Transformative Leadership Conversations with Winnie da Silva

“Immigrant entrepreneurs navigate challenges, build thriving businesses, and show us what leadership can look like when resilience and reinvention go hand in hand.”

What if the real secret to America's success isn't who was born here, but who chose to come here? In this episode of Transformative Leadership Conversations, I discuss the powerful and often overlooked role immigrant entrepreneurs play in shaping not just our economy but...

“Leadership isn’t about being perfect or popular. It’s about making decisions, taking responsibility, and developing the skills that allow us to show up with courage and confidence.” - Lorraine Connell

Are we unknowingly holding kids back by tying leadership to titles, popularity, and perfection? Could our entire approach to teaching leadership be setting young people up to fail before they even begin?

In this episode, I sit down wit...

"All leaders should be leading with kindness and empathy and respect for other people, which in general, I think means by leading with example." - Aradhna da Silva



Could the clearest vision for future leadership come not from boardrooms, but from high school classrooms?

In this episode, I flip the mic and turn to the next generation. After speaking at my daughter’s high school career day, I invited students to share their raw, unfil...

“If we’re serious about developing the next generation of leaders, we have to be just as serious about questioning the models we’re handing down.”- Winnie da Silva

Is Gen Z quietly rewriting the rules of leadership - and are we even paying attention? Seventy-two percent (72%) of Gen Z would prefer a non-managerial path to career advancement. They see leadership roles as too high stress and low reward. In this episode of Transformati...

"I think we overestimate the importance of knowing and underestimate the power of listening." - James Misner

What if the biggest thing holding back real change is the way we try to create it? In this conversation of Transformative Leadership Conversations, I speak with James Misner — a leader, storyteller, and deep thinker who challenges how we show up for others, especially those on the margins. His perspective is both disarming an...

‘’Even in a non-profit context, issues of sharing power and mutual respect and dignity are essential and not universal.” - Rebecca Vander Meulen

What does it take to lead with courage, clarity, and compassion when the systems around you collapse—almost overnight? In this episode of Transformative Leadership Conversations, I speak with Rebecca Vander Meulen, Executive Director of the J.C. Flowers Foundation. Rebecca has spent over tw...

"The need for leaders who fund, champion, and drive social causes has only intensified — we need them now more than ever." - Winnie da Silva

What if the most powerful leadership lessons aren’t coming from boardrooms—but from leaders fighting for dignity, justice, and community impact? In this episode of Transformative Leadership Conversations, I explore stepping beyond the walls of traditional leadership and into the world where ret...

"You combine the gender wage gap with the work breaks, what you get is a retirement account that has less money in it at the point of retirement. And then we outlive men.” - Jean Chatzky

What if the way you feel about money is more powerful than what you actually know about it? Managing money is not about being perfect — but just about building the right habits, over and over again. In this episode of Transformative Leadership Conve...

"You cannot negotiate against yourself. Ask questions, gather data, be prepared—but don’t assume the answer before you even start the conversation." - Gini Dietrich

What if the thing holding you back from making more money… is you? In this episode of Transformative Leadership Conversations, I’m chatting with Gini Dietrich, a seasoned PR pro and the founder of Spinsucks. Gini’s not just a business owner, she’s someone who’s learned t...

What if the reason you're not earning what you're worth has nothing to do with your skills — and everything to do with the stories you believe about money? Are you showing up like someone who knows their value… or playing it small to keep the peace? Let’s be real — money is messy. It brings up all kinds of emotions, expectations, and unspoken rules. In this solo episode, I’m sharing something personal: my own journey around money, ...

“No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal

Is your pitch holding you back more than your business idea? Are you making it easy for investors to dream the dream with you? In this episode, I sit down with Medha Agarwal, General Partner at Defy, to talk about the unique challenges founders face—especially women—when pitching their startups, securing funding, and leading throu...

"My role is catching the ideas and making them happen." – Stephanie Unwin

Is your leadership moving forward, or are you just keeping busy?

In the fast-paced world of executive leadership and entrepreneurship, it can feel impossible to carve out time to think strategically. But what if making space for reflection isn’t a luxury—it’s the key to unlocking long-term success? In this episode of Transformative Leadership Conversations, I s...

What makes some founders incredible leaders—and others impossible to work with? They are visionaries, but are they always great leaders? Founders bring passion, vision, and drive, but they can also be intense, stubborn, and relentless. Working with them isn’t just about executing their vision—it’s about knowing when to support, when to challenge, and how to scale alongside them. So how do you do that effectively?

In this episode of ...

“Leadership without courage isn't leadership at all, but courage without integrity is dangerous.’’ - Winnie da Silva

What if your fear was the key to unlocking your greatest leadership potential? In this episode of Transformative Leadership Conversations, I explore the often-overlooked power of fear in leadership. Fear is something all leaders face, but it's not the fear itself that defines us—it's how we respond to it. You’ll hear ...

"The old model of leadership, commanding, dominating, and never admitting failure, is outdated, and more importantly, it's ultimately ineffective." - Winnie da Silva

Is humility the secret weapon some leaders are overlooking? In today’s fast-paced world, we’re taught to believe that the most successful leaders are the loudest, the boldest, and the most aggressive. But what if humility, often seen as a weakness, is actually the missi...

"Encouraging disagreement strengthens decision-making, challenges blind spots, and creates an environment where people feel heard." - Winnie da Silva

What if avoiding disagreement is actually holding you back? Most of us instinctively avoid conflict. We’re taught that disagreeing can damage relationships, create tension, or make us look difficult. But what if I told you that the way we approach disagreement could be the key to maki...

"Motivation starts with identity—when you believe in the story you’re telling yourself, the actions follow." - Nikhil Paul

Is it possible to lead with passion and effectiveness if you no longer feel connected to the business you're running? In this engaging conversation, I have with leadership coach Nikhil Paul, he dives deep into the heart of leadership, self-reflection, and sustainable business practices. Nikhil emphasizes the imp...

"When you align individual motivation with the broader mission, that’s when magic happens and teams thrive.” - James Thorman

What does it take to lead a team with purpose, ignite individual motivation, and build a thriving, high-performing culture? In this episode of Transformative Leadership Conversations, James Thorman, a seasoned leader with a wealth of experience from his time at A Place for Mom and other roles, joins me to dive...

"Leaders can't motivate people—and nor should they. But what you can do is foster an environment where intrinsic motivation can thrive." - Winnie da Silva

What if I told you that motivating your team isn’t your job? It sounds counterintuitive, right? As a leader, your instinct is to inspire your team to perform at their best—but real, lasting motivation comes from within. In this episode of Transformative Leadership Conversations, I...