly a decade designing celebrated TEDx events in Wellington, known for an approach that starts with the people in the room, not the content on the stage. Sir Ashley Bloomfield served as Director General of Health for New Zealand through COVID-19, and discovered, sometimes painfully, that what people needed from their leader wasn't certainty. James McCulloch is CEO of Victim Support New Zealand, a leader who has quietly and deliberately refused to be the superhero the role invites him to become. Simon Dowling is a facilitator and author who has spent years helping leaders understand the spaces they create and why those spaces shape everything that becomes possible within them. Callum McKirdy is a coach and facilitator who makes a distinction between being, doing, and trying that might just change how you show up in your next meeting.
    From these five conversations, here's some of what you'll discover:
    How the shift from hero to host creates the conditions for lasting organisational change
    Why designing with your people in mind, rather than your agenda, changes everything
    How the distinction between legacy and impact reveals a fundamentally different kind of leadership
    Why kindness and niceness are not the same thing, and why that difference matters profoundly for teams
    How self-awareness is the foundation that everything effective leadership rests on
    Why the spaces a leader creates, intentionally or not, determine what becomes possible in those spaces
    How admitting what you don't know builds, rather than erodes, your credibility as a leader
    Why the word between "doing" and "being" is "trying," and what that costs us

    Timestamps:
    (00:00) From Hero to Host: A Leadership Paradigm Shift
    (06:55) The Power of Team Dynamics in Leadership
    (12:46) Legacy vs. Impact: Redefining Leadership Goals
    (19:00) Creating Intentional Spaces for Leadership
    (25:08) The Permission to Be: Authentic Leadership Practices
    Other references
    Ted Lasso
    Flawsome by Georgia Murch
    Jim Collins | Level 5 Leadership
    The Castle (1997)
    Tony Blair coming to power

    Connect with the guests:
    DK: Website
    Sir Ashley Bloomfield: LinkedIn
    James McCulloch: Website | LinkedIn
    Simon Dowling: Website | LinkedIn
    Callum McKirdy: Website | LinkedIn

    Check out my services and offerings https://www.digbyscott.com/
    Subscribe to my newsletter https://www.digbyscott.com/subscribe
    Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
  • Dig Deeper

    [Solocast] Fear: Name It, Frame It, Tame It

    11/05/2026 | 8 mins.
    Have you ever stood in front of a room with your heart thumping in your ears? Or walked away from a moment knowing you should have spoken up, and didn't?
    Fear runs more of our leadership than we like to admit. Powering through it works for a while, until it doesn't. Getting specific about what's actually going on underneath is where the real shift starts.
    In this solocast I share a three-part framework I've used for years to work with my own fear, especially before walking onto a stage: name it, frame it, tame it. It's simple, and it applies to all the everyday moments where the stakes feel higher than they probably are.
    Here's what I get into:
    The moment before I addressed a large audience for the first time, and what was actually running through my head
    Why putting words to a feeling changes what your brain does next
    The difference between fears that are about survival and fears that are about social standing
    Why the worst case version we play in our heads rarely shows up in real life
    A small action that builds more real confidence than another round of rehearsal
    Why naming your fears out loud builds trust with the people you lead

    References
    Fear - Name It Frame It Tame It worksheet
    Start Close In | David Whyte

    Check out my services and offerings https://www.digbyscott.com/
    Subscribe to my newsletter https://www.digbyscott.com/subscribe
    Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
  • Dig Deeper

    [Interview] Intergenerational Healing, Translation, and the Courage to Lead | Christian Penny

    04/05/2026 | 40 mins.
    What if the leadership model you've inherited is the very thing standing between your team and its potential? Most of us have experienced at least once what it feels like when a team is genuinely alive. When trust is in the room. When leadership moves around naturally, and people show up as their whole selves. And yet for most leaders, most of the time, the unspoken hope remains that the right person will arrive with the right answers and fix things. We race straight to task. We skip the human stuff. We declare a safe space and wonder why trust is still so hard to build, and so easy to lose.
    What if there's a fundamentally different way of meeting each other? One that's not just a nice idea, but a proven strategy for performance under the kind of pressure that matters most?
    In this conversation, Christian Penny brings a frame that has been tested across thousands of years on the marae and refined through decades of applying it in drama schools, Olympic programmes, and elite Super Rugby environments. It's a frame where presence and people come before task, not as an indulgence, but as the very investment that pays off when the pressure is on. Where leadership isn't a position but a question: what does this moment require, and who in the room can answer it? And where your distinct strengths, the things that only you bring, aren't optional extras but the contribution your team is quietly waiting for you to own.
    Christian Penny is one of New Zealand's most quietly radical leadership thinkers. A former Director of Toi Whakaari: NZ Drama School, co-architect of the Ruku Ao leadership programme for senior public sector leaders, and a current adviser to the Hurricanes Super Rugby team and the Black Ferns Sevens, Christian has spent his career asking a single question across wildly different performance contexts: what really creates the conditions where people and performance can thrive? Drawing on Māori frameworks, the craft of theatre, and years at the edge of elite sport, he brings a practice that bridges indigenous wisdom and contemporary leadership with uncommon depth and warmth.
    In this episode, you will discover:
    How the myth of the hero leader persists even when we know it doesn't work, and what the marae offers as a practical, tested alternative
    Why putting people before task isn't soft leadership, it's the investment that pays off under the most intense pressure
    How "go slow to go fast" transforms team performance precisely when it counts most
    Why alignment is often a fantasy, and how learning to use each other's difference is the real leadership skill
    How to ask the question that changes the room: "What does this moment require, and who can lead us here?"
    Why trust is emergent, not declared, and what that means for how you build it deliberately
    How knowing and naming your strengths doesn't just make you more potent, it makes life easier for everyone around you
    Why courage, not confidence, is the real prerequisite for stepping up, and how that reframe changes everything

    Timestamps:
    (00:00) - The Myth of the Hero Leader
    (10:25) - Presence Over Task in Leadership
    (17:26) - The Shift from Hero to Host Leadership
    (23:31) - Emergent Leadership and Dynamic Teams
    (30:01) - Overcoming Resistance to New Leadership Models
    (36:37) - The Importance of Small Victories in Leadership
    Other references:
    Toi Whakaari: NZ Drama School
    Ruku Ao leadership programme
    Manutūkē Marae, Rongowhakaata
    High Performance Sport New Zealand (HPSNZ)
    The Hurricanes
    Black Ferns Sevens
    Digby Scott's Superpowers exercise

    You can find Christian at:
    LinkedIn: https://www.linkedin.com/in/christian-penny-54016515/

    Check out my services and offerings https://www.digbyscott.com/
    Subscribe to my newsletter https://www.digbyscott.com/subscribe
    Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
  • Dig Deeper

    [Solocast] Put Down the Mallet

    27/04/2026 | 6 mins.
    You're across everything. The problems, the people, the pressure. And somehow, no matter how much you get through, there's always another thing popping up that needs your attention. Sound familiar?
    In this episode, Digby explores what it actually means to have a leadership identity and why most leaders are defining theirs by accident, one reactive moment at a time. Drawing on William James's observation that the ability to bring back a wandering attention is the very root of judgement and character, he makes the case that where you direct your focus is not a time management question. It's an identity question.
    In this episode, we cover:
    Why reactive leadership is like playing whack-a-mole and what it costs you over time
    The difference between solving problems and building the systems that make fewer problems inevitable
    How to define a leadership identity that guides your decisions before the pressure hits
    A practical exercise to help you name your purpose and start leading from it
    The one question that cuts through the noise: what do you need to build so your team can thrive without you?

    Check out my services and offerings https://www.digbyscott.com/
    Subscribe to my newsletter https://www.digbyscott.com/subscribe
    Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/
More Business podcasts
About Dig Deeper
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/
Podcast website

Listen to Dig Deeper, The Diary Of A CEO with Steven Bartlett and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features