Transformative Leadership Conversations with Winnie da Silva

“Every challenge you face builds your leadership muscle for the next one.” - Winnie da Silva What makes someone take a leap with no safety net - and end up building a life and career more meaningful than they ever imagined? Twenty years ago, I turned down two job offers, quit my job, and had no real plan - just an 18-month-old baby, a husband between startups, and a mortgage. Looking back now, it...

‘’What’s inspiring is seeing MBA students shift from seeing leaders on a pedestal to realizing leadership is about collaboration and bringing people along.” - Gerard Beenen Do the next generation of business leaders think about leadership in a totally different way? What if it wasn’t about authority, charisma, or titles - but about building trust, creating clarity, and inspiring people to move tog...

“If you’re not listening to your customers, to your students, to your users, then you run the risk of using generic best practices that work in situation X, but might totally face plant in situation Y." - Elliot Felix Is the future of higher education about piling on more programs, services, and systems, or about focusing on what truly helps students succeed? And how often do colleges and universi...

“For leaders today, the question isn’t just how to sustain our institutions, but how to create reasons for hope in the field.” - Gwendolyn Freed What does it really take to step into the presidency of a college during one of the most complex and challenging times for higher education and the arts? And how do you lead with both strength and hope when the pressures - political, cultural, and financi...

“In higher education, success can’t always be measured in numbers. Leaders are shaping something far more enduring: global citizens who will contribute to the world.” - Winnie da Silva What happens when the very institutions built to shape future leaders are suddenly shaken to the core? Higher education is facing pressures unlike anything we’ve seen before - political battles, the rise of generati...

“People with ADHD aren’t asking for sympathy. They’re saying: here are my pain points and here’s what I need in order to be successful.” - Amy Shilliday What if the very traits we often label as “challenges” are actually hidden superpowers? And what would it look like if leaders truly understood how to support neurodivergent employees - not just to cope, but to thrive? In this episode of Transform...

"ADHD isn't a weakness or a superpower. It's just an operating system. And when you learn how to work inside your own operating system, you can actually become a power user." – Stephanie Scheller What if the quirks of your brain weren’t obstacles to overcome but the foundation of how you build teams, businesses, and even your own self-confidence? What if the very things you thought were holding yo...

"When we understand how our minds work—and honor the minds of others—we lead better." - Winnie da Silva What if everything you’ve been told about ADHD only told half the story? What if the very traits that make it hard for you to stay on task could also be the ones that make you an incredible leader? In this opening episode of my ADHD and leadership series, I’m diving into what ADHD really is, how...

"Immigrant entrepreneurs are powerful at reframing. Reframing rejection. Reframing failure. Reframing their past." - Dr. Neri Karra Sillaman What if the hardest chapter of your life - the one where you lost everything - turned out to be the thing that shaped you into the leader you were always meant to be? In this episode, I talk with Dr. Neri Karra Sillaman, whose journey from child refugee to Ox...

"An unconventional entrepreneur has been hustling before the idea even came. It's their way of life." - Arjita Sethi What if the thing that makes you feel like an outsider is actually the reason you're built to lead? In this episode, I talk to Arjita Sethi - an immigrant entrepreneur, educator, and founder of New Founders School. From growing up in Delhi and helping run a school with her mom at 16...

“There is a knowing in me that beneath that cultural layer, we’re the same. It sounds so obvious, but it has made me show up in different ways.”  - Anna Gudmundson What does it really take to lead with purpose when you’re building a life - and a business - in a country that’s not your own? In this episode, I sit down with Anna Gudmundson, CEO of Sensate and a global tech entrepreneur whose story s...

“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...

“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 b...

"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 invi...

“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 rew...

"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....

‘’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 F...

"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 lea...

"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 episod...

"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...

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 pers...

“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,...

"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 Transfo...

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 t...

“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'...