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Dig Deeper

Digby Scott
Dig Deeper
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  • 40. Creating Connection in a Disconnected World, and Space Between the Logs | Jenny Brown
    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's being avoided, and what needs to be addressed.She’s also learned to call out what needs to be called out, doing so with a skillfulness that keeps people whole. She understands that leadership isn't about having all the answers - it's about creating space for others to be truly seen and heard.If you've ever wondered how to create genuine belonging in your organisation, or how your own formative experiences might become your leadership superpower, this conversation will change how you think about what leadership really means.Timestamps:(00:00) - The Power of Observation in Leadership(18:01) - The Journey from Independence to Interdependence(24:05) - Navigating Difficult Conversations(27:00) - Calling Out BS with Compassion(34:18) - Creating Conditions for Belonging(40:47) - The Broader Impact of BelongingOther references:The Anxious Generation by Jonathan HaidtTogether by Dr Vivek MurthiBelonging by Owen EastwoodFierce Conversations by Susan Scott
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  • 39. How to Create Your Life By Design
    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.You'll discover:Why life by design is the antidote to life by default, and how to shift from one to the otherThe simple process we used to map out our future without losing space for spontaneityHow clustering your ideas into themes makes overwhelming possibilities feel manageableWhy reflecting on what's worked (and what hasn't) is crucial before planning what's nextHow having a shared plan makes everyday decisions easier and less energy-drainingWhy financial planning isn't just about spreadsheets, but about creating freedom for what mattersThe tools and templates you can use to start your own life by design journeyWhether you're wrestling with feeling like life is happening to you rather than being shaped by you, curious about how to align your daily choices with your bigger vision, or simply wanting to create something meaningful with your partner, this conversation offers a practical glimpse into what's possible when you get deliberate about designing the life you actually want to live.If you'd like the tookit and to learn how we use it, go to https://digbyscott.com/lifebydesignCheck 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/
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  • 38. Questioning Everything, Living Intentionally, and Why Singing in Meetings Changes Everything | Jordan Harcourt-Hughes
    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 the fascinating concept of vibrational language.How our bodies communicate beyond words, why singing in Monday morning meetings might be more revolutionary than you think, and what happens when we learn to listen not just with our ears, but with our entire being.Whether you're leading strategy sessions that feel stuck, or simply curious about creating deeper connection in your work, this conversation will change how you think about the spaces between what we say and what we truly communicate.Timestamps:(00:00) - Introduction(01:27) - The Concept of Vibrational Language(21:06) - Listening Beyond Words(25:37) - Creating a Trusting Environment(28:27) - The Importance of Recalibration and Connection(30:19) - The Challenge of Letting Go(38:51) - Finding Energy and Inspiration for ChangeOther referencesDown and Out in Paris and London | George OrwellLet Your Life Speak | Parker J. PalmerThe Let Go: https://www.digbyscott.com/thoughts/the-let-goDeal in Energy: https://www.digbyscott.com/thoughts/deal-in-energyYou can find Jordan at:Website:https://jordanharcourthughes.com/LinkedIn: https://www.linkedin.com/in/jordanharcourthughes/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/
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  • 37. When Leadership Feels Like Swimming Upstream
    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 to us even in the most challenging situations.You'll discover the difference between external structural forces (like organisational culture and economic pressures) and the internal ones we carry within us (our assumptions, beliefs, and the stories we tell ourselves). Most crucially, you'll learn how shifting from being subject to change to becoming an agent of change can transform both your leadership and your wellbeing.Whether you're a CEO feeling the weight of responsibility or anyone navigating complexity and burnout, this episode offers a fresh perspective on finding your way to the riverbank when the current feels too strong.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/
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  • 36. Stepping Into Visibility, Reading the Room, and Why Leadership Isn't About Being Perfect | Cam Fink
    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 the skills that make you compelling on video are the same ones that make you an engaging leader.Whether you're leading a team meeting or recording your first LinkedIn video, this conversation will change how you think about showing up authentically in any situation where you need to influence and inspire others.Cam Fink is a videographer, director, and the creator of the brilliantly named course "Be Less Shit on Camera." He's also my go-to person for helping me feel comfortable and confident whenever there's a camera pointed in my direction.Timestamps:(00:00) - The Need for Human Connection(06:02) - The Role of Energy in Leadership(17:47) - Visibility and Connection in Leadership(24:51) - Shifting from Bystander to Activator(32:11) - Embracing Authenticity and Vulnerability(36:12) - Navigating Negative Feedback and Self-PerceptionOther references:Santo, Sam and Ed's Cup FeverSanto CilauroThe CastleThought Leaders Business SchoolPeter CookMatt ChurchCol FinkTony WilsonSimon DowlingYou can find Cam Fink at:Website: https://www.camfink.com/LinkedIn: https://www.linkedin.com/in/camfink/Course:
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About Dig Deeper

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/
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