Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva
  • 4.7 (20)
  • Management
  • Updated Weekly

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

  1. 6d ago

    Introducing Season 7 of Transformative Leadership Conversations

    Welcome to Season Seven! Do you like tiny experiments? That's what's happening this season on Transformative Leadership Conversations. Winnie da Silva is going to be sharing short weekly episodes called Winnie Unscripted tackling all things leadership, from what's in the news, to new insights and ideas from client work to questions for experts and leaders in the community. There will also be a monthly full-length interview with a leading expert sharing their thoughts and experiences. Want to get involved? Reach out to Winnie da Silva with your questions, challenges, insights and ideas.

  2. Jul 1

    You Are Built for Transformation with Winnie da Silva

    “The moments that stretch us most as leaders often become the moments that transform us most — if we are willing to engage them intentionally.” - Winne da Silva Growth sounds inspiring until it asks you to let go of the habits, mindsets, and approaches that got you where you are today. So what happens when your greatest strengths start becoming your biggest limitations? And how do you continue evolving as a leader in a world that's changing faster than ever before? In this final episode of Season 6, I'm reflecting on the biggest lessons from our Think Differently, Transform How You Lead series. I revisit the leadership myths we've challenged, the frameworks we've explored, and the reality that meaningful transformation is rarely quick, easy, or comfortable. You'll hear me discuss: Why transformation often begins when the approaches that once made us successful stop workingHow complexity, uncertainty, and rapid change are reshaping what leadership requires from usWhy avoiding conflict can quietly undermine trust, innovation, and team effectivenessThe leadership qualities that become even more valuable as AI continues to evolveWhy strategic thinking, judgment, communication, empathy, and influence remain deeply human advantagesHow growth happens through experimentation, reflection, practice, and challengeThe role trusted partners, coaches, and advisors can play in accelerating transformation Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    You Are Built for Transformation with Winnie da Silva

  3. Jun 24

    Beyond the Framework: Three Real Stories of Leadership Transformation with Winnie da Silva

    "Transformation of any kind is rarely one insight, one coaching session, one workshop, or one conversation.” - Winnie da Silva Leadership challenges are rarely just about what’s happening on the surface. The issue that keeps resurfacing, the team dynamic that won’t improve, or the frustration you can’t seem to solve may actually be driven by something much deeper. In this episode, I share three real client stories from my executive coaching, leadership development, and team effectiveness work to show how lasting transformation happens when we uncover the stories, assumptions, leadership habits, and trust dynamics shaping our behavior and results. You'll hear me discuss: How the stories we tell ourselves influence the way we lead and the results we createWhy one leader's hidden assumptions were keeping him stuck and preventing real progressHow adaptive leadership helps us choose the right approach for the right person and situationWhat causes leaders to unintentionally overuse their preferred leadership styleWhy communicating your leadership intent can strengthen trust and improve team performanceHow trust grows when people move beyond assumptions and gain a deeper understanding of one anotherThe common thread connecting leadership challenges across individuals, teams, and organizations Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    Beyond the Framework: Three Real Stories of Leadership Transformation with Winnie da Silva

  4. Jun 23

    Building Trust Intentionally with Winnie da Silva

    “Trust doesn’t just magically happen or appear. It’s built through deliberate action and honest conversations.” - Winnie da Silva Trust impacts everything at work - communication, collaboration, influence, decision-making, and team culture. But most leaders still treat it like something that naturally develops over time instead of something that needs real intention and strategy. In this episode, I’m unpacking how trust actually gets built, why it breaks down so easily, and the practical frameworks I use with leadership teams to strengthen the relationships that matter most. You’ll hear me discuss: Why broken trust quietly drains energy, productivity, and team effectivenessThe four core components of trust: knowing the person, competence, sincerity, and reliabilityWhy people approach trust completely differently and how misunderstanding that creates frictionPractical ways to intentionally strengthen trust through better conversations and clearer expectationsWhy senior leaders must learn to build trust horizontally across the organization, not just within their teamsHow understanding someone’s motivations, values, and “currency” improves influence and collaborationThe stakeholder analysis tool I use to help leaders build stronger, more strategic work relationships Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    Building Trust Intentionally with Winnie da Silva

  5. Jun 10

    Intentional Leadership Is Adaptive Leadership with Winnie da Silva

    “Adaptive leadership is about choosing the right leadership approach for the right people in the right situation.” - Winnie da Silva Some leaders hold on too tightly. Others delegate too fast. In this episode, I break down the adaptive leadership framework I’ve used for years with everyone from first-time managers to CEOs, and explain why effective leadership is rarely about sticking to one style. I walk through the continuum of directing, collaborating, and delegating, and share how I decide which approach fits the person, the situation, and the moment. You’ll hear me discuss: Why adaptive leadership is about choosing the right leadership approach for the right person and situationHow the leadership continuum shifts between directing, collaborating, and delegatingThe three things I evaluate before deciding how to lead someoneHow trust, risk tolerance, and leadership instincts shape leadership decisionsWhy clarity and direction can slowly turn into micromanagementHow collaboration and delegation build ownership, growth, and stronger decision-makingWhy great leaders constantly reassess and adapt instead of relying on one leadership style Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    Intentional Leadership Is Adaptive Leadership with Winnie da Silva

  6. Jun 3

    Rethinking Your Stories with Winnie da Silva

    “If we want better results, we have to examine the stories and assumptions driving our behavior.” - Winnie da Silva Some leadership challenges don’t start with strategy or communication, but rather they start with the stories we’re telling ourselves. The assumptions running quietly in the background about who I am, who other people are, and how things work. In this episode, I explore how those internal narratives shape our behavior, influence our leadership, and ultimately impact the results we get. I also break down how changing the story can lead to completely different outcomes. You’ll hear me discuss: How the stories we tell ourselves shape our behavior and resultsThe three types of stories that influence leadership decisions every dayWhy certain problems keep repeating until we challenge the assumptions underneath themHow stories about other people affect trust, collaboration, and conflictThe importance of catching ourselves in the moment and questioning our assumptionsWhy curiosity is far more productive than self-judgment when trying to grow as a leaderHow adopting a new story can create better behaviors and better outcomes Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    Rethinking Your Stories with Winnie da Silva

  7. May 27

    Anti-Networking: How Relationships Create Opportunity with Carly Valancy

    “When you can show up in service of someone else’s work ahead of your own, it stops feeling transactional.” - Carly Valancy Networking has become one of the most dreaded words in professional life. It feels transactional, awkward, and exhausting. But in a world increasingly driven by AI and digital communication, real human connection may be more valuable than ever. In this episode, I sit down with Carly Valancy, founder of Reach Out Party, to talk about her philosophy of “anti-networking” - a more human, generous, and courageous way to build relationships and create opportunity. You’ll hear us discuss: Why traditional networking feels so uncomfortable and how to approach it differentlyCarly’s framework for writing “unignorable” messages that people actually respond toThe hidden fears that stop most people from reaching out in the first placeWhy reaching out is one of the highest leverage things you can do for your careerHow planting seeds for your future self can create opportunities years laterThe unexpected internal confidence shift that happens when you consistently put yourself out thereWhy meaningful human connection is becoming a major differentiator in an AI-driven world Resources Carly Valancy on Website | Reach Out Party | Tether | Substack | LinkedIn | Momentum Growth Plan Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    Anti-Networking: How Relationships Create Opportunity with Carly Valancy

  8. May 20

    The Leadership Power of Tiny Experiments

    “Leadership growth happens when we begin practicing new behaviors in the real world.” - Winnie da Silva Some of the biggest leadership breakthroughs don’t come from massive reinventions. They come from one small shift repeated consistently over time. In this episode, I’m digging into why so many leaders get stuck thinking about growth instead of actually practicing it and why tiny experiments might be one of the most powerful tools for real leadership development. You’ll hear me discuss: Why leaders often get trapped thinking about growth instead of practicing new behaviorsHow tiny experiments reduce overwhelm and make meaningful change feel more achievableWhy confidence is usually built through action and repetition, not before itThe power of small, consistent leadership behaviors over dramatic transformationHow reflection frameworks like “plus, minus, next” help create sustainable growthWhat I learned from running my own public leadership experiment around strategic thinkingWhy experimentation, adaptability, and continuous learning are becoming essential leadership skills today Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org Tiny Experiments in Leadership Thinking episode - December 2025

    The Leadership Power of Tiny Experiments
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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

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