Dig Deeper

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 ep...

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, th...

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...

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...

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 c...

What if the very language you use—from "my target" to "our target," from "my client" to "our client"—is either building or breaking the culture you're trying to create? And what if being constantly busy is actually preventing the very work that matters most? In this conversation, I'm catching up with my mate Colin Ellis in a traditional English pub in Winchester. Colin's a five-time best-selling a...

What if the gap between being curious and creating real change is just one small action? And what if the leadership move you've relied on your whole career is actually limiting your impact? This short episode cuts through the noise to explore three powerful distinctions that can transform how you lead. These aren't abstract theories. They're practical frameworks that help you navigate the messy, c...

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...

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 aski...

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 r...

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, r...

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...

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 bluep...

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...