Transformative Leadership Conversations with Winnie da Silva

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 - [email protected]

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.

“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 - [email protected]

"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 - [email protected]

“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 - [email protected]

“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 - [email protected]

“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 - [email protected]

“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 - [email protected]

“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 behaviors
• How tiny experiments reduce overwhelm and make meaningful change feel more achievable
• Why confidence is usually built through action and repetition, not before it
• The power of small, consistent leadership behaviors over dramatic transformation
• How reflection frameworks like “plus, minus, next” help create sustainable growth
• What I learned from running my own public leadership experiment around strategic thinking
• Why experimentation, adaptability, and continuous learning are becoming essential leadership skills today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

Tiny Experiments in Leadership Thinking episode - December 2025

“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 back
• How asking questions creates ownership instead of dependency
• The connection between inquiry and reducing defensiveness
• How better questions uncover hidden risks, assumptions, and blind spots
• Why leaders who ask more questions tend to make stronger decisions
• How questions build trust and increase accountability across teams
• Simple, real-world questions you can use in conversations starting today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

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?”