Transformative Leadership Conversations with Winnie da Silva

"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...

"Diversity of thought is very powerful. I aggressively seek out people that don’t think like me and are polar opposites of me. That’s the only way to pull yourself out of your own corner." - Mauhan Zonoozy



What if the biggest barrier to innovation isn’t a lack of ideas—but a fear of permission? In this episode of Transformative Leadership Conversations, I sat down with Mauhan Zonoozy, a strategic advisor and expert in innovation an...

What if innovation isn’t just for a select few, but something every single person can access and contribute to? In this episode of Transformative Leadership Conversations, I had the chance to chat with Sandy Fershee, the Head of Design & User Experience at Audible. Sandy shared some truly inspiring thoughts about innovation—how it’s not something reserved for just a select few, but something that everyone can contribute to. We ...

What if the biggest barrier to innovation within your team or organization is you? In this episode, I’m diving into the heart of innovation—what it means for leaders and how we can create an environment that allows it to thrive. I explore the essential role that leaders play in driving meaningful innovation and reflect on how we can overcome the distractions and barriers that keep us from unlocking our full creative potential.

In th...

What’s your story, and how does it shape your brand? In this episode of Transformative Leadership Conversations, I sit down with Maria Ho-Burge, Vice President of Communications at TuneCore, to dive deep into the art of building a personal and professional brand. Maria shares how authenticity, storytelling, and strategy come together to create a brand that not only stands out but also drives value in any industry.

From her work in t...

What does it take to drive change in a male-dominated industry while staying true to your vision? In this episode of Transformative Leadership Conversations, I sit down with Andreea Gleeson, CEO of TuneCore, to hear her remarkable story. Andreea shares how she transitioned from retail to music, the challenges she’s faced as a woman in leadership, and her mission to empower artists at every level of their careers. From tackling gend...

How do people really see you, and does that match who you want to be? In this episode of Transformative Leadership Conversations, I take a close look at what it means to shape your leadership brand authentically. Through stories from real clients and practical advice, I’ll show you how to shape and evolve your brand to resonate and stand out in ways that genuinely reflect you.

Listen in as I discuss:

• Defining Your Leadership Bran...

How do I define success—and how does that shape the decisions I make? In this episode of Transformative Leadership Conversations, I have the pleasure of chatting with Cherie Hu, a music industry expert and the founder of Water & Music. Together, we dive into decision-making in both creative and business landscapes, exploring how our interpretations of success can shape our paths and the strategies we choose.

You’ll here them dis...

What happens when the very decisions you make as a leader cause unintended ripple effects throughout your organization? In this episode of Transformative Leadership Conversations, I sit down with Prita Kumar to explore the complex balance of short-term goals, long-term planning, and the law of unintended consequences in leadership. Prita shares her experience in managing teams without overwhelming them, how she thinks about qualita...