

Dig Deeper
Digby Scott
There's no one way to lead. Yet we need to find a way. Our own way. And it can be hard to get right. As we find our way to lead it can be useful to listen to how others found theirs.
Each fortnight, I’ll share a rich, unhurried conversation with someone who’s leaned into and learned from the challenges of leadership, change, and life while staying true to themselves.
You'll get to experience me doing what I do best: asking the surface-piercing questions to help people see what they couldn't see before. Including you.
Learn more about my courses and get more resources at https://www.digbyscott.com/
And follow me on LinkedIn here: https://www.linkedin.com/in/digbyscott/
Each fortnight, I’ll share a rich, unhurried conversation with someone who’s leaned into and learned from the challenges of leadership, change, and life while staying true to themselves.
You'll get to experience me doing what I do best: asking the surface-piercing questions to help people see what they couldn't see before. Including you.
Learn more about my courses and get more resources at https://www.digbyscott.com/
And follow me on LinkedIn here: https://www.linkedin.com/in/digbyscott/
Episodes
Mentioned books

May 26, 2025 • 7min
21. When Stepping Away Creates More Impact Than Stepping In
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:How to recognise when your heroic tendencies are holding your team backThe difference between stepping away and stepping out – and why timing mattersPractical strategies for creating psychological safety that allows others to step upHow to build sustainable systems that don't depend on your constant interventionWhy focusing on who you build is more important than what you buildSpecific tools and approaches to make the hero-to-host transition successfullyHow to celebrate team successes in ways that reinforce collaborative cultureThe art of identifying opportunities to step back without losing momentumWhether 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/planonapageCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

May 19, 2025 • 55min
20. Embracing Vulnerability, Navigating Rock Bottom, and Leading with Purpose | Sarah Manley
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:How transforming your relationship with meetings can create space for what truly mattersWhy journaling for just five minutes a day can shift your focus from what you do to who you want to beHow to discern the difference between your gut instinct and your "love filter" when making decisionsWhy sitting with tension and uncertainty can lead to more authentic leadership choicesHow personal rock-bottom moments can become catalysts for purpose-driven leadershipWhy the "pinchy point" of leadership loneliness requires intentional connection with othersHow to build relationships before you need them rather than waiting for crisisWhy recognising that "you cannot not impact" transforms how you show up as a leaderTimestamps(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 NetworksResources referenced:The Bigger Me ToolThe Network DiagnosticEpisode 15: Hazel Maclaurin on the Value of MentorshipYou can find Sarah at https://www.linkedin.com/in/sarah-manley-nz/Check out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

May 12, 2025 • 11min
19. How Leadership Teams Evolve
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: How to create the right amount of heat for transformationThe support systems that sustain progressWhy deliberate experimentation beats perfectionismHow 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/thoughtsCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

May 5, 2025 • 1h 4min
18. Why Creating Space Matters More Than Efficiency | Simon Dowling on Intentional Leadership
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:The power of "catalyst questions" that spark energy, thinking, and emotional responsesThe connection between creating space and making intentional choices as a leaderThe "three E's" framework: balancing Efficiency, Effectiveness, and Emotional quality in leadershipThe challenge of creating space within busyness rather than seeing it as something separateThe concept of "dual awareness" - being conscious of both your internal state and the environment simultaneouslyThe power of combining seemingly contradictory skills: pragmatic legal thinking with improvisational creativityPractical techniques for developing your "noticing muscle" and being more present as a leaderWhether 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:A More Beautiful Question by Warren BergerDevelop Dual AwarenessThe Moment of ChoiceI Love the PresentYou can find Simon at:Website: https://www.simondowling.com.au/LinkedIn: https://www.linkedin.com/in/simondowling-aus/Check out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

8 snips
Apr 21, 2025 • 56min
17. Choosing Not Reacting, The Power of Slow Thinking, and Life Beyond the Zeitgeist | Derek Sivers
Derek Sivers, a writer and entrepreneur known for founding CD Baby, shares his unconventional wisdom on living intentionally. He discusses the power of conscious choice and how identifying what we 'choose to' do, as opposed to what we 'have to' do, can change our lives. Sivers emphasizes the advantages of slow thinking, leading to better decisions and originality. He also explores the importance of questioning societal norms and how simplifying complex problems can yield unexpected solutions, pushing listeners towards deeper self-reflection.

Apr 7, 2025 • 1h 23min
16. How to Take A Career Break and Return Stronger: An In-Depth Guide
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/careerbreakYou can learn more about my guests at: Katie Hair: https://www.katiehair.co.nz/ (and check out Episode 5 for a deep dive conversation with Katie)Jodi Willocks: https://www.linkedin.com/in/jodi-willocks-6b035446/Colm Kearney: https://www.linkedin.com/in/colm-kearney/Sign up to the Career Break community https://digbyscott.com/careerbreakCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

Mar 24, 2025 • 59min
15. The Value of Mentorship, Embracing Nuance, and Finding Your Red Thread | Hazel Maclaurin
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:The growing importance of ‘adaptive capacity’The power of brilliant mentorsThe difference between running away from something vs. moving toward something and how that difference transforms our relationship with work and leadership.the value that her ‘squiggly career’ has brought her the importance of embracing nuance in decision-making. the power of storytelling and language in fostering understanding and connectionthe societal expectations placed on women, the impact of motherhood on professional identity, the significance of self-compassion in personal evolutionHazel 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.comCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/#subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

Mar 10, 2025 • 1h
14. Natural Systems, Nervous Systems, and Navigating Change | Adam Cooper
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:How diving into the unknown fosters creativity and connectionWhy pre-meeting interactions shape the outcomes of gatheringsHow language influences our identity and decision-makingWhy navigating the unknown requires collective effort and presenceFour forms of listening that you need to masterHow nature serves as a powerful teacher for leadership.How systemic change begins with individual awareness and action.Why breath and presence are essential tools for leaders.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/Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

Feb 24, 2025 • 55min
13. Breaking Out of Boxes, Constructive Challenge, and the Gift of Heritage | CO2 Rob Pa'o
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: How to create an environment of constructive challenge that enables fresh perspectives and stronger relationshipsWhy Rob believes collaboration trumps competition when problem-solving every timeThe importance of understanding the purpose behind traditionsWhy critical thinking should focus on accuracy rather than being rightThe way information is shared impacts its receptionThe discipline of patience when planting seeds of wisdomCO2 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/Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribe Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/

Feb 10, 2025 • 1h 1min
12. Systems Thinking, The Power of Imagination, and Generational Wisdom | Dr. Richard Hodge
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: Why understanding value is crucial for effective leadership and decision-makingHow relevance is determined by how well we align our actions with our valuesHow the long tail of consequences highlights the impact of our actions over timeWhy community engagement is essential for sustainable changeThe importance of efficiency not overshadowing ethics in organisational practicesHow generational wisdom plays a crucial role in systems thinkingWhy imagination is essential for envisioning changeHow making small, incremental steps can lead to significant transformationHow defining 'enough' is vital for personal equilibrium.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 ChoicesYou 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-gameCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/