Dig Deeper

• 24. The Man Behind the Microphone, Unhurried Productivity, and the Power of ‘I-Matter’ Conversations | Digby Scott

  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 mic.We get into:Why "meeting people where they're at" transforms resistance into meaningful connectionHow burnout at 30 led to a complete reevaluation of my approach to life and workThe distinction between being "nice" versus being "kind" in leadershipWhy connection before content is the foundation of trust in any relationshipHow unhurried productivity is a state of mind, not just a state of movementWhy pivotal moments with "tough love" mentors can shape our leadership journeyHow embracing discomfort and messiness might be the gateway to our most significant growthWhether you're wrestling with busyness, curious about building trust quickly with new teams, or simply interested in the philosophy behind Dig Deeper, this conversation offers a glimpse behind the curtain that might change how you think about creating space for what truly matters.In this role-reversal episode, Antonia skillfully draws out perspectives on my journey from being a people pleaser to someone who stands for something, and why focusing on intentionality rather than constant activity leads to more meaningful outcomes.Timestamps:(00:00) - Introduction(05:16) - The Importance of Intentionality (12:09) - Pivotal People and Moments in Life(15:32) - Building Trust in Leadership(23:40) - The Power of Connection Before Content(36:27) - Unhurried Productivity: Finding Balance in Busy Lives (41:02) - Embracing Discomfort and Uncertainty in LeadershipYou can find Antonia at:LinkedIn: https://www.linkedin.com/in/antoniamilkop/Others mentioned:Cam Fink: https://www.camfink.com/Simon Dowling: https://dig-deeper.captivate.fm/episode/18-why-creating-space-matters-more-than-efficiency-simon-dowling-on-intentional-leadershipGeorgia Murch: https://georgiamurch.com/Jennifer Garvey Berger: https://www.cultivatingleadership.com/team-member/jennifer-garvey-bergerAdam Cooper: https://dig-deeper.captivate.fm/episode/14-natural-systems-nervous-systems-and-navigating-change-adam-cooperCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/subscribeFollow me on LinkedIn

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• 23. How to Bring Both Your Head and Heart to Leadership

  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 episode, I share my experience of emotional disconnection during a recent transition and how it affected my leadership. I explore the stark differences between head-only and heart-centred leadership approaches, and I share some practical steps to integrate emotional awareness into your leadership practice without sacrificing results.You'll learn:Why numbness in one area of life inevitably affects your leadership effectivenessHow to recognise when you're operating purely from the head versus connecting with heartThe difference between task-focused and emotionally intelligent leadership responsesPractical ways to schedule "heart time" and celebrate wins that create deeper team connectionHow vulnerability and courage become essential tools for authentic leadershipWhy connection becomes even more crucial during tight deadlines and high-pressure periodsCheck out my services and offerings https://www.digbyscott.com/Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribeFollow me on LinkedIn https://www.linkedin.com/in/digbyscott/

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• 22. Embracing Confusion, The Power of Idealism, and Cultivating a Well-Lived Life | Jennifer Garvey-Berger

  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 often happens precisely when we're willing to step into discomfort rather than rushing to make it disappear.Jennifer Garvey-Berger is a thoughtful disruptor who's constantly questioning how we might do business, relationships, family, and leadership better. As CEO of Cultivating Leadership, she's spent decades helping leaders navigate complexity and uncertainty. Jennifer brings a fascinating blend of intellectual rigor and lived experience to our conversation, including her bold experiment of buying a house with twelve friends in France to deliberately create a different way of living. In this episode, you'll discover:How confusion serves as a necessary gateway to learning and growthWhy certainty, despite feeling comfortable, often blocks our ability to discover new possibilitiesHow good conversations create something neither person had thought of beforeWhy crafting a meaningful life requires questioning default assumptionsHow deliberate disruption can lead to more authentic ways of working and livingWhy play and exploration remain essential elements of leadership at any ageHow creating intentional communities can challenge our assumptions about work/life separationWhy our idealism is not something to outgrow but rather a strength to cultivateTimestamps(00:00) The Value of Confusion(08:47) The Quest for a Better World(14:55) Living Fully vs. To-Do Lists(32:18) Creating a Unique Living Environment(40:03) Growth Through Difficulties(42:28) Giving Less FucksOther references:David Whyte: https://www.goodreads.com/quotes/9100423-what-you-can-plan-is-too-small-for-you-toRichard Bach: https://en.wikipedia.org/wiki/Illusions_(Bach_novel)Oliver Burkeman: https://en.wikipedia.org/wiki/Four_Thousand_Weeks:_Time_Management_for_MortalsVito Perrone: https://www.gse.harvard.edu/ideas/news/11/09/hgse-remembers-vito-perroneThomas Huebl: https://thomashuebl.com/Heidi Brookes: https://www.cultivatingleadership.com/team-member/heidi-brooksAndrew Maffett: https://player.captivate.fm/episode/8dc40ef3-104d-4a48-a38e-495ed4650abbAdam Cooper: https://player.captivate.fm/episode/48bf4ecf-f533-47d3-943e-2445135d473dYou can find Jennifer...

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• 21. When Stepping Away Creates More Impact Than Stepping In

  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 growth.I'll share practical insights on how stepping away strategically can enhance your leadership effectiveness, create self-sustaining systems, and build the kind of collaborative culture where everyone thrives. This isn't about becoming passive or disengaged. It's about becoming the kind of leader who creates ecosystems rather than dependencies.You'll learn:How to recognise when your heroic tendencies are holding your team backThe difference between stepping away and stepping out – and why timing mattersPractical strategies for creating psychological safety that allows others to step upHow to build sustainable systems that don't depend on your constant interventionWhy focusing on who you build is more important than what you buildSpecific tools and approaches to make the hero-to-host transition successfullyHow to celebrate team successes in ways that reinforce collaborative cultureThe art of identifying opportunities to step back without losing momentumWhether you're burning out from trying to be everything to everyone, or you're ready to create lasting impact beyond your direct involvement, this episode will reshape how you think about what leadership really means.Download the Plan on a Page mentioned in this episode here: https://www.digbyscott.com/planonapageCheck 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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• 20. Embracing Vulnerability, Navigating Rock Bottom, and Leading with Purpose | Sarah Manley

  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:How transforming your relationship with meetings can create space for what truly mattersWhy journaling for just five minutes a day can shift your focus from what you do to who you want to beHow to discern the difference between your gut instinct and your "love filter" when making decisionsWhy sitting with tension and uncertainty can lead to more authentic leadership choicesHow personal rock-bottom moments can become catalysts for purpose-driven leadershipWhy the "pinchy point" of leadership loneliness requires intentional connection with othersHow to build relationships before you need them rather than waiting for crisisWhy recognising that "you cannot not impact" transforms how you show up as a leaderTimestamps(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 NetworksResources referenced:The Bigger Me ToolThe Network DiagnosticEpisode 15: Hazel Maclaurin on the Value of MentorshipYou can find Sarah at https://www.linkedin.com/in/sarah-manley-nz/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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