Dig Deeper

Digby Scott
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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/

  1. 50. Listening Beyond Words, and Choosing What to Say No To | Oscar Trimboli

    DEC 15

    50. Listening Beyond Words, and Choosing What to Say No To | Oscar Trimboli

    How much of what matters most are you missing while you're listening? Not the words themselves (you're good at capturing those) but what's underneath them, between them, beyond them.  Here's the uncomfortable truth: most of us believe we're better listeners than we actually are. We're busy preparing our response, managing the future, or distracted by the ping of the next urgent thing. Meanwhile, the people in front of us (the ones we're meant to be leading) are telling us everything we need to know. If only we knew how to truly hear it. In this conversation with Oscar Trimboli, we explore something deeper than communication skills. We venture into the territory of how we show up, what we say no to, and why the foundations we've already built might matter more than the future we're chasing. This is about the shift from hero to host, from infinite ambition to the surprising lightness of a ‘tour of duty’, and from listing ingredients to sharing the story of the meal. Oscar Trimboli is on a quest to create 100 million deep listeners in the workplace. He's spent decades discovering that the gap between speaking and listening isn't just about paying attention. It's about understanding that how we frame something can change what happens next. His work helps leaders see what they're missing when they focus only on the words. In this conversation, you'll discover: • Why the legacy you're creating might already exist in ways you can't yet see, and how acknowledging your past builds the foundation for what's next • How setting boundaries isn't about limitation but about the strategic clarity of knowing what you choose not to do • Why corporate funerals (literally burning what no longer serves) can create the trust that moves organisations forward when change initiatives get stuck • How the "tour of duty" mindset releases the weight of infinite responsibility and brings unexpected lightness to leadership • Why effective leaders operate as hosts rather than heroes, facilitating learning instead of performing expertise • How metaphors become mental shortcuts that help people understand the unfamiliar through the familiar, and why food and music work better than sport • Why distraction isn't just about devices but about the stories we tell ourselves when our attention wanders, and what choices we have in those moment • How "getting over yourself" enables you to serve the work rather than protect your ego, and why this shift makes everything else easier Timestamps: (00:00) - Introduction (06:39) - The Importance of Boundaries (10:32) - Navigating Change and Acknowledging the Past (19:11) - Corporate Funerals: Letting Go to Move Forward (24:41) - The Power of Rituals in Leadership (32:46) - Navigating Distractions in Conversations (42:59) - The Impact of Metaphors in Communication Other references: Animal Liberation OrchestraDeep Listening: Impact Beyond Words by Oscar TrimboliDeep Listening Quiz You can find Oscar at: Website: oscartrimboli.com LinkedIn: linkedin.com/in/oscartrimboli Take the Deep Listening Quiz: listeningquiz.com Check out my services and offerings a href="https://www.digbyscott.com/" rel="noopener noreferrer"...

    47 min
  2. 49. From Proving Yourself to Backing Yourself

    DEC 8

    49. From Proving Yourself to Backing Yourself

    Are you the bottleneck in your organisation? What if your greatest leadership contribution isn't solving every problem, but creating the conditions where others can thrive without you? I've been reflecting on a pattern I keep seeing in leaders—this constant pressure to prove our worth by being indispensable. Yet the organisations that truly transform are the ones where leadership doesn't depend on any single person staying in the room. This episode explores a fundamental shift: moving from proving yourself to backing yourself, and what that means for creating lasting impact. Drawing on insights from my conversation with James McCulloch, CEO of Victim Support New Zealand, I unpack what it takes to build systems that outlive your tenure, why organisations often reward heroics over sustainability, and how small, consistent choices can shift you from being the solution to creating the space where solutions emerge. You'll explore: The hidden cost of trying to prove your worth through constant interventionWhy backing yourself changes everything about how you show upWhat sustainable leadership actually looks like in practiceHow to create conditions for others to succeed rather than being the sole heroThe shift from individual heroics to building systems that thriveWhy true leadership effectiveness is measured by the capability you build in others 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/

    10 min
  3. 48. Authentic Storytelling and Creating Lasting Impact in an AI World | Gabrielle Dolan

    DEC 1

    48. Authentic Storytelling and Creating Lasting Impact in an AI World | Gabrielle Dolan

    What if the stories we're not telling are the very ones that could shape our organisations long after we're gone? In a world flooded with AI-generated content that sounds increasingly the same, I wonder what happens to the distinctly human act of storytelling. And here's the deeper question: are we waiting too long to make the changes that matter most? This conversation explores the enduring power of authentic human stories in an age of artificial intelligence, the gift of presence in our distracted leadership, and what becomes possible when we stop gradually planning and simply flip the switch. We're examining how stories don't just communicate culture—they are the culture, coursing through organisations like lifeblood, carrying meaning long beyond our tenure. What's emerging here is an invitation to reconsider where real impact lives and how it spreads. Gabrielle Dolan is one of the world's leading experts on storytelling in business, having spent over two decades helping leaders find their authentic voice and communicate with depth through story. She's the author of eight books, including her latest Story Intelligence, which she describes as the first she's felt truly compelled to write. After a health scare prompted her to abandon gradual retirement in favour of immediate life redesign, Gabrielle now spends her time between storytelling work she carefully selects, travelling, and watching kangaroos at her holiday property in Bermagui. In this episode, you'll discover: How authentic human stories serve as the antidote to AI-generated content that lacks heart and feelingWhy the most powerful cultural change happens when leaders let stories do the heavy lifting, rather than always being the storyteller themselvesHow the practice of presence—whether watching wildlife or protecting creative time—becomes a discipline that sustains meaningful workWhy success might be better defined as freedom of choice rather than conventional measures of achievementHow stories create lasting impact by living in organizational culture long after the storyteller moves onWhy flipping the switch immediately can be more liberating than gradually planning for changeHow leaders can spot when they're needed versus when they need to focus on what only they can doWhy knowing what a value means to you personally is essential before you can authentically communicate it to others Timestamps: (00:00) - The Role of Storytelling in an AI World (01:33) - Finding Presence in Nature (10:07) - Navigating Leadership Challenges (29:24) - The Art of Storytelling in Leadership (36:01) - The Enduring Nature of Stories (41:01) - Health Scares and Life Choices Other References: Story Intelligence by Gabrielle DolanSapiens: A Brief History of Humankind by Yuval Noah Harari"Maker's Schedule, Manager's Schedule" by Paul GrahamNational Australia Bank (NAB)Bermagui, New South Wales, AustraliaDig Deeper Episode 20 with Sarah Manleya...

    46 min
  4. 47. How to Lead from the Edge of Things

    NOV 24

    47. How to Lead from the Edge of Things

    What if the most dynamic leadership doesn't happen in the stable center or the chaotic unknown, but right at the edge between them? And what if trying to control everything is actually keeping you from discovering what's possible? In this solo episode, I explore leadership through the lens of the coast — that fascinating space where land meets sea. The intertidal zone, where stability and change collide, offers a powerful metaphor for the kind of leadership our complex world demands. I'll share why embracing the tension between control and adaptability isn't just necessary — it's where the most vital leadership occurs. You'll discover why the patterns you notice matter more than the predictions you make, how to navigate the loneliness that comes with leading at the edge, and what it means to be a lighthouse keeper who provides orientation rather than control. Whether you're feeling the pull between certainty and possibility, wrestling with forces you can't fully control, or simply curious about how to create the conditions for something new to emerge, this conversation will shift how you think about leading from the edge of things. In this episode, we explore: Why leadership exists in the dynamic space between stability and changeHow the ocean's unpredictability mirrors the challenges leaders faceWhat the intertidal zone teaches us about thriving in uncertaintyThe challenges that come with leading from the edge (and why they're worth it)Why awareness of patterns matters more than trying to control outcomesHow creating conditions for new ideas is more powerful than forcing solutionsReflective questions to guide your own leadership developmentWhat it means to be a lighthouse keeper in your leadership 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/

    12 min
  5. 46. Building Great Teams, Shifting from "My" to "Our", and the Power of Being Good Humans | Colin Ellis

    NOV 17

    46. Building Great Teams, Shifting from "My" to "Our", and the Power of Being Good Humans | Colin Ellis

    What if the very language you use—from "my target" to "our target," from "my client" to "our client"—is either building or breaking the culture you're trying to create? And what if being constantly busy is actually preventing the very work that matters most? In this conversation, I'm catching up with my mate Colin Ellis in a traditional English pub in Winchester. Colin's a five-time best-selling author and a super practical culture consultant who's spent decades helping organisations around the world rid themselves of what he calls toxic cultures. We're exploring the tension between delivering results and creating space for what actually sustains us—both as individuals and as teams and organisations. What emerges is a powerful reminder that building great culture isn't complicated. It's about creating the conditions where people can be good humans and do good work together. Colin Ellis grew up in Liverpool in a working-class family where security was paramount. After flunking school, he found his calling in project management—not for the technical side, but for the team-building aspect. His career took him from window cleaning family business roots to leading major project departments, from Melbourne to New Zealand and back to the UK. What's shaped his work most is his observation that the best teams valued both hard work and play, both productivity and camaraderie. He's built his reputation on making the complex simple, using language that connects with people who do the work day in, day out. His mission? To rid the world of toxic cultures by teaching leaders how to build great teams. You'll discover: How a simple shift in language from "my" to "our" transforms everything about how teams show up and support each otherWhy creating permission for your team to not be busy all the time might be the most productive thing you do as a leaderHow investing in relationships and camaraderie is as important as delivering on your targets—and why Friday drinks became sacred time for Colin's highest-performing teamWhy determination matters more than having a clever strategy when you're trying to create momentumHow reading Harvard Business Review in the office was "frowned upon" but essential for Colin's growth as a leaderWhy the most productive teams are often the least hurried—and what Colin did in 2008 to create that cultureHow burnout at 31 became the catalyst for building an integrated life where work is part of the whole, not the whole itselfWhy demystifying culture change is about using language people understand, not complicated frameworks Timestamps: (00:00) - Introduction (10.39) - Individualism vs. Teamwork (27:09) - Burnout and the Path to Change (35:27) - Creating Productive Work Environments (38:34) - Redefining Productivity (41:41) - Cultural Shifts in Work Dynamics Other References On the Road Jack Kerouac - https://www.penguin.co.nz/books/on-the-road-9780241951538Harvard Business Review - https://hbr.org/Michael Page - https://www.michaelpage.co.uk/Liverpool Echo - https://www.liverpoolecho.co.uk/Camp America - https://www.campamerica.co.uk/Abel Tasman Coast Track - a href="https://www.doc.govt.nz/parks-and-recreation/places-to-go/nelson-tasman/places/abel-tasman-national-park/things-to-do/tracks/abel-tasman-coast-track/" rel="noopener noreferrer"...

    49 min
  6. 45. Three Leadership Distinctions That Matter: Curiosity vs. Inquisitiveness, Knowledge vs. Wisdom, and Heroing vs. Hosting

    NOV 10

    45. Three Leadership Distinctions That Matter: Curiosity vs. Inquisitiveness, Knowledge vs. Wisdom, and Heroing vs. Hosting

    What if the gap between being curious and creating real change is just one small action? And what if the leadership move you've relied on your whole career is actually limiting your impact? This short episode cuts through the noise to explore three powerful distinctions that can transform how you lead. These aren't abstract theories. They're practical frameworks that help you navigate the messy, complex situations leaders face every day. You'll discover: Why curiosity by itself isn't enough, and the one action that turns wondering into wisdomThe crucial difference between knowing what to do and understanding when to do it (and when not to)How shifting from hero to host leadership creates sustainable impact and brings out the best in your teamWhy heroing might feel productive while hosting builds resilience, innovation, and genuine engagement This is a bite-sized episode designed for leaders who want practical insights they can apply immediately. Pick one distinction, experiment with it, and notice what shifts. Whether you're leading a team meeting, navigating uncertainty, or simply wanting to deepen your leadership practice, these three distinctions offer a fresh lens on what makes leadership truly impactful. 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/

    3 min
  7. 44. Freeing Up Your Future, Redefining Success, and the Courage to Begin Again | Rachel Paris

    NOV 3

    44. Freeing Up Your Future, Redefining Success, and the Courage to Begin Again | Rachel Paris

    What if the pinnacle of success you've been climbing towards is actually a trap? When you finally make partner, win the promotion, or achieve the milestone you've been chasing for years, what happens when you discover it's not the answer? When the very achievement that was supposed to bring freedom instead leaves you feeling like a rat in a mill, just surviving from one deadline to the next? This conversation explores what happens when we pause long enough to ask whether the life we're living is actually the life we want. Rachel Paris shares her journey from corporate law partnership to becoming a novelist, revealing how crisis can become catalyst, how the skills that made us successful in one domain become secret weapons in another, and why freeing up your future might mean letting go of the one you thought was already set. We get into the tension between security and creativity, physical presence and emotional presence, and what it truly means to redefine success on your own terms. Rachel Paris is a former partner at Bell Gully, one of New Zealand's most prestigious law firms, where she specialised in banking and finance for over a decade. After walking away from partnership, she became a bestselling novelist with her debut crime thriller "See How They Fall." Her sister's cancer diagnosis became the catalyst for change, prompting her to question whether surviving each day was any way to live a life. Rachel's journey from Harvard Law graduate to creative writer offers a fascinating lens on how professional skills translate across domains and what becomes possible when we give ourselves permission to begin again. You'll discover: Why the partnership track in professional services can become a trap rather than a destination, and how to recognise when you're caught in itHow to shift from physical presence to emotional presence in both work and family lifeWhy redefining success requires asking what truly sustains you rather than what society says you should achieveHow professional training in law, accounting, or other demanding fields creates unexpected advantages in creative pursuitsWhy being your own agent of change means not waiting for crisis to force your handHow to navigate the guilt and fear of letting people down when walking away from senior positionsWhy creating space for others to step up can reframe career transitions from selfish to generous actsHow the wrestle of expressing something in your own words makes us human in an age of AI Other References The Answer Trap Kate ChristiansenHumankind by Rutger BregmanOpenAIBell Gully Law FirmSee How They Fall by Rachel Paris Timestamps: (00:00) -  From Corporate Law to Creative Freedom (23:12) - Redefining Success and Embracing Change (27:07) - The Journey of Self-Discovery (29:24) - Navigating Career Transitions (32:11) - The Impact of Legal Training on Creativity (34:33) - Creativity in the Age of AI You can find Rachel at: Website: https://rachelparisauthor.com LinkedIn:a...

    47 min
  8. 43. The Four Questions That Transform Leadership Conversations: What, What Is, What If, and What Now

    OCT 27

    43. The Four Questions That Transform Leadership Conversations: What, What Is, What If, and What Now

    What if the quality of your leadership came down to the quality of your questions? And what if shifting just one word in how you frame a question could completely change the direction of a conversation? Most leaders ask questions to get answers. But the real power lies in asking questions that unlock thinking, creativity, and action in others. This episode introduces a practical framework for asking better questions – four simple categories that can transform how you lead meetings, drive strategy, and navigate complexity. Whether you're facilitating a team discussion, making a tough decision, or trying to move beyond surface-level conversations, these questioning techniques will shift what's possible. You'll discover: The four types of questions every leader needs to master: "what", "what is", "what if", and "what now"Why "what" questions clarify focus and set the stage for meaningful dialogueHow "what is" questions help you uncover the real issues beneath the surfaceWhy "what if" questions ignite creativity and open up new possibilitiesHow "what now" questions drive action and accountabilityA practical quadrant model you can use to structure any conversationSimple techniques for naming shifts in your questioning to enhance clarityWhy progression matters more than perfection when developing your questioning practice This is a short, practical episode designed to give you an immediately useful tool. The goal isn't perfection – it's progression. Pick one type of question, experiment with it in your next conversation, and notice what shifts. Whether you're preparing for a strategic discussion, wanting to deepen team engagement, or simply curious about how to facilitate better conversations, this framework offers a clear path forward. Related Episodes KP on Breaking Out of 'Answer Mode': https://dig-deeper.captivate.fm/episode/26-breaking-out-of-answer-mode-building-collective-wisdom-and-the-village-that-raises-leaders-kirsten-patterson/Kate Christiansen on Escaping the 'Answer Trap': https://dig-deeper.captivate.fm/episode/32-escaping-the-answer-trap-and-why-slowing-down-speeds-you-up/Simon Dowling on Why Creating Space Matters More Than Efficiency: https://dig-deeper.captivate.fm/episode/18-why-creating-space-matters-more-than-efficiency-simon-dowling-on-intentional-leadership/ The Questions Toolkit: digbyscott.com/questionstoolkit 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/

    13 min
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About

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/

Information

  • Creator
    Digby Scott
  • Years Active
    2024 - 2025
  • Episodes
    51
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Digby Scott
  • Show Website
    Dig Deeper

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