Dig Deeper

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:

1. Animal Liberation Orchestra
2. Deep Listening: Impact Beyond Words by Oscar Trimboli
3. Deep Listening Quiz

You can find Oscar at:

Website: oscartrimboli.com

LinkedIn: linkedin.com/in/oscartrimboli

Take the Deep Listening Quiz: listeningquiz.com

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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:

1. The hidden cost of trying to prove your worth through constant intervention
2. Why backing yourself changes everything about how you show up
3. What sustainable leadership actually looks like in practice
4. How to create conditions for others to succeed rather than being the sole hero
5. The shift from individual heroics to building systems that thrive
6. Why true leadership effectiveness is measured by the capability you build in others

Check out my services and offerings: https://www.digbyscott.com/

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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:

1. How authentic human stories serve as the antidote to AI-generated content that lacks heart and feeling
2. Why the most powerful cultural change happens when leaders let stories do the heavy lifting, rather than always being the storyteller themselves
3. How the practice of presence—whether watching wildlife or protecting creative time—becomes a discipline that sustains meaningful work
4. Why success might be better defined as freedom of choice rather than conventional measures of achievement
5. How stories create lasting impact by living in organizational culture long after the storyteller moves on
6. Why flipping the switch immediately can be more liberating than gradually planning for change
7. How leaders can spot when they're needed versus when they need to focus on what only they can do
8. Why 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:

1. Story Intelligence by Gabrielle Dolan
2. Sapiens: A Brief History of Humankind by Yuval Noah Harari
3. "Maker's Schedule, Manager's Schedule" by Paul Graham
4. National Australia Bank (NAB)
5. Bermagui, New South Wales, Australia
6. Dig Deeper Episode 20 with Sarah Manley
7. Dig Deeper Episode 32 with Kate Christiansen
8. The Answer Trap by Kate Christiansen

You can find Gabrielle at:

Website: https://gabrielledolan.com/

LinkedIn: https://www.linkedin.com/in/gabrielledolan/

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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:

1. Why leadership exists in the dynamic space between stability and change
2. How the ocean's unpredictability mirrors the challenges leaders face
3. What the intertidal zone teaches us about thriving in uncertainty
4. The challenges that come with leading from the edge (and why they're worth it)
5. Why awareness of patterns matters more than trying to control outcomes
6. How creating conditions for new ideas is more powerful than forcing solutions
7. Reflective questions to guide your own leadership development
8. What it means to be a lighthouse keeper in your leadership

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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:

1. How a simple shift in language from "my" to "our" transforms everything about how teams show up and support each other
2. Why creating permission for your team to not be busy all the time might be the most productive thing you do as a leader
3. How 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 team
4. Why determination matters more than having a clever strategy when you're trying to create momentum
5. How reading Harvard Business Review in the office was "frowned upon" but essential for Colin's growth as a leader
6. Why the most productive teams are often the least hurried—and what Colin did in 2008 to create that culture
7. How burnout at 31 became the catalyst for building an integrated life where work is part of the whole, not the whole itself
8. Why 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

1. On the Road Jack Kerouac - https://www.penguin.co.nz/books/on-the-road-9780241951538
2. Harvard Business Review - https://hbr.org/
3. Michael Page - https://www.michaelpage.co.uk/
4. Liverpool Echo - https://www.liverpoolecho.co.uk/
5. Camp America - https://www.campamerica.co.uk/
6. Abel Tasman Coast Track - 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/
7. Ronnie Scott’s Jazz club - https://www.ronniescotts.co.uk/
8. Everton Football Club - https://www.evertonfc.com/

You can find Colin at:

Website:https://www.colinellis.com

LinkedIn:https://www.linkedin.com/in/colindellis

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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:

1. Why curiosity by itself isn't enough, and the one action that turns wondering into wisdom
2. The crucial difference between knowing what to do and understanding when to do it (and when not to)
3. How shifting from hero to host leadership creates sustainable impact and brings out the best in your team
4. Why 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.

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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:

1. Why the partnership track in professional services can become a trap rather than a destination, and how to recognise when you're caught in it
2. How to shift from physical presence to emotional presence in both work and family life
3. Why redefining success requires asking what truly sustains you rather than what society says you should achieve
4. How professional training in law, accounting, or other demanding fields creates unexpected advantages in creative pursuits
5. Why being your own agent of change means not waiting for crisis to force your hand
6. How to navigate the guilt and fear of letting people down when walking away from senior positions
7. Why creating space for others to step up can reframe career transitions from selfish to generous acts
8. How the wrestle of expressing something in your own words makes us human in an age of AI

Other References

1. The Answer Trap Kate Christiansen
2. Humankind by Rutger Bregman
3. OpenAI
4. Bell Gully Law Firm
5. See 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:https://www.linkedin.com/in/rachel-paris-author

Check out my services and offerings https://www.digbyscott.com/

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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:

1. The four types of questions every leader needs to master: "what", "what is", "what if", and "what now"
2. Why "what" questions clarify focus and set the stage for meaningful dialogue
3. How "what is" questions help you uncover the real issues beneath the surface
4. Why "what if" questions ignite creativity and open up new possibilities
5. How "what now" questions drive action and accountability
6. A practical quadrant model you can use to structure any conversation
7. Simple techniques for naming shifts in your questioning to enhance clarity
8. Why 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

1. 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/
2. 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/
3. 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

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What if the secret to lasting leadership impact isn't about building your legacy, but about accepting that you're just passing through? And what if the shift from trying to prove yourself to truly backing yourself changes everything about how you show up as a leader?

This episode explores how moving from a hero mindset to a host mindset creates lasting change, and why focusing on embedded impact rather than personal legacy might be the most powerful leadership practice of all. We dive into the confidence that comes with experience, the urgency that emerges from accepting impermanence, and the art of creating solutions that endure long after you've moved on.

James McCulloch is the CEO of Victim Support New Zealand, where he's led one of the country's most remarkable organisational transformations. His perspective has been shaped by managing high-profile parks in the heart of London, navigating complex turnarounds, and now wrestling with the tension between ambition and balance as a seasoned leader. James brings a systems-aware approach to leadership that embraces both vulnerability and fierce determination.

You'll discover:

1. How to shift from needing external validation to backing yourself with genuine confidence
2. Why thinking of leadership roles as fixed-term rather than permanent creates productive urgency
3. How to build embedded solutions that create lasting impact beyond your tenure
4. Why moving from "my legacy" language to "our impact" transforms team dynamics
5. How vulnerability among leadership teams forges stronger bonds through adversity
6. Why the travelling CEO who over-promises creates more damage than help
7. How to balance the drive for meaningful impact with sustainable work-life integration
8. Why learning from your predecessors while avoiding the trap of constant comparison matters

Timestamps:

(00:00) - The Impact Over Legacy Mindset

(12:15) - Shifting from Proving to Backing Yourself

(21:11) - The Concept of Passing Through

(32:18) - Building Lasting Change: Strategies for Sustainable Impact

(37:58) - Balancing Ambition and Life: The Tension of Leadership

(43:11) - The Handover: Learning from Predecessors

Other References

1. We are all Fixed Term
2. Sir Ashley Bloomfield on When Leaders Are Human: Navigating Complexity With Integrity
3. Inspire Group
4. Jim Collins and Level 5 Leadership
5. International Coach Federation
6. International Parks Federation
7. Intercontinental Hotel Wellington
8. Guild Hall, London

You can find James at:

Website: https://victimsupport.org.nz/

LinkedIn: https://www.linkedin.com/in/james-mcculloch-65a2931b/

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/

What if the Christmas break you're desperately counting down to won't actually fix what's broken?

And what if the way we're running our years (like we run our cars, pushing hard until we desperately need a service) is the very thing keeping us stuck in this exhausting cycle?

In this solocast episode, I explore why most of us are caught in an infinite loop: work hard, get exhausted, take a break, repeat. We've all navigated some gnarly challenges this year, and it's tempting to think a few weeks off will sort everything out. But here's the truth: Christmas won't fix the underlying problems.

You'll learn:

1. Why the car metaphor for productivity is sabotaging your wellbeing
2. How tending a plant offers a better framework for sustainable work
3. The distinction between downtime and due time (and why both matter)
4. Why discovery is just as essential as delivery for doing your best work
5. How to reclaim more agency over your time than you might think
6. What it means to design your life with genuine intention
7. How leaders can create conditions where people actually thrive

Whether you're heading into the break feeling depleted, or you're curious about creating a more sustainable rhythm for 2026, this conversation will challenge how you think about rest, renewal, and what's actually possible when you shift from running your life to designing it.

This isn't about working less. It's about working differently. And it starts with questioning the beliefs we hold about productivity, downtime, and what it means to craft a life that's genuinely worth living.

Check out my services and offerings https://www.digbyscott.com/

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Life By Design Webinar: https://digbyscott.com/lifebydesign

How to Create Your Life By Design: https://digbyscott.com/thoughts/how-to-create-your-life-by-design

Unhurried Productivity: https://digbyscott.com/thoughts/fresh-insights-on-unhurried-productivity