Home
Categories
EXPLORE
True Crime
Comedy
Society & Culture
Business
Sports
History
Music
About Us
Contact Us
Copyright
© 2024 PodJoint
00:00 / 00:00
Sign in

or

Don't have an account?
Sign up
Forgot password
https://is1-ssl.mzstatic.com/image/thumb/Podcasts221/v4/79/9f/a8/799fa819-ce10-00ef-9968-e8eadd77f9de/mza_6824674188042034106.jpg/600x600bb.jpg
Transformative Leadership Conversations with Winnie da Silva
Winnie da Silva
109 episodes
4 days ago
Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.
Show more...
Management
Business,
Careers,
Entrepreneurship
RSS
All content for Transformative Leadership Conversations with Winnie da Silva is the property of Winnie da Silva and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.
Show more...
Management
Business,
Careers,
Entrepreneurship
Episodes (20/109)
Transformative Leadership Conversations with Winnie da Silva
Caring Too Much at Work with Martin Redigolo
“The stress I carried slowed me down — I couldn’t think clearly, and I didn’t recognize myself anymore.” - Martin RedigoloWhat if the very thing that makes you successful is also what’s slowly breaking you down? In this episode, I sit down with design and business leader Martin Redigolo for a raw, honest conversation about stress - not just the kind that keeps you up at night, but the kind that shapes you as a leader. From the high-intensity worlds of Deloitte, BCG, and Manion to his personal turning points, Martin opens up about how ambition, responsibility, and caring deeply for others can collide. This one’s about learning to lead without losing yourself.You’ll hear me discuss:* How Martin’s early career excitement blurred the line between passion and pressure and why it took years to notice the difference* What happens when your strengths as a caring, people-focused leader start to work against you* The tension between wanting to do right by others and holding yourself to impossible standards* How disconnecting from your core values (like fairness and care) can quietly turn stress into self-doubt* The moment Martin realized he was “standing in his own way” and what it taught him about rebuilding trust in himself* Why structure, trusted people, and simple routines can be lifelines when stress takes over* The one piece of coaching advice that completely changed how he leads under pressureResourcesMartin Redigolo on Web (https://martinredigolo.com/) | LinkedIn (https://www.linkedin.com/in/martinredigolo/?originalSubdomain=es)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)Get 20% off Sapiens’ four-month Stress and Resilience Diagnostic and Habit Change Program—which includes biological stress testing and expert coaching - by using the code TLC at www.be-sapiens.com (https://www.be-sapiens.com/), with the offer valid through the end of 2025.
Show more...
4 days ago
47 minutes 11 seconds

Transformative Leadership Conversations with Winnie da Silva
The Hardest Leadership Question with Winnie da Silva
“People do change - sometimes by choice, sometimes by necessity, but always through connection.” - Winnie da SilvaCan people really change? Or are we just fine-tuning the version of ourselves that already exists? After 20 years of coaching and consulting leaders, I still find myself coming back to this question because it’s one that sits at the heart of every transformation story I’ve ever witnessed. In this final episode of my 20-year celebration series, I’m pulling back the curtain on what I’ve learned about how change really happens and why we rarely do it alone.You’ll hear me discuss:* The real question behind “Can people change?” and why it often starts with asking if I can change.* What it actually means to change how you show up, not who you are.* The story of “Marty,” a quiet executive who learned to project confidence without becoming someone he’s not.* The four kinds of change - intentional transformation, deliberate reinvention, situational upheaval, and identity disruption - and how they show up in real life.* Why relationships are the scaffolding of change - the people who stretch us, challenge us, and hold up the mirror we sometimes need.* Two powerful stories of leaders who transformed - one by choice, one through challenge - and what their journeys reveal about reclaiming your own story.* How true change starts as an internal shift but becomes real only through connection.ResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
Show more...
1 week ago
14 minutes 49 seconds

Transformative Leadership Conversations with Winnie da Silva
The Lie (Almost) Every Leader Believes with Winnie da Silva
“Leadership isn’t about how much you do. It’s about how we think, how we connect, and how courageously we act on what really matters.” - Winnie da SilvaIs the biggest lie you’ve been told about leadership the one you’ve been telling yourself? The one that says your worth as a leader is measured by how much you do - how productive, busy, and available you are. In this episode, I’m pulling back the curtain on one of the most common and costly leadership lies: that doing determines your value. I’ll share what it’s really costing us - our clarity, creativity, and connection - and how we can start leading from a place of deep thinking instead of constant doing.You’ll hear me discuss:* Why leaders (myself included) struggle to let go of the need to constantly prove their value through action* How our obsession with busyness is quietly draining our best ideas and strategic thinking* What deep thinking really looks like and how it can transform not only how we lead, but how we live* How “white space” can become one of the most powerful leadership tools on your calendar* The simple, practical steps I’m taking to carve out time to think (and how you can experiment with your own version)* Why leadership isn’t something we prove. It’s something we practiceResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
Show more...
2 weeks ago
20 minutes 57 seconds

Transformative Leadership Conversations with Winnie da Silva
Celebrating 20 Years of Transformative Leadership with Winnie da Silva
“Every challenge you face builds your leadership muscle for the next one.” - Winnie da SilvaWhat 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 was one of the best (and scariest) decisions I’ve ever made.In this episode, I open up about that journey. How I went from social work to corporate consulting to entrepreneurship and what I’ve learned about leadership, growth, and trusting yourself when the path ahead is anything but clear.You’ll hear me discuss:* Why great leadership always starts on the inside and how real change begins with ourselves* The pivotal moment that pushed me to walk away from “safe” and build something on my own terms* What it really took to transition from social work to business consulting (and why theater skills helped!)* How saying “no” to the wrong opportunities can open the door to the right ones* The lessons I’ve learned from launching my own podcast - imperfectly, impatiently, and all on my own* Why learning to take the long view has shaped everything from my client relationships to my definition of successResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
Show more...
3 weeks ago
32 minutes 21 seconds

Transformative Leadership Conversations with Winnie da Silva
MBA Students Rethink Leadership with Gerard Beenen
‘’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 BeenenDo 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 together toward something bigger? In this special bonus episode, I sit down with Gerard Beenen, professor of management and leadership consultant, to explore how MBA students are rethinking leadership in real time. Together, we connect their reflections to two powerful frameworks - transformational leadership and self-determination theory - and talk about what those ideas mean for anyone leading today.This isn’t just theory from the classroom. You’ll hear directly from Gerard’s MBA students at Carnegie Mellon as they share how their definitions of effective leadership have shifted during their studies. Their voices are honest, insightful, and sometimes surprising - and they might challenge some of the assumptions you’ve been carrying about what leadership really is.In this episode, you’ll hear:* The surprising moment in history when leadership research almost disappeared and how it came back stronger than ever* Why the old “great person” theory of leadership still lingers in how we think about leaders today* The full range of leadership styles, from laissez-faire to transactional to transformational, and why transformational leadership continues to inspire change* The four “I’s” of transformational leadership and how they show up in everyday leadership moments* Real stories from MBA students as they move from task-orientation and authority toward collaboration, trust, and long-term purpose* How transformational leadership connects directly to self-determination theory - one of the most influential ideas in motivation research* The three core psychological needs we all share (autonomy, competence, and relatedness) and how they shape motivation at work* Why it’s not just about motivating your direct reports - you can apply these theories in 360 degrees with your peers, your leaders, and across your whole organization* Practical ways to create conditions where people feel empowered, inspired, and aligned without putting yourself on the hook to “motivate everyone” all the timeResourcesGerard Beenen on Cal State Fullerton (https://experts.fullerton.edu/expert?ExpertID=643) | LinkedIn (https://www.linkedin.com/in/gerard-beenen-ph-d-4b073/) | Academia.edu (https://independent.academia.edu/GerardBeenen)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
Show more...
1 month ago
1 hour 13 minutes 14 seconds

Transformative Leadership Conversations with Winnie da Silva
Prototyping Better Leadership with Elliot Felix
“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 FelixIs 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 universities leap to solutions before asking what students actually need?In this episode of Transformative Leadership Conversations, I sit down with Elliot Felix, author of The Connected College, to explore what higher ed leaders - and really, leaders everywhere - can learn about breaking silos, designing better student experiences, and leading through complexity and change. Elliot brings stories from campuses across the country, along with practical tools and a fresh way of thinking about leadership.You’ll hear us discuss:* Why “less with more” helps institutions focus resources on what makes the biggest difference for students* How everyday habits of prioritization create clarity for leaders, faculty, and staff* The double diamond framework and how defining the right problem first improves student outcomes* What design thinking looks like when universities listen to students and design around their experience* How prototyping new programs can reduce risk and build confidence before scaling up* The danger of overwhelming faculty and staff with too much information, and how to strike a healthier balance* The leadership myth Elliot once believed and how working with students and campuses changed his perspectiveResourcesElliot Felix on the Web (https://www.elliotfelix.com/) | The Connected College Book (https://www.elliotfelix.com/connectedcollege) | The Connected College Podcast (https://www.elliotfelix.com/podcast) | LinkedIn (https://www.linkedin.com/in/elliotfelix/)Winnie da Silva on
Show more...
1 month ago
48 minutes 12 seconds

Transformative Leadership Conversations with Winnie da Silva
Hope and Leadership in Education with Gwendolyn Freed
“For leaders today, the question isn’t just how to sustain our institutions, but how to create reasons for hope in the field.” - Gwendolyn FreedWhat 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 financial - are constantly shifting?In this episode of Transformative Leadership Conversations, I sit down with Dr. Gwendolyn Freed, the new president of the Minneapolis College of Art and Design (MCAD). Gwen brings a remarkable mix of experiences across higher education, nonprofit leadership, journalism, and the art.You’ll hear us discuss:* The surprising shift that happens when people see “your presidency walk into the room” rather than just you* How Gwen thinks about balancing MCAD’s long history with its future identity and growth* What it really means to listen to and serve such a wide range of stakeholders* The challenges and opportunities of leading an arts and design college in today’s political and cultural climate* Why Gwen finds so much hope in students and their creativity* Her take on AI - where it doesn’t belong and where it absolutely can spark new possibilities* The leadership lessons she’s learned that translate far beyond higher educationResourcesGwendolyn Freed on MCAD (https://www.mcad.edu/) | LinkedIn (https://www.linkedin.com/in/gwendolynfreed/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
Show more...
1 month ago
34 minutes 51 seconds

Transformative Leadership Conversations with Winnie da Silva
Lessons from Higher Education for Every Leader with Winnie da Silva
“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 SilvaWhat 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 generative AI, ongoing questions of safety, and cultural divides that threaten its very purpose. The truth is, these challenges don’t just affect universities; they mirror the pressures leaders everywhere are up against. So what can we learn from the people leading in higher ed right now?You’ll hear me discuss:* Why higher education has become such a critical and contested space in our country’s future* How generative AI is raising new questions about the very purpose of learning* The impact of campus safety concerns and the rise of school violence on students’ sense of belonging* The erosion of healthy debate and why academic freedom matters more than ever* The political attacks shaping what can and cannot be taught in classrooms* Four big leadership lessons I’ve seen firsthand from working with presidents, professors, and their teams* A preview of the three incredible guests joining me this month to share their own journeys and insightsResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) I Email - winnie@winnifred.org (mailto:winnie@winnifred.org)Studies referenced:Americans' Confidence in Higher Education Down Sharply (https://news.gallup.com/poll/508352/americans-confidence-higher-education-down-sharply.aspx)How to Save the American University (https://www.theguardian.com/us-news/ng-interactive/2025/aug/24/how-to-save-the-american-university)Students Hate Them. Universities Need Them. The Only Real Solution to the A.I Cheating Crisis (https://www.nytimes.com/2025/08/26/opinion/culture/ai-chatgpt-college-cheating-medieval.html?algo=combo_lda_unique_clicks_decay_96_50_ranks&block=5&campaign_id=142&emc=edit_fory_20250901&fellback=false&imp_id=666394187408387&instance_id=161690&nl=for-you&nlid=10756530&pool=fye-rotating-opinion-ls&rank=3®i_id=10756530&req_id=8171950298959948&segment_id=205055&surface=for-you-email-rotating-X&user_id=65493e3607c2eaa50cc96d8ed587ef3f&variant=0_best_algo)The Typical College Student Is Not Who You Think (https://www.nytimes.com/2025/08/25/us/us-typical-college-student.html?smid=nytcore-ios-share&referringSource=articleShare)
Show more...
2 months ago
16 minutes 51 seconds

Transformative Leadership Conversations with Winnie da Silva
Making Learning Neurodivergent-Friendly with Amy Shilliday
“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
Show more...
2 months ago
51 minutes 29 seconds

Transformative Leadership Conversations with Winnie da Silva
ADHD Leadership Operating System with Stephanie Scheller
"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 SchellerWhat 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 you back in leadership were actually the key to leading better?That’s exactly the kind of reframing my guest, Stephanie Scheller, has done. Stephanie is an entrepreneur, violinist, author, and the founder of Grow Disrupt. She’s also a leader who discovered later in life that ADHD had shaped everything about how she worked, led, and built her company. Instead of fighting it, she’s learned to design her business and leadership style around the way her brain works - and she’s sharing what that looks like in real life.You’ll hear us discuss:* Why ADHD isn’t a weakness or a superpower, but an operating system you can learn to master* How Stephanie spotted her own patterns and built “bumpers” into her life and work to keep moving forward* The role of grace, anxiety, and depression in her journey - and the tools she uses when things start to spiral* The idea of “frozen tater days” and how her team uses this language to normalize and support each other* Practical ways leaders can support neurodiverse team members without lowering performance expectations* What it looks like to build events, businesses, and leadership practices that work with your brain, not against it* How shifting perspective from “fixing” to “designing for your brain” can change the way you lead and liveResourcesStephanie Scheller on LinkedIn (https://www.linkedin.com/in/stephaniescheller/) | Grow Disrupt (https://www.growdisrupt.com/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | (https://www.youtube.com/@winniedasilvaleadership)
Show more...
2 months ago
52 minutes 11 seconds

Transformative Leadership Conversations with Winnie da Silva
ADHD and the Way You Lead with Winnie da Silva
"When we understand how our minds work—and honor the minds of others—we lead better." - Winnie da Silva
Show more...
2 months ago
24 minutes 26 seconds

Transformative Leadership Conversations with Winnie da Silva
Frying in Your Own Oil with Dr. Neri Karra Sillaman
"Immigrant entrepreneurs are powerful at reframing. Reframing rejection. Reframing failure. Reframing their past." - Dr. Neri Karra SillamanWhat 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 Oxford professor and global entrepreneur is nothing short of incredible. Her work has appeared in BBC, Forbes, Financial Times, Harvard Business Review, CNBC and others. She's also the author of Pioneers: Eight Principles of Business Longevity from Immigrant Entrepreneurs, a book that captures both her lived experience and her research into what really helps immigrant-led businesses thrive - not just survive.You'll hear us talk about:* What it was like being forced to flee Bulgaria as a child, and how that shaped her identity and worldview* How growing up under a regime that tried to erase her culture made her fiercely committed to authenticity and purpose* Why immigrant entrepreneurs often build stronger, longer-lasting businesses - and why that’s not a coincidence* What “frying in your own oil” means, and why it’s such a powerful mindset for building something from scratch* How reframing rejection and failure is a common thread in the stories of successful immigrant founders* The huge role community, trust, and relationships play in business longevity - and why these things are often overlooked* Why chasing profit isn’t the priority for many immigrant entrepreneurs - and what they focus on instead* The kind of leadership that puts people, not ego, at the center - and why that matters now more than everResourcesNeri Karra Sillaman on (https://www.nerikarrasillaman.com/)Website (https://www.nerikarrasillaman.com/) | (https://www.linkedin.com/in/neri-karra-sillaman/?originalSubdomain=fr)LinkedIn (https://www.linkedin.com/in/neri-karra-sillaman/?originalSubdomain=fr) | (https://www.nerikarrasillaman.com/books/pioneers)Neri's book: Pioneers: 8 Principles of Business Longevity from Immigrant Entrepreneurs (https://www.nerikarrasillaman.com/books/pioneers)
Show more...
3 months ago
54 minutes 27 seconds

Transformative Leadership Conversations with Winnie da Silva
The Power of Unconventional Entrepreneurs with Arjita Sethi
"An unconventional entrepreneur has been hustling before the idea even came. It's their way of life." - Arjita SethiWhat 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, to building a startup in Silicon Valley while navigating the U.S. immigration system, Arjita’s story is a powerful mix of hustle, heart, and hard-earned wisdom. We get into what it really takes to build something when you don’t come from privilege, and how being an immigrant gives you a different kind of edge - one that’s rooted in adaptability, resourcefulness, and the ability to keep going no matter what.You'll hear us discuss:* How growing up as an immigrant shaped the way Arjita leads, takes risks, and thinks like a founder* Why some of the best entrepreneurs out there don’t look or sound like what the startup world expects* The real superpowers immigrant founders already have - even if they don’t know it yet* How she burned out chasing the “Silicon Valley dream” and what she had to unlearn* What it’s like to build a business under constant visa pressure, and why that stress doesn’t get talked about enough* How New Founders School is helping underestimated entrepreneurs turn their lived experience into leadershipResourcesArjita Sethi on New Founder School (https://newfounderschool.com/) | Arjitha's Advantage Program (https://newfounderschool.com/advantage-program/) | LinkedIn (https://www.linkedin.com/in/arjitasethi/)
Show more...
3 months ago
51 minutes 6 seconds

Transformative Leadership Conversations with Winnie da Silva
Leading with a Global Lens with Anna Gudmundson
“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 GudmundsonWhat 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 spans six countries and countless transformative lessons. We explore what it means to lead as an immigrant, how to build a business without losing yourself, and why cultivating nervous system resilience might be the most overlooked leadership strategy today. Anna’s clarity, humility, and global lens make this conversation both grounding and expansive.You'll hear us discuss:* How Anna's early childhood in rural Africa shaped her core belief that "beneath that cultural layer, we're the same"* Her journey from Sweden to France, Spain, London, and eventually Los Angeles - and how each culture revealed something new about leadership and herself* What it means to create a startup culture rooted in presence, intention, and human connection, not just productivity* Why self-awareness and adaptability are non-negotiables for leading diverse, high-performing teams* The emotional cost of immigration and how Anna deliberately builds belonging in new environments* How Sensate helps people calm their nervous systems through infrasonic sound - and why Anna believes calming the body is foundational to leadership* The challenge of building company culture while fundraising, and how she uses values to guide everyday decisions* A refreshing take on feedback, safety, and why we don’t need to be liked to be effective leadersResourcesAnna Gudmundson on Sensate (https://www.getsensate.com/?srsltid=AfmBOooCS7MKItl8hQlUW61e7OaBjYWMj9n7p52Hm3Yk-3_s90eG61sF&variant=40503515250777) | Sensate Instagram (https://www.instagram.com/mysensate/reels/) | LinkedIn (https://www.linkedin.com/in/annakg/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) |
Show more...
3 months ago
58 minutes 3 seconds

Transformative Leadership Conversations with Winnie da Silva
Immigrants Built This 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 our national identity. As we celebrate America’s 249th birthday, I reflect on our roots as a nation of risk-takers and builders, and why the immigrant experience may just hold the most valuable leadership lessons of all. You’ll hear stories from my own family, eye-opening statistics, and a rich preview of three extraordinary women leaders joining the podcast this month.You'll hear me discuss:* Why America’s business roots run deeper than the Mayflower and how commerce, not just freedom, shaped our beginnings* How immigrant entrepreneurs today are driving business innovation and economic growth* What history gets wrong (or leaves out) about our “founders” and how that continues to shape opportunity* The four essential leadership traits every entrepreneur must master and why immigrants might be uniquely equipped to embody them* Powerful personal stories from my husband’s family and their multigenerational legacy of business-building in the U.S.* How resilience, adaptability, a growth mindset, and comfort with risk are more than buzzwords - they’re survival skills* What you can expect from upcoming conversations with three phenomenal immigrant women leadersResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | Email - winnie@winnifred.org
Show more...
4 months ago
19 minutes 3 seconds

Transformative Leadership Conversations with Winnie da Silva
Coaching Teens into Leadership with Lorraine Connell
“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 ConnellAre 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 with Lorraine Connell, former chemistry teacher turned teen leadership coach and founder of Peers Not Fears. Lorraine shares how her own experience of feeling “average” in school shaped her deep commitment to redefining leadership for young people. Together, we explore what happens when we empower teens before they’re handed official titles and how we can help them develop confidence, decision-making, and real leadership skills - long before they enter the workforce.You’ll hear us discuss:* How our myths around leadership - like needing a title or being perfect - hold kids (and adults) back* Why Lorraine believes the only true requirement for leadership is the ability to make a decision* The damage caused when we make student leaders into role models who aren’t allowed to fail* How mistakes (including Lorraine’s own) became the turning point for creating Peers Not Fears* The power of peer mentoring and why it’s more impactful than top-down leadership* Why confidence and leadership are inseparable - and how labeling kids can stall both* What leadership development actually looks like between ages 12 and 16* How games, group coaching, and creative challenges open teens up to growth* What adults need to remember about owning mistakes and modeling leadership* How to reframe leadership not as a ladder—but as something wide enough for everyoneResourcesLorraine Connell on (https://www.peers-not-fears.com/)Peers not Fears (https://www.peers-not-fears.com/) | (https://www.facebook.com/groups/peersnotfears)''Leadership for Our Kids!'' Facebook Group (https://www.facebook.com/groups/peersnotfears) | (https://www.peers-not-fears.com/teen-leadership-books)
Show more...
4 months ago
47 minutes 32 seconds

Transformative Leadership Conversations with Winnie da Silva
Teens Take on Leadership with Winnie da Silva
"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 SilvaCould 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, unfiltered thoughts on leadership - what it is, what it isn’t, and what they would change in the world if they were in charge. Their answers surprised me, inspired me, and reminded me just how powerful honest conversation can be.You will hear:* How today’s teens define great leadership through traits like empathy, kindness, and flexibility* Why many young people believe being feared or cold isn’t necessary - or even effective - as a leader* How the myth of “born leaders” is being firmly rejected by this generation* What gives Gen Z hope, and why justice, equality, and inclusion top their list of priorities* How students would lead change today - from political reform to creating unity in divided communities* Reflections on how media, culture, and current events are shaping young people’s ideas of power and corruption* A heartfelt wrap-up conversation with my daughter Aradhana da Silva on what her generation truly expects from leadersResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | Email - winnie@winnifred.org
Show more...
4 months ago
20 minutes 6 seconds

Transformative Leadership Conversations with Winnie da Silva
Next-Gen Views on Leadership with Winnie da Silva
“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 SilvaIs 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 Transformative Leadership Conversations, I talk about how our next generation of leaders - specifically Gen Z - is reshaping what leadership looks like from the ground up. From their desire for trust and transparency to their rejection of traditional management roles, Gen Z is showing us a very different vision of what it means to lead and be led. Maybe it's time we listened a little more closely.You'll hear me discuss:* What shaped Gen Z’s leadership perspective, including a timeline of major global events that defined their coming of age* How growing up in constant instability impacts what they want from leaders at work* Key findings from three major studies on Gen Z and leadership, and what those results reveal about trust, vulnerability, and empowerment* Why Gen Z is stepping away from middle management, and what “conscious unbossing” actually means* How companies say they value people leadership but often fail to show it through actions, compensation, or training* What the IKEA peg analogy reveals about the invisible, underestimated work of leading people* Two practical shifts we can make to better support emerging leaders today and redefine what leadership growth looks likeResourcesWinnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | Email - winnie@winnifred.org
Show more...
5 months ago
15 minutes 2 seconds

Transformative Leadership Conversations with Winnie da Silva
Listening as a Leadership Strategy with James Misner
"I think we overestimate the importance of knowing and underestimate the power of listening." - James MisnerWhat 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 and inspiring. James pushes us to rethink our assumptions about helping, belonging, and transformation — and why presence might just be more powerful than any plan. This episode is a call to slow down, to stay curious, and to build something deeper than solutions: real human connection.You’ll hear us discuss:* Why belonging isn’t just a warm feeling but a foundational need that must come before trust, belief, or any lasting change.* How systems that focus on outcomes instead of relationships can unintentionally harm the very people they are meant to support.* The importance of being willing to walk with someone through their pain and uncertainty, rather than trying to rescue them with quick fixes.* What can shift when we stop treating people as problems to solve and start seeing them as neighbors with stories, strengths, and dignity.* James’s personal journey of letting go of the pressure to always have the right answer and choosing instead to offer presence and patience.* How discomfort and tension can be invitations to stay and engage more deeply, rather than reasons to step back.* The quiet but radical impact of showing up consistently, without an agenda, simply to let someone know they’re not alone.ResourcesJames Misner on The Kipos Group (https://thekiposgroup.com/) | LinkedIn (https://www.linkedin.com/in/jamesmisner/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) | Substack (https://winniedasilva.substack.com/) | Email - winnie@winnifred.org
Show more...
5 months ago
39 minutes 28 seconds

Transformative Leadership Conversations with Winnie da Silva
Power, Dignity, and Crisis Leadership with Rebecca Vander Meulen
‘’Even in a non-profit context, issues of sharing power and mutual respect and dignity are essential and not universal.” - Rebecca Vander MeulenWhat 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 two decades working in global health, faith-based development, and cross-sector collaboration—from launching HIV and malaria programmes in rural Mozambique to running initiatives for people returning home after incarceration in New York City. Her leadership blends humility, deep empathy, and strategic thinking in some of the world’s most complex and under-resourced environments.You'll hear us discuss:* Why waiting for full clarity before communicating is a luxury leaders can’t afford in crisis—and how honest, imperfect communication builds more trust than silence.* How the sudden dismantling of USAID funding has devastated public health systems globally, and why leaders like Rebecca are having to reimagine their strategies on the ground with little information and no time.* The importance of recognising how power—whether in a community, a boardroom, or a rural health clinic—operates subtly, and how sharing it must be an intentional, ongoing process.* What it means to lead with purpose when your work is directly tied to life and death, and how personal connection—not metrics or strategies—often becomes the true driver of lasting impact.* How Rebecca’s years in remote Mozambique taught her not only how to mobilise local expertise but also how to navigate and build trust in completely different systems, including the private equity world in Manhattan.* Why the best social impact work isn’t born out of obligation or abstract logic, but out of deep personal passion—and how to find your own way into the work that truly matters to you.ResourcesRebecca Vander Meulen on LinkedIn (https://www.linkedin.com/in/rebecca-vander-meulen-150094156/) | J.C.Flowers Foundation (https://www.jcflowersfoundation.org/)Winnie da Silva on LinkedIn (https://www.linkedin.com/in/winnie-da-silva-1b8414/) | On the Web (https://www.winniedasilva.com/) |
Show more...
5 months ago
41 minutes 12 seconds

Transformative Leadership Conversations with Winnie da Silva
Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.