Dig Deeper

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 de...

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...

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...

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...

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.<...

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...

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...

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 th...

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 w...

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 w...

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...

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...

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...

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.

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...

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 F...

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 bef...

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...

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...

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...

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 ep...

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 ofte...

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...

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 le...

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: 

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 int...

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:

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 collea...

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 i...

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 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: 

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 busines...

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...

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 co...

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:

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/bl...

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 think...

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 ex...

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...

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 sh...

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 of...

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: 

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:

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...

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, an...