What's your relationship like with discomfort? What about asking for feedback? Both of these things are essential to get our heads around if we're going to find our own way to lead and thrive in life.

This entertaining, thought-provoking conversation with Callum McKirdy will help you to become more comfortable with being uncomfortable. You’ll learn:

1. Why the fear of feedback stems from the disconnect between how we see ourselves and how others see us
2. How allowing people into our worlds and being vulnerable is the next big thing in breaking down barriers
3. How leadership is about facilitating an environment for others to bring their best and be their best (but not necessarily to be comfortable)
4. How letting go of control and embracing discomfort can lead to growth and new possibilities
5. That discomfort is not inherently bad; it can be a catalyst for self-reflection and change

You can find Callum at Website | LinkedIn

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Can we ever obtain a fully productive work life, or a fully productive organisation? What does that even mean? This rich conversation with impact coach and business consultant Danni Ermilova Williams will give you a fresh perspective on how to reshape work to create more meaningful, sustaining experiences.

Danni and I explore what it means to live and work well. We dig deep into how we put unseen limits in place and how we can create space for busting those limits for ourselves and our organisational cultures so we can get on with doing and being what matters most. We explore the idea of control versus surrender, and how the power of language can limit us, or open us up to new possibilities.

You can find Danni at Website | LinkedIn

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There's no one way to lead. Yet we need to find a way. Our way. That can be hard to get right. As we find our own way to lead it can be useful to listen to how others found theirs.

I'm your host, Digby Scott, leadership coach and author of Change Makers. I'm on a mission to help people find their authentic way to lead so they can have more impact with less drama. 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/

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"

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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

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Are you trying to make lasting change happen, but you feel like you’re banging your head against a wall of short-term dramas and siloed thinking?

This episode will help you to rise above the fray and hone in on how to be valuable, stay relevant, and play the longer game.

Dr. Richard Hodge is one of Australasia’s preeminent thought-leaders in systems thinking. He’s been in the workforce since 1970, with wide experience in science, engineering, public sector policy and the corporate world. Richard was one of the founding fathers of a major strategy business in Canberra, growing it to 80 staff and >$20M in revenue in 6 years. In 2007, he moved from advising GMs to being one in a global engineering business until he was sacked in 2010, one week after completing his PhD (part time). Since then, Richard has established his own practice helping leaders engage - not manage – complexity with the help of systems sciences.

Together, Richard and I dig deep into:

1. Why understanding value is crucial for effective leadership and decision-making
2. How relevance is determined by how well we align our actions with our values
3. How the long tail of consequences highlights the impact of our actions over time
4. Why community engagement is essential for sustainable change
5. The importance of efficiency not overshadowing ethics in organisational practices
6. How generational wisdom plays a crucial role in systems thinking
7. Why imagination is essential for envisioning change
8. How making small, incremental steps can lead to significant transformation
9. How defining 'enough' is vital for personal equilibrium.
10. Why connection and relationships are at the heart of effective leadership.

If you're looking for ways to have a more lasting and sustainable impact in your work and life, this episode will give you lasting pearls of wisdom.

Time Stamps:

(00:00) - Imagining Better Leadership Through Systems Thinking

(03:05) - The Dragonfly: A Metaphor for Leadership

(08:09) - Understanding Value, Relevance, and Long-Term Impact

(14:21) - The Role of Community in Effective Leadership

(21:38) - The Five E's of Leadership: Beyond Efficiency

(24:51) - Personal Stories Shaping Systems Thinking

(30:41) - Challenges in Implementing Systems Thinking in Organisations

(33:09) - Systems Thinking: The Spirit of Adventure

(35:37) - Imagination and Possibility Thinking in Leadership

(38:57) - The Long Game: Transformational Change in Organisations

(44:26) - Personal Growth: Applying Systems Thinking to Individual Development

(58:58) - Defining Enough: Values and Life Choices

You can find Richard at:

Website: https://www.drrichardhodge.com/

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

Article: Play the Long Game https://www.digbyscott.com/thoughts/play-the-long-game

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Do you feel like work is taking over your life, leaving little room for fulfillment? Are you struggling to make your work align with your values or wondering how to create more balance and purpose in your career?

In this episode, we explore how to bring more meaning into your work by aligning it with your values and learning how to lead with purpose. You'll hear how restructuring your approach to work can help you avoid burnout, create healthier boundaries, and make a lasting impact without sacrificing your well-being.

Gillian Brookes is an HR professional, consultant, and author of Flexperts, with a passion for creating workplaces that serve people, not just the bottom line. In this episode, we dive into:

1. How to redesign flexible work to create balance and well-being.
2. Why the current economic structure is leaving many people behind—and how we can change that.
3. The importance of boundaries and how to set them as a leader and working parent.
4. How to sustain your energy while maintaining conviction in your values.
5. What it means to create a purposeful and integrated life where work and personal values coexist.

You can find Gillian at:

Website: https://www.gillianbrookes.co.nz/

LinkedIn: https://www.linkedin.com/in/gillian-brookes-88928aa2/

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Have you ever felt uncertain about your career path or questioned whether your empathetic leadership style is a strength or a weakness?

Or maybe you’ve wondered if it’s okay to embrace a non-linear, “squiggly” career while still finding success and fulfillment.

In this episode, we dive deep into the power of following your gut, embracing a career that doesn’t follow the traditional path, and leading with vulnerability and empathy.

If you’ve ever worried about being ‘too nice’ as a leader, or if you’re facing burnout and wondering how to recharge, this conversation will help you uncover how to honour your values while carving your own path.

Jodi Willocks has a background in marketing and advertising. With 21 jobs in 26 years, she has a hugely diverse range of experiences that give her a unique perspective on leadership. She’s also a co-founder of the Women of Pōneke movement, and is an exquisite writer on leadership and career topics.

In our conversation, we explore:

1. Why empathy is a strength, not a weakness, in leadership
2. The importance of trusting your instincts and following a non-linear career path
3. How embracing vulnerability can unlock more authentic and effective leadership
4. What Jodi learned from leading through COVID and how it transformed her approach

Timestamps:

(00:00) - Introducing Jodi Willocks

(04:45) - The Foundation of Authentic Leadership

(10:05) - The Impact of COVID on Leadership

(17:54) - Navigating Career Breaks and Burnout

(28:58) - Discovering Creativity Through Blogging

(34:43) - The Importance of Recovery and Recharge

(42:58) - The Sanctuary, Sandpit, and Stage Framework

(50:13) - Ingredients for Successful Leadership

You can find Jodi at:

Website: https://www.careerjourneying.nz/

LinkedIn: https://www.linkedin.com/in/jodi-willocks-6b035446/

Women of Pōneke: https://www.womenofponeke.org.nz/

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In this final episode of Dig Deeper for 2024, I’m reflecting on the key themes I’ve explored in the podcast and my blogs throughout the year. I'll cover four themes:

1. the importance of discomfort for growth
2. the shift from a hero to a host mindset in leadership
3. the necessity of creating space for reflection
4. the power of letting go of control.

Each theme has insights from previous podcast guests and excerpts from my writing, and some questions for you to take away and reflect on.

Links:

Fire, by Judy Brown: https://www.judysorumbrown.com/blog/breathing-space

The Let Go: https://www.digbyscott.com/thoughts/the-let-go

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Do you ever feel hamstrung by the rules you’re bound by? The have-to’s and should’s and the ‘don’t-do-that’s’ that govern your work practices and broader life? Do you ever wonder what things would be like if you could change the rules of the game?

Rules are invented. They're made up. Which means they can be uninvented, or reinvented. Today’s conversation with behaviouralist and facilitator Suzanne Rosa explores the importance of identifying, challenging, and changing the rules to serve the purpose we’re here for.

After listening, you’ll have a fresh way of thinking about how you can unlock new ways of working and living to create more of what matters.

Suzanne was born in England and now lives in Sydney. She had a really tough upbringing: born deaf, she had multiple operations to restore her hearing. Then she lived in a truck travelling around Europe before becoming a foster child and then a homeless teenager. All of this led her to dig deeply into life's range of emotions and explore how we can utilise all that living has to offer. She's the author of two books, A Flourishing Mind, and Sleeping Giants. She can be summed up in three words: energy, curiosity, and ferocity.

In this conversation, we explore:

1. How our perception and lenses shape the meaning we make of the world
2. There is no one truth, and why it's important to question our own perspective
3. How societal conditioning often limits our ability to pioneer and think outside the box
4. How listening to our own signals and questioning the rules that hold us back can create conditions for a pioneering spirit
5. The importance of questioning societal norms and rules
6. How to take time to regather and ground yourself before embarking on new chapters of personal growth.

You can find Suzanne at:

1. Website: https://suzannerosa.com/
2. LinkedIn: https://www.linkedin.com/in/suzannewaldron/?originalSubdomain=au

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Join the Career Break community https://www.digbyscott.com/careerbreak

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

Leadership is a journey of constant tension – between expectation and authenticity, between comfort and courage, between being liked and being effective. What if you could transform those tensions into your greatest source of strength?

Join me for an extraordinary conversation with Sir Ashley Bloomfield, a leader who navigated one of the most challenging leadership landscapes in recent history. During New Zealand's COVID-19 response, he became the face of national resilience, embodying leadership under unprecedented pressure.

In this personal and candid episode, Sir Ashley pulls back the curtain on the raw, unfiltered realities of leadership. We'll explore the delicate balance between personal conviction and public expectation, the art of making tough decisions when the whole world is watching, and how to maintain your humanity while bearing immense responsibility.

In this episode, we dive deep into the heart of leadership, exploring:

1. Leadership as Inspiration: How an unexpected source – the beloved character Ted Lasso – provided unexpected wisdom during New Zealand's most challenging times
2. The Leadership Landscape: Navigating the complex terrain of modern leadership, from the rise of populism to the critical importance of empowering others
3. The Transformative Power of Agency: Understanding how true leadership is about creating space for others to act, not just directing from the top
4. The Courage of Vulnerability: Why saying "I don't know" is sometimes the most powerful leadership statement you can make
5. The Dangerous Allure of Simplicity: Unpacking why quick fixes and simplistic solutions can be more harmful than helpful in complex challenges
6. Adaptability as a Leadership Superpower: Exploring how continuous learning and flexibility are essential in our rapidly changing world
7. The Nuanced Art of Kindness: Discovering the critical difference between being "nice" and being truly kind in leadership
8. Decision-Making Decoded: Balancing the drive to be decisive with the wisdom of thoughtful, inclusive decision-making processes
9. Leadership Under Pressure: Understanding why personal conviction must often triumph over personal comfort
10. The Ripple Effect: How principled leadership can transform not just organisations, but entire communities

Get ready for a conversation that goes beyond traditional leadership advice – this is leadership unpacked, unfiltered, and deeply human.

These insights promise to challenge your understanding of leadership, offering a fresh, nuanced perspective that goes beyond traditional leadership advice.

You can follow Sir Ashley on LinkedIn at https://www.linkedin.com/in/ashley-bloomfield-knzm-cminstd-b7181b17/

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Do you ever feel the need to be the leader with all the answers?

Do you feel the relentless pressure to bow to the barrage of deliverables that are in front of you every day?

Do you wish you could just get some space?

There’s got to be a better way, right?

This episode is gold if you’re looking for a better way to sustain your own and your people’s performance and growth.

James Miller is an executive coach and host of a rural accommodation business. What’s common to both of these roles is the importance of creating the space for others to breathe out, reflect, and get perspective. James is an absolute master at this.

In this episode, we explore:

1. How, as corporate leader, James dealt with the pressures of having to conform, and how he found freedom and space to be himself during that period
2. Why staying in a job that doesn't serve you can harm your confidence and sense of value.
3. Ways to create the balance between ‘delivery’ and ‘discovery’
4. How to navigate the liminal space, the space between ‘no longer’ and ‘not yet’, and why it’s a critical part of the process of creating what's next.
5. How James has created spaciousness and a sense of unhurriedness in his everyday life, and how that has led to greater creativity, productivity, and fulfillment.
6. The courage needed to make decisions that align with your values and contribute to personal growth and why it’s essential for long-term fulfillment.
7. How hosting others and creating environments that support personal growth can be transformative for both the host and the guests.
8. The power of being present and fully engaged in conversations, creating a space for others to feel heard and valued.
9. Why every day needs to be interesting and different!

You can find James at:

1. Website https://www.idlewildbridgetown.com.au/
2. LinkedIn

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Have you ever wished you could take a career break?

If you’re finding yourself at a career crossroads, or you’re simply seeking more fulfillment and satisfaction from your work, this episode is for you. You’ll see what can be made possible when you get deliberate about creating spaces between the chapters of your career, and learn how to structure ‘time out’ to make the most of your breaks and set a meaningful direction for a well-lived life.

Katie Hair is a career coach, consultant, and facilitator intent on aligning her career with the life she wants to lead. She’s a role model for living a life by design. Her mission is to help others do the same. Together, Katie and I explore:

1. Why taking intentional breaks in your career can lead to personal growth and reinvention.
2. How being deliberate and intentional during breaks can lead to a better understanding of oneself and one's values.
3. The necessity of listening to your inner voice and taking risks to break free from constraints and pursue a desired life path.
4. How the concept of a portfolio career, where individuals have multiple income streams and work on their own terms, is gaining popularity.
5. The need and invitation for organisations to support individuals in pursuing alternative work models and provide autonomy and flexibility.

Check out Katie’s work at https://www.katiehair.co.nz/ and follow her on LinkedIn at https://www.linkedin.com/in/katiehair/

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What happens when you slow down?

If you feel like life is a relentless treadmill, this episode offers an alternative. You’ll get fresh perspectives about what can happen when you unhook from relentless busyness, and an invitation to explore what really matters when it comes to leading yourself and others.

Andrew Maffett is a lifelong adventurer and learner. He recently retired from a successful business life and now lives on his yacht with his wife Donna sailing around South East Asia. From the perspective of someone who has been a driven business leader, Andrew offers his insights and advice around:

1. The cost of busyness in modern society
2. How creating space for stillness and empty times attracts new experiences and insights.
3. What happens when you remove obligations, deadlines, and ‘having somewhere to be next’
4. How honoring our inner pioneering spirit allows us to lead more authentically
5. The power of curiosity to drive learning and growth, and how it has shaped his career and leadership style
6. Why leadership is more than simply driving to achieve goals, and the importance of developing others

You can follow Andrew and Donna on Instagram at @chasing._.horizons

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How effectively can you bring out the best in a group of people?

We can often get trapped into thinking that it’s our role to be the ‘hero’ for a group, where it’s likely that you can be way more effective by being the ‘host’. This episode will help you get out of your own way so you can unlock the potential that exists in those you lead.

Today I’m talking with creative producer and speaker coach D.K. about:

1. Why avoiding the mundane and embracing creativity is essential for effective leadership
2. How the role of a pioneer involves venturing into unexplored territory and creating space for others to follow…
3. …and the role of a host involves facilitating meaningful experiences that fully involves others
4. Why empathy, voice, and participation are essential elements in group settings
5. The power of grace in communication and the significance of quieting one's cleverness
6. The power of simply sitting and being together

You can find D.K. at https://justadandak.com/

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Have you ever found yourself caught in an endless cycle of meetings and tasks, wondering if your leadership is truly making a difference?

What if the most powerful leadership tool isn't your strategic plan or your team's expertise, but your ability to recognise and act on the second chances life gives you?

This episode explores how our personal challenges can become a driving force and focusing tool for positive change and authentic leadership.

Sarah Manley's journey reveals the quiet power of listening to your gut, sitting with uncertainty, and moving beyond the "hero leader" mindset. What emerges is a perspective where leadership becomes less about personal achievement and more about creating space for something greater to emerge—where vulnerability becomes strength and purpose fuels resilience.

Sarah Manley is the Chief Executive of MITEY New Zealand, delivered through the Sir John Kirwan Foundation. MITEY is a purpose-led organisation that provides evidence-based mental health education to primary and intermediate schools in New Zealand.

Born in Chile and adopted by New Zealand and Australian parents at just five weeks old, Sarah's origin story has shaped her deep sense of purpose and commitment to making a difference. In this conversation, she shares:

1. How transforming your relationship with meetings can create space for what truly matters
2. Why journaling for just five minutes a day can shift your focus from what you do to who you want to be
3. How to discern the difference between your gut instinct and your "love filter" when making decisions
4. Why sitting with tension and uncertainty can lead to more authentic leadership choices
5. How personal rock-bottom moments can become catalysts for purpose-driven leadership
6. Why the "pinchy point" of leadership loneliness requires intentional connection with others
7. How to build relationships before you need them rather than waiting for crisis
8. Why recognising that "you cannot not impact" transforms how you show up as a leader

Timestamps

(05:51) Listening to Your Gut

(10:02) Journaling for Clarity

(15:14) The Impact of Personal History

(24:22) Transforming Adversity into Purpose

(27:09) Rising from Rock Bottom

(31:46) Building Support Networks

Resources referenced:

1. The Bigger Me Tool
2. The Network Diagnostic
3. Episode 15: Hazel Maclaurin on the Value of Mentorship

You can find Sarah at https://www.linkedin.com/in/sarah-manley-nz/

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Have you ever wondered what it takes to shift an entire leadership team's mindset and approach in today's fast-changing environment?

This week, I share a case study from a recent 12-month engagement with a senior leadership team. It’s a story about moving from technical perfection to purposeful experimentation, and from control to empowerment.

You'll discover the four essential ingredients that make lasting leadership change possible:

1. How to create the right amount of heat for transformation
2. The support systems that sustain progress
3. Why deliberate experimentation beats perfectionism
4. How connecting change to a bigger purpose keeps momentum alive.

Whether you're leading change in your team or looking to evolve your leadership approach, this real-world example offers practical insights you can apply immediately.

Check out the blog version of this episode at digbyscott.com/thoughts

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What if leadership isn't about having all the answers, but about creating the right space for people to thrive?

And what if the outcomes from meetings weren’t just about being efficiency and effectiveness, but also about being engaging and expansive?

Simon Dowling brings a fascinating blend of legal precision and improvisational creativity to his work with leaders.

We explore how the most impactful leaders intentionally shape the emotional quality of the environments they create – not just to get things done efficiently, but to generate genuine energy and connection.

And we get into the classic tension between the desire for control and the opportunity that exists when you let go.

We explore:

1. The power of "catalyst questions" that spark energy, thinking, and emotional responses
2. The connection between creating space and making intentional choices as a leader
3. The "three E's" framework: balancing Efficiency, Effectiveness, and Emotional quality in leadership
4. The challenge of creating space within busyness rather than seeing it as something separate
5. The concept of "dual awareness" - being conscious of both your internal state and the environment simultaneously
6. The power of combining seemingly contradictory skills: pragmatic legal thinking with improvisational creativity
7. Practical techniques for developing your "noticing muscle" and being more present as a leader

Whether you're leading a team meeting or a major transformation, this conversation will change how you think about the spaces you create and the choices you make within them.

Simon Dowling is a leading thinker on creating and leading collaborative teams and workplaces. As a speaker, facilitator and educator, he is all about equipping leaders with the inspiration and know-how to build strong, highly engaged teams.

Simon began his career as a commercial lawyer, and is also an experienced improviser, including having been a regular cast member on the hit Australian TV show Thank God You’re Here.

He’s the author of ‘Work With Me’, an authoritative work on the power and pragmatics of collaboration, and his writing spreads further with his insightful posts on LinkedIn. He’s a man worth following and a man worth talking with.

Resources referenced:

1. A More Beautiful Question by Warren Berger
2. Develop Dual Awareness
3. The Moment of Choice
4. I Love the Present

You can find Simon at:

Website: https://www.simondowling.com.au/

LinkedIn: https://www.linkedin.com/in/simondowling-aus/

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Are you trapped in a life you didn't consciously choose?

Do you find yourself constantly reacting to demands rather than intentionally responding? Are you seeking a more deliberate way to live and lead that creates impact without burning you out?

In this episode, Derek Sivers shares counterintuitive wisdom about breaking free from unconscious patterns, embracing slow thinking in a reactive world, and designing a life that truly reflects your choices rather than obligations.

We discuss:

1. The power of conscious choice: Derek reveals how recognising the difference between "have to" and "choose to" transformed his relationship with his successful business and ultimately led him to sell it.
2. Slow thinking as a leadership advantage: Learn why pausing before responding leads to more original ideas, better decisions, and more meaningful connections with others.
3. Breaking free from the zeitgeist: Discover how creating distance from mainstream thinking can become your competitive advantage in developing unique perspectives.
4. The simplification technique: Derek explains how clarifying and simplifying complex problems often reveals the solution without needing outside expertise.

About Derek Sivers

Derek is a writer, musician, programmer, and entrepreneur who founded CD Baby (which he sold in 2008 after growing it into the largest seller of independent music online). Now focused on writing and sharing unconventional wisdom, Derek approaches life with deliberate intentionality.

In our conversation, we cover:

1. Why Derek sees moving and changing perspective as essential to growth and learning
2. How to recognise when you're following "useful but not true" assumptions that limit your options
3. The transformative practice of journaling and how it clarifies thinking
4. Why creating a life without an audience to impress can lead to more authentic choices
5. The value of unhurried productivity in a world obsessed with speed
6. How asking better questions often matters more than finding answers

You can find Derek at https://sive.rs/

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

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Have you ever wanted to take a career break? Maybe you’ve taken one and want to get inspiration for the next one? Perhaps you’re curious about how you can make them a part of your organisation’s talent strategy?

Career breaks done well can provide massive benefits for your professional and personal life. This conversation gives you both ideas for the inspiration and implementation of your own career break, as well as ideas for how they can benefit organisations looking to retain and develop their talent.

This episode is a conversation between three colleagues - Katie Hair, Jodi Willocks, Colm Kearney and me. We’ve all recently taken career breaks and gotten a huge amount from them.

We discuss:

(00:09) Introduction to the conversation on career breaks

(06:36) The difference between a "sabbatical" vs. "career break"

(10:36) Recognising when it's time for a change

(15:34) How we frame our time away from work

(20:51) Practical preparations: Financial planning and communication strategies

(29:03) The value of creating space and renewal

(38:18) Why career breaks should be normalised in the future of work

(44:24) The "evaporation" phase: letting everything go to see what remains

(49:18) How breaks accelerate personal growth and leadership development

(54:24) Navigating the emotional journey of a career break

(01:01:11) Practical tools for making the most of your break

(01:07:04) How organisations could better support career breaks

(01:16:02) Final advice for those considering a break

(01:21:36) Conclusion and resources at digbyscott.com/careerbreak

You can learn more about my guests at:

1. Katie Hair: https://www.katiehair.co.nz/ (and check out Episode 5 for a deep dive conversation with Katie)
2. Jodi Willocks: https://www.linkedin.com/in/jodi-willocks-6b035446/
3. Colm Kearney: https://www.linkedin.com/in/colm-kearney/

Sign up to the Career Break community https://digbyscott.com/careerbreak

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

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Have you ever felt caught between competing identities in your professional life? Perhaps you've built a career on expertise and achievement in one domain, only to find yourself navigating an entirely new landscape that fundamentally changes how you're perceived.

Today's conversation explores the importance of evolving your identity as your context changes, and how as we get older, we can get more nuanced in how we relate to the complexity that change brings.

Hazel Maclaurin shares her multifaceted journey as a musician, poet, digital marketing leader, and strategic HR content expert. She discusses the profound impact of mentorship on her career, the importance of storytelling in evoking change, and the necessity of nuance in today's world.

Whether you're wrestling with complexity in your organisation or seeking to honor all dimensions of your life, this conversation offers both wisdom and a refreshingly honest take on what it means to lead with authenticity.

We discuss:

1. The growing importance of ‘adaptive capacity’
2. The power of brilliant mentors
3. The difference between running away from something vs. moving toward something and how that difference transforms our relationship with work and leadership.
4. the value that her ‘squiggly career’ has brought her
5. the importance of embracing nuance in decision-making.
6. the power of storytelling and language in fostering understanding and connection
7. the societal expectations placed on women,
8. the impact of motherhood on professional identity,
9. the significance of self-compassion in personal evolution

Hazel Maclaurin is a strategic HR content expert with over a decade of high-level corporate experience, including roles as global content manager for enterprise at Korn Ferry and global head of content at the Project Management Institute. Her "squiggly career" path—spanning titles including (but not only) musician, poet, digital marketing specialist, and HR strategist—has given her ‘range’ - unique insights and understanding into the human condition and the power of connection through language.

You can find Hazel at:

Website: https://www.hazelmaclaurin.com/

LinkedIn: https://www.linkedin.com/in/hazel-maclaurin-b985a625/

Blog: https://thiswomenswork.com/

Substack: https://thiswomenswork.substack.com

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

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Do you know that feeling when you're in a meeting or delivering a speech and you're caught up in thinking about what you want to say next? Then you completely miss the moment when something happens? And you're scrambling to catch up?

This episode hones in on how we can stay more present to what's going on and then respond in the moment to what's happening so we can engage people more effectively and better navigate messy, complex situations.

You’ll learn:

1. How diving into the unknown fosters creativity and connection
2. Why pre-meeting interactions shape the outcomes of gatherings
3. How language influences our identity and decision-making
4. Why navigating the unknown requires collective effort and presence
5. Four forms of listening that you need to master
6. How nature serves as a powerful teacher for leadership.
7. How systemic change begins with individual awareness and action.
8. Why breath and presence are essential tools for leaders.
9. Why savouring the world leads to deeper understanding and connection.

Adam Cooper is one of those people who sees the world just a little bit differently. Adam grew up in Zimbabwe during a time of profound change, watching a society transform before he moved to New Zealand when he was 18. And that experience of seeing how quickly things can shift has shaped his unique lens on leadership and change.

Adam's known for helping leaders and organisations see possibilities they didn't know existed. And he brings a fascinating blend of strategic thinking and embodied wisdom to his work. He's got this uncanny ability to spot patterns and shifts in society long before they become obvious to everyone else.

Adam designs his own path and is a role model for how you can too.

You can find Adam at:

Website: https://www.creativeleadership.co.nz/

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

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

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How willing are you to let your ideas be destroyed?

That's a scary concept for many people because we can equate good ideas with being worthy.

But what if your worth comes from being a learner and not perfect?

In this messy and complex world where the old structures and systems of society and work are found wanting, we need to evolve and adopt new ideas fast.

If you want to level up how you lead change, innovation, and learning, this episode will teach you:

1. How to create an environment of constructive challenge that enables fresh perspectives and stronger relationships
2. Why Rob believes collaboration trumps competition when problem-solving every time
3. The importance of understanding the purpose behind traditions
4. Why critical thinking should focus on accuracy rather than being right
5. The way information is shared impacts its reception
6. The discipline of patience when planting seeds of wisdom

CO2 Rob Pa’o exemplifies an approach to life and leadership that is about blending curiosity, humility, and integrity into a potent package with plenty of practical wisdom for all of us.

Rob’s heritage is Samoan. He’s a first-generation immigrant to New Zealand and was brought up in the predominantly white city of Christchurch.

Growing up in this environment, as someone who didn’t necessarily look like most other people there, strongly shaped how Rob made sense of who he is.

When Rob and I first met a few years ago, he struck me as someone with a strong sense of who he is, yet with a deep curiosity to keep learning and growing. Rob makes you feel seen, heard, and invited to be bigger. It’s a powerful experience!

You can find Rob on LinkedIn at https://www.linkedin.com/in/co2-robert-pa-o-417b70223/

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

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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/

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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/

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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/

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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/

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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/

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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/

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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-Perception

Other references:

1. Santo, Sam and Ed's Cup Fever
2. Santo Cilauro
3. The Castle
4. Thought Leaders Business School
5. Peter Cook
6. Matt Church
7. Col Fink
8. Tony Wilson
9. Simon Dowling

You 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/

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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:

1. Travel as a catalyst for fresh perspectives
2. Three examples of lasting impact: buildings, design, and service
3. Why reactive mode steals our chance for lasting impact
4. Questions to consider for your own lasting legacy

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

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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 Avoidance

Other references:

1. Brené Brown - “Dare to Lead”
2. Thought Leaders Business School
3. The Rest is Politics Podcast
4. Jennifer Garvey-Berger Episode
5. Adam Cooper Episode

You can find Georgia at:

Website: https://canwetalk.co

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

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

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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:

1. How major burnout at 32 led to life-changing clarity about what truly mattered
2. Why conviction can grow even when confidence feels shaky
3. The questions that form the foundation of authentic commitment to yourself
4. How blind alleys and course corrections actually strengthen your sense of direction
5. Why comparing yourself to others' corporate trajectories misses the point entirely
6. The relationship between authentic living and sustained impact
7. How to honour your values even when the path feels uncertain

Whether 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/

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Do you know that feeling when you're asked a question, you’re under pressure, so you reach for the nearest answer?

Or when you're in a meeting and someone says "let's not overcomplicate this" or "we just need to make a decision" and something inside you knows you're moving too fast, but the momentum carries you forward anyway?

This episode explores what Kate Christiansen calls "the Answer Trap," that invisible current pulling us toward quick closure when what we actually need is better thinking.

Kate shares how our brains, when faced with disruption and complexity, default to comfort-seeking patterns that feel like progress but actually limit our capacity to navigate what's really happening.

What if the biggest risk we face isn't making the wrong decision, but stopping our thinking too soon?

Kate Christiansen is a ‘cognitive detective’ who's spent decades helping leaders think more clearly when it matters most. Having lived through disruptive environments her entire career, she's developed an uncanny ability to see patterns in complexity that others miss.

Kate is the author of "The Answer Trap," a book that names something we've all experienced but never had language for.

In this episode, you'll discover:

1. How to recognise the five "autopilot" thinking patterns that drag us toward premature answers
2. Why disruption makes us crave closure and how this creates a cycle of reactive decision-making
3. How to switch from autopilot to "copilot" by partnering with your brain rather than being controlled by it
4. Why asking "What am I thinking right now?" is the simplest way to break free from default patterns
5. How AI both amplifies the answer trap and offers new ways to enhance our thinking
6. Why the "dodo effect" threatens our cognitive abilities and what we can do about it
7. How to create "surface piercing questions" that move beyond comfortable answers
8. Why slowing down in conversations actually accelerates better outcomes

Timestamps:

(00:00) - The Dodo Effect and Outsourcing Thinking

(10:57) - The Answer Trap: Understanding the Problem

(20:17) - The Relationship with AI: A Double-Edged Sword

(27:39) - Understanding Autopilots in Decision Making

(32:20) - Breaking Free from Autopilot Thinking

(46:09) - The Power of Naming the Answer Trap

Other references:

1. Curly Conversations for Teams Book| Kate Christiansen
2. The Answer Trap | Kate Christiansen
3. The Thrive Cycle | Kate Christiansen
4. Growth Mindset | Carol Dweck
5. Chat GPT

You can find Kate at:

Website: www.katechristiansen.com.au

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

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

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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:

1. Why your first instinct to correct someone's "wrong" viewpoint limits your leadership
2. How to listen for understanding rather than listening to respond
3. The difference between proving your point and improving your viewpoint
4. Why meeting people where they're at is essential for genuine connection
5. How expanding your perspective gives you greater awareness of the complex world we're leading in
6. Practical ways to ask questions that deepen understanding rather than create defensiveness
7. Why curiosity and judgment can't coexist – and which one actually creates influence

Whether 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.

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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

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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.

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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 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

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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

What if the most powerful thing you could do as a leader isn't delivering results or driving change—but simply seeing and hearing the people around you?

Today I'm joined by Jenny Brown. Jenny grew up in apartheid South Africa, classified as a ‘coloured’ person, where she learned what it means to navigate between worlds—not quite belonging fully anywhere, but developing an extraordinary ability to see and be in the spaces between.

She’s got this superpower to read what's really happening in a room - not just what's being said, but what's being felt, what's being avoided, and what needs to be addressed.

She’s also learned to call out what needs to be called out, doing so with a skillfulness that keeps people whole. She understands that leadership isn't about having all the answers - it's about creating space for others to be truly seen and heard.

If you've ever wondered how to create genuine belonging in your organisation, or how your own formative experiences might become your leadership superpower, this conversation will change how you think about what leadership really means.

Timestamps:

(00:00) - The Power of Observation in Leadership

(18:01) - The Journey from Independence to Interdependence

(24:05) - Navigating Difficult Conversations

(27:00) - Calling Out BS with Compassion

(34:18) - Creating Conditions for Belonging

(40:47) - The Broader Impact of Belonging

Other references:

1. The Anxious Generation by Jonathan Haidt
2. Together by Dr Vivek Murthi
3. Belonging by Owen Eastwood
4. Fierce Conversations by Susan Scott
5. A Leader’s Guide to Reflective Practice by Judy Brown
6. Work Human 2023 Study
7. Gallup Employee Engagement Survey
8. What’s Your Bit? by Digby Scott

You can find Jenny at:

LinkedIn: https://www.linkedin.com/in/jenny-b-aa8ba958/

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 life you're living by default could become the life you're crafting by design?

And what if the difference between drifting and deliberately creating your future comes down to one intentional weekend with the person who matters most?

In this solocast, I share what happened when my partner Gillian and I carved out a weekend to create our 'Life by Design' plan. It wasn't about rigid blueprints or perfect forecasts. It was about getting intentional with what we want to create together, and how we might navigate the messiness of making it happen.

You'll discover:

1. Why life by design is the antidote to life by default, and how to shift from one to the other
2. The simple process we used to map out our future without losing space for spontaneity
3. How clustering your ideas into themes makes overwhelming possibilities feel manageable
4. Why reflecting on what's worked (and what hasn't) is crucial before planning what's next
5. How having a shared plan makes everyday decisions easier and less energy-draining
6. Why financial planning isn't just about spreadsheets, but about creating freedom for what matters
7. The tools and templates you can use to start your own life by design journey

Whether you're wrestling with feeling like life is happening to you rather than being shaped by you, curious about how to align your daily choices with your bigger vision, or simply wanting to create something meaningful with your partner, this conversation offers a practical glimpse into what's possible when you get deliberate about designing the life you actually want to live.

If you'd like the tookit and to learn how we use it, go to https://digbyscott.com/lifebydesign

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What if words aren't enough to truly connect with others?

And what if there's an entire dimension of communication we're missing, one that could transform how we lead, how we listen, and how we create trust in our teams?

Today I'm joined by Jordan Harcourt-Hughes, an abstract painter, writer, and communications specialist who's spent fifteen years leading creative teams across the Asia-Pacific. Jordan's journey began with what she calls her "early midlife crisis" at nineteen. A pivotal moment when she realised that traditional language wasn't the complete picture for human connection.

We explore the fascinating concept of vibrational language.How our bodies communicate beyond words, why singing in Monday morning meetings might be more revolutionary than you think, and what happens when we learn to listen not just with our ears, but with our entire being.

Whether you're leading strategy sessions that feel stuck, or simply curious about creating deeper connection in your work, this conversation will change how you think about the spaces between what we say and what we truly communicate.

Timestamps:

(00:00) - Introduction

(01:27) - The Concept of Vibrational Language

(21:06) - Listening Beyond Words

(25:37) - Creating a Trusting Environment

(28:27) - The Importance of Recalibration and Connection

(30:19) - The Challenge of Letting Go

(38:51) - Finding Energy and Inspiration for Change

Other references

1. Down and Out in Paris and London | George Orwell
2. Let Your Life Speak | Parker J. Palmer
3. The Let Go: https://www.digbyscott.com/thoughts/the-let-go
4. Deal in Energy: https://www.digbyscott.com/thoughts/deal-in-energy

You can find Jordan at:

Website:https://jordanharcourthughes.com/

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

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 important measure of your leadership isn't what you achieve while you're in the role, but what continues after you've moved on? It's a question most senior leaders avoid because the answer is often uncomfortable. You've built the strategy, delivered the results, transformed the culture. But if you left tomorrow, how much of it would actually last?

In this special Year in Review episode, Digby reflects on five interconnected themes that emerged from a year of deep conversations with remarkable leaders, change-makers, and systems thinkers. These aren't isolated insights, they're facets of the same question: how do we create change that endures? From understanding complex systems and shifting from hero to host leadership, to embracing unhurried productivity and living with deliberate authenticity, each theme builds toward a powerful framework for leading lasting impact.

This episode is Digby's invitation to step back and see the bigger picture. Drawing on insights from over 50 conversations, personal experiences of burnout and breakthrough, and years of working with leaders across sectors, he maps a journey from crisis-driven leadership through to creating change so embedded that people don't want to go back. You'll discover:

1. How to assess where you sit on the spectrum from crisis-driven to lasting impact leadership (and why most leaders get stuck at stage two)
2. Why systems thinking is essential for addressing root causes rather than just treating symptoms, and how the dragonfly metaphor reframes our understanding of generational impact
3. How shifting from hero to host leadership transforms dependency into capability, and why your job isn't to be the answer but to create conditions where answers emerge
4. Why unhurried productivity isn't about slowing down but about creating spaciousness within the work itself, and how this becomes the foundation for everything else
5. How living deliberately means making daily choices that align with who you truly are, not who you think you should be
6. Why these five themes aren't separate ideas but interconnected pieces that, when working together, create leaders whose impact outlasts their tenure
7. How to measure leadership success differently, focusing on what continues after you're gone rather than what you achieve while you're there

Leading Lasting Impact self-assessment

Other References:

1. James McCulloch Podcast Episode
2. Dr. Richard Hodge Podcast Episode
3. Adam Cooper Podcast Episode
4. Jennifer Garvey Berger Podcast Episode
5. DK Podcast Episode
6. Kate Christiansen Podcast Episode
7. KP (Kirsten Patterson) Podcast Episode
8. Derek Sivers Podcast Episode
9. Antonia Milkop Podcast Episode
10. Simon Dowling Podcast Episode
11. Rachel Paris Podcast Episode
12. Jordan Harcourt Hughes Podcast Episode
13. Cynefin Framework
14. Leading Lasting Impact | Digby Scott
15. Unhurried Productivity Diagnostic

Timestamps:

(00:00) - Introduction & Leading Lasting Impact

(10:25) - Systems Thinking and Complexity

(15:54) - Hero to Host Leadership

(22:39) - Unhurried Productivity

(25:53) - Authenticity & Living Deliberately

(32:28) - Leading Lasting Impact Synthesis

(41:27) - Closing

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/

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

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

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

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

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/

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 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

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/