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. Anti-Networking: How Relationships Create Opportunity with Carly Valancy

    2d ago

    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

    52 min
  2. The Leadership Power of Tiny Experiments

    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

    13 min
  3. Stop Telling, Start Asking with Winnie da Silva

    May 13

    Stop Telling, Start Asking with Winnie da Silva

    “Leadership at scale isn’t about having all the answers—it’s about drawing out other people’s thinking.” - Winnie da Silva Why do so many leaders feel like they have to carry all the answers, and what is it actually costing them? In this episode, I unpack one of the most overlooked leadership tools: asking better questions. I share why constantly jumping in with solutions can quietly limit your team’s thinking, and how shifting toward thoughtful, open-ended questions can completely change the way you lead. It doesn’t mean stepping back or losing authority, but it does elevate the quality of conversations, decisions, and ownership across your team. You’ll hear me discuss: Why having all the answers can actually hold your team backHow asking questions creates ownership instead of dependencyThe connection between inquiry and reducing defensivenessHow better questions uncover hidden risks, assumptions, and blind spotsWhy leaders who ask more questions tend to make stronger decisionsHow questions build trust and increase accountability across teamsSimple, real-world questions you can use in conversations starting today Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org Example Questions: Understanding someone’s thinking “That’s an interesting point. Tell me more about what you're thinking.”“When you say X, what does that mean to you?”“What would need to be true for this to work?”“What do you care most about in this situation?”Collaboration and partnership “How might we best partner together on this?”“What role would you like me to play here?”“What decision do you need from me today?”Feedback conversations “What feedback do you have for me?”“What’s hard to tell me?”“What are we not talking about that we probably should be?”Vision and goals “If you and your team could only achieve one thing this year, what would it be?”“What challenge, if solved, would make the biggest difference?”“What are your top priorities and why?”Problem-solving and decision-making “What might be the root issue underneath this?”“What are we implicitly saying no to by saying yes?”“What data would change your mind?”

    14 min
  4. Why Your Influence Is Falling Short with Winnie da Silva

    May 6

    Why Your Influence Is Falling Short with Winnie da Silva

    “The issue isn’t the strength of the idea. It’s whether it connects to what the other person cares about.” - Winnie da Silva Why do some ideas land instantly… while others just hang in the air, no matter how well you explain them? In this episode, I break down a simple but powerful leadership concept that can completely change how you influence others, especially when you don’t have formal authority. I share how understanding what people truly care about (their “currency”) can shift conversations, build trust faster, and help your message actually stick. You’ll hear me discuss: Why strong arguments alone don’t guarantee influenceWhat “currency” really means and how it shows up in everyday leadershipHow to spot what someone values based on their behavior and prioritiesSimple ways to reframe your message so it connects and landsHow this applies to stakeholders, feedback, trust-building, and big conversationsWhy influence is less about pushing your point and more about aligning with what matters to others Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    13 min
  5. Why Leadership Development Fails with Winnie da Silva

    Apr 29

    Why Leadership Development Fails with Winnie da Silva

    “The goal isn’t ideas—it’s behavior change that drives business results.” - Winnie da Silva Why do so many leadership programs fall flat even when the content is solid? I’ve seen this play out time and time again over the past two decades. It’s rarely about the quality of the program itself. It’s about what’s happening around it. In this episode, I break down the two factors that actually determine whether leadership development creates real, lasting change. I also share where things tend to go wrong. You’ll hear me discuss: Why leadership development only works when both the leader and the organization are fully engagedThe mindset shifts I consistently see in leaders who grow the fastestWhat it really looks like to apply leadership development in real time (not just learn it)How organizational culture and senior leadership behavior can make or break development effortsWhy treating leadership development as a “check-the-box” exercise leads to poor resultsWhat needs to be in place for leadership growth to actually stick and drive business outcomes Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    7 min
  6. You’re Solving the Wrong Problem with Winnie da Silva

    Apr 22

    You’re Solving the Wrong Problem with Winnie da Silva

    “In leadership, the visible problem is often just the symptom.” - Winnie da Silva Is the problem you’re trying to solve actually the real problem or just the most obvious one? In this episode, I unpack why so many leadership challenges don’t get resolved the way we expect, and how quickly jumping to solutions can keep us stuck in the same cycles. I share a real client story and walk through how to slow down just enough to uncover what’s really driving the issue, so you can create solutions that actually last. You’ll hear me discuss: Why the visible problem is often just a symptom, not the root causeHow pressure and urgency push us into solving the wrong thingThe difference between surface issues and deeper organizational dynamicsA real example of how misalignment at the top created slow decision-makingThe role of trust, expectations, and avoided conversations in team challengesSimple questions I use to dig deeper and challenge my own assumptionsHow pausing, gathering input, and testing solutions leads to better outcomes Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    9 min
  7. Why High Performers Get Coaches with Winnie da Silva

    Apr 15

    Why High Performers Get Coaches with Winnie da Silva

    “Coaching isn’t remediation. It’s acceleration.” - Winnie da Silva Is executive coaching really just a last resort for struggling leaders… or is that completely missing the point? In this episode, I unpack one of the biggest myths around coaching and share what I actually see in my work with high-performing leaders. I explain why leadership coaching is about growth, not fixing, and why the right support at the right time can completely shift your leadership impact. You’ll hear me discuss: Why coaching is often misunderstood as a performance fix instead of a growth acceleratorWhat really changes when a strong leader steps into a bigger, more complex roleHow blind spots show up even for high performers and how I help uncover themWhy reflection is something most leaders don’t get enough of (and why it matters)How coaching creates space to think differently, test ideas, and navigate complexityThe difference between coaching and other tools like feedback, training, or performance managementA real example of how one leader expanded their impact by shifting how they influence and make decisions Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    5 min
  8. My Role. Your Growth. The Results. with Winnie da Silva

    Apr 8

    My Role. Your Growth. The Results. with Winnie da Silva

    “Real leadership work isn’t about fixing people—it’s about addressing root issues.” - Winnie da Silva Are you stepping into bigger leadership… but still thinking and operating the same way? In this episode, I break down what it really takes to grow as a leader when the pressure, complexity, and expectations all level up. I share how I work with leaders and teams, the frameworks behind that work, and why lasting change comes from mindset shifts instead of quick fixes. You’ll hear me discuss: Who I work with and the types of leadership transitions and challenges they faceWhy leadership is less about industry and more about mindset and peopleWhat executive coaching actually looks like and how it drives real resultsWhy leadership development must lead to behavior change, not just learningThe three core areas of my work: coaching, leadership development, and team effectivenessHow to tell if a team is truly effective (and what to look for)Why sustainable results come from addressing root causes, not quick fixes Resources Celebrating 20 Years of Transformative Leadership Episode Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    19 min
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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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