Dig Deeper

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:

1. How to balance confidence with "wonderance": the art of remaining curious while holding firm convictions
2. Why reading your opponents' views strengthens rather than weakens your position
3. How to create psychological safety where no viewpoint is considered "dumb" and everyone has access to leadership
4. Why the phrase "you're either there to make decisions or make friends" misses the point of collaborative leadership
5. How to process significant setbacks without letting them derail your purpose or self-worth
6. Why showing appropriate emotion in leadership is a superpower rather than a weakness
7. How to navigate opposing views by finding shared values and common ground
8. Why the question "what is the why?" becomes your most powerful tool for building understanding

Timestamps:

(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 Today

Other references:

1. 1981 Springbok Tour in New Zealand
2. Andrew Little resignation as Labour Leader
3. Engineering, Printing and Manufacturing Union
4. Andrew Little to run for Wellington Mayoralty

You can find Andrew at:

LinkedIn: https://www.linkedin.com/in/andrewlittle-nz/

Facebook:https://www.facebook.com/andrewlittlenz/

Instagram: https://www.instagram.com/andrewlittlenz

BlueSky: https://bsky.app/profile/andrewlittlenz.bsky.social

X : https://x.com/andrewlittle_nz

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/

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:

1. Why connection before content transforms resistance into openness
2. How to recognise when someone needs to feel they matter before they'll engage
3. The power of patience and genuine curiosity when building relationships
4. Why investing time in "I-matter conversations" is leadership, not just niceness
5. How small moments of authentic listening can unlock breakthrough conversations

Whether 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/subscribe

Follow 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:

1. How shifting from obligation to desire transforms your leadership effectiveness
2. Why creating space for yourself actually creates space for others to thrive
3. How to recognise when you're operating from over-responsibility versus empowered choice
4. Why being a "ruthless prioritiser" is essential for sustainable leadership
5. How to identify and move through the fear that keeps you playing small
6. Why "hell yeah, within a container" becomes your framework for big decisions
7. How small friction changes (like logging out of LinkedIn) can reclaim your attention
8. Why curiosity about others becomes a pathway to unexpected wisdom

Timestamps:

(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 Leadership

Other references:

1. Derek Sivers: https://sive.rs/n
2. “Things You Can See Only When You Slow Down: https://www.amazon.com/Things-Only-When-Slow-Down/dp/0241298199
3. Kaitoke Regional Park: https://www.gw.govt.nz/parks/kaitoke-regional-park/
4. 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/
5. 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/subscribe

Follow 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:

1. Why the discomfort of being "new" is actually where real connection begins
2. How consistency creates opportunity in ways that one-off efforts never can
3. The difference between being a reliable presence and a significant one – and why sequence matters
4. How the mere exposure effect works in boardrooms, communities, and anywhere you want to belong
5. Why authentic persistence beats impressive entrances every time
6. The art of joining the flow rather than forcing your way in
7. How to bring your authentic self into spaces regularly without being overbearing
8. Why patience with the process is essential for real connection

Whether 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/subscribe

Follow 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 Leaders

Other references:

1. Institute of Directors
2. Susan Cain - TED Talk
3. Susan Cain - “Quiet” book
4. Wellington Homeless Women’s Trust
5. Wellington City Mission
6. Cranlaner Foundation
7. Kate Christiansen - The Answer Trap Book - Not yet released
8. James Miller Episode

You 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/subscribe

Follow 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:

1. Why resistance is a signal pointing toward possibility, not an obstacle to eliminate
2. How loss aversion affects our ability to embrace change – and what to do about it
3. The power of being in motion and creating meaningful involvement during transitions
4. Why acknowledging the full range of emotions speeds up the change process
5. How to lean into the new while honouring what you're leaving behind
6. Three practical strategies for leading your team through change without fighting their resistance
7. Why showing what's now possible matters more than pushing people to let go
8. How to create non-judgmental spaces for people to process transition

Whether 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=vPhM8lxibSU

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 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:

1. Why "meeting people where they're at" transforms resistance into meaningful connection
2. How burnout at 30 led to a complete reevaluation of my approach to life and work
3. The distinction between being "nice" versus being "kind" in leadership
4. Why connection before content is the foundation of trust in any relationship
5. How unhurried productivity is a state of mind, not just a state of movement
6. Why pivotal moments with "tough love" mentors can shape our leadership journey
7. How embracing discomfort and messiness might be the gateway to our most significant growth

Whether 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 Leadership

You 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-leadership

Georgia Murch: https://georgiamurch.com/

Jennifer Garvey Berger: https://www.cultivatingleadership.com/team-member/jennifer-garvey-berger

Adam Cooper: https://dig-deeper.captivate.fm/episode/14-natural-systems-nervous-systems-and-navigating-change-adam-cooper

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/

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:

1. Why numbness in one area of life inevitably affects your leadership effectiveness
2. How to recognise when you're operating purely from the head versus connecting with heart
3. The difference between task-focused and emotionally intelligent leadership responses
4. Practical ways to schedule "heart time" and celebrate wins that create deeper team connection
5. How vulnerability and courage become essential tools for authentic leadership
6. Why connection becomes even more crucial during tight deadlines and high-pressure periods

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

Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribe

Follow 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:

1. How confusion serves as a necessary gateway to learning and growth
2. Why certainty, despite feeling comfortable, often blocks our ability to discover new possibilities
3. How good conversations create something neither person had thought of before
4. Why crafting a meaningful life requires questioning default assumptions
5. How deliberate disruption can lead to more authentic ways of working and living
6. Why play and exploration remain essential elements of leadership at any age
7. How creating intentional communities can challenge our assumptions about work/life separation
8. Why our idealism is not something to outgrow but rather a strength to cultivate

Timestamps

(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 Fucks

Other references:

1. David Whyte: https://www.goodreads.com/quotes/9100423-what-you-can-plan-is-too-small-for-you-to
2. Richard Bach: https://en.wikipedia.org/wiki/Illusions_(Bach_novel)
3. Oliver Burkeman: https://en.wikipedia.org/wiki/Four_Thousand_Weeks:_Time_Management_for_Mortals
4. Vito Perrone: https://www.gse.harvard.edu/ideas/news/11/09/hgse-remembers-vito-perrone
5. Thomas Huebl: https://thomashuebl.com/
6. Heidi Brookes: https://www.cultivatingleadership.com/team-member/heidi-brooks
7. Andrew Maffett: https://player.captivate.fm/episode/8dc40ef3-104d-4a48-a38e-495ed4650abb
8. Adam Cooper: https://player.captivate.fm/episode/48bf4ecf-f533-47d3-943e-2445135d473d

You 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/subscribe

Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/

What if the most powerful thing you could do as a leader isn't to step in and save the day, but to step back and create space for others to shine? And what if your obsession with being the hero is actually preventing your team from reaching their potential?

This episode looks at one of the most challenging transitions in leadership: moving from hero to host. You'll discover why the traditional heroic model of leadership, where you're the one with all the answers, solving every problem, is unsustainable and ultimately limits both your impact and your team's growth.

I'll share practical insights on how stepping away strategically can enhance your leadership effectiveness, create self-sustaining systems, and build the kind of collaborative culture where everyone thrives. This isn't about becoming passive or disengaged. It's about becoming the kind of leader who creates ecosystems rather than dependencies.

You'll learn:

1. How to recognise when your heroic tendencies are holding your team back
2. The difference between stepping away and stepping out – and why timing matters
3. Practical strategies for creating psychological safety that allows others to step up
4. How to build sustainable systems that don't depend on your constant intervention
5. Why focusing on who you build is more important than what you build
6. Specific tools and approaches to make the hero-to-host transition successfully
7. How to celebrate team successes in ways that reinforce collaborative culture
8. The art of identifying opportunities to step back without losing momentum

Whether you're burning out from trying to be everything to everyone, or you're ready to create lasting impact beyond your direct involvement, this episode will reshape how you think about what leadership really means.

Download the Plan on a Page mentioned in this episode here: https://www.digbyscott.com/planonapage

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/