Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.
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October 21, 20264 min
The Promotion Free Fall
The pressure to prove you deserve a promotion can actually be the very thing holding you back. And here's the kicker: that pressure doesn't always disappear once you get promoted. In this episode, I'm talking about the anxiety and self-doubt that come with promotions and why constantly trying to prove your worth can undermine your confidence. I share an analogy about the uncomfortable feeling of free fall during career transitions and explore how to recognize where insecurity comes from, shift the stories we tell ourselves, and embrace the idea that sometimes, less really is more. Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org
October 14, 20264 min
Should I Stay or Should I Go?
Should I stay or should I go? How long is too long to wait for that next promotion, bigger opportunity, or the recognition I've been working toward? It's a question I'm hearing more and more from my clients, especially as the job market gets tougher and the decision to leave a company isn't so straightforward. In this episode, I'm digging into the growing issue of mid-career stagnation, sharing what I'm seeing with clients who are weighing loyalty against new opportunities, why staying isn't necessarily a bad move, and why leaving isn't always the answer either. Resources Burning Glass Institute - "Sidetracked: The Hidden Crisis in Mid-Career Mobility" Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org
October 7, 20263 min
Own Your Job
Are you really owning your job, or just getting through it? In this episode, I’m thinking about what it actually means to take ownership of your work when you’re not the owner. I’m talking about accountability, curiosity, emotional intelligence, resilience - and how those qualities can help me move through the barriers, complexity, and frustration that come with work. Resources Want to Set Yourself Apart? Own Your Job Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org
September 30, 20261 min
Introducing Season Seven and Winnie Unscripted!
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.
July 1, 20269 min
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 working How complexity, uncertainty, and rapid change are reshaping what leadership requires from us Why avoiding conflict can quietly undermine trust, innovation, and team effectiveness The leadership qualities that become even more valuable as AI continues to evolve Why strategic thinking, judgment, communication, empathy, and influence remain deeply human advantages How growth happens through experimentation, reflection, practice, and challenge The 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
June 24, 202625 min
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 create Why one leader's hidden assumptions were keeping him stuck and preventing real progress How adaptive leadership helps us choose the right approach for the right person and situation What causes leaders to unintentionally overuse their preferred leadership style Why communicating your leadership intent can strengthen trust and improve team performance How trust grows when people move beyond assumptions and gain a deeper understanding of one another The 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
June 23, 202616 min
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 effectiveness The four core components of trust: knowing the person, competence, sincerity, and reliability Why people approach trust completely differently and how misunderstanding that creates friction Practical ways to intentionally strengthen trust through better conversations and clearer expectations Why senior leaders must learn to build trust horizontally across the organization, not just within their teams How understanding someone’s motivations, values, and “currency” improves influence and collaboration The 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
June 10, 202617 min
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 situation How the leadership continuum shifts between directing, collaborating, and delegating The three things I evaluate before deciding how to lead someone How trust, risk tolerance, and leadership instincts shape leadership decisions Why clarity and direction can slowly turn into micromanagement How collaboration and delegation build ownership, growth, and stronger decision-making Why 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
June 3, 202612 min
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 results The three types of stories that influence leadership decisions every day Why certain problems keep repeating until we challenge the assumptions underneath them How stories about other people affect trust, collaboration, and conflict The importance of catching ourselves in the moment and questioning our assumptions Why curiosity is far more productive than self-judgment when trying to grow as a leader How 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
May 27, 202652 min
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 differently Carly’s framework for writing “unignorable” messages that people actually respond to The hidden fears that stop most people from reaching out in the first place Why reaching out is one of the highest leverage things you can do for your career How planting seeds for your future self can create opportunities years later The unexpected internal confidence shift that happens when you consistently put yourself out there Why 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
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