Dig Deeper

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/

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

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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/

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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/

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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/

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

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