Dig Deeper

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. Jo...

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,...

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...

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 fres...

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 c...

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 a...

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," t...

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....

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 b...

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 build...

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 abo...

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 buil...

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 Zeal...

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...

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 De...

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'l...

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...

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 her...

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 to...

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 ma...

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 impactfu...

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,...

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 care...

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...

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 a...