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Transformative Leadership Conversations with Winnie da Silva
Winnie da Silva
116 episodes
1 week ago
Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.
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Management
Business,
Careers,
Entrepreneurship
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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 (20/116)
Transformative Leadership Conversations with Winnie da Silva
Tiny Experiments in Leadership Thinking with Winnie da Silva
“Leadership growth doesn’t have to come from huge reinventions. Often, it comes from tiny experiments.”Busyness has a sneaky way of convincing us that it equals importance - and for a long time, I let that idea drive how I measured my value as a leader. In this bonus episode, I’m sharing what happened when I decided to interrupt that pattern with one small, intentional experiment. No grand strategy. No perfectly mapped plan. Just 45 minutes a week to think - really think - and see what surfaced.You’ll hear me discuss:* How I realized I was buying into the belief that my leadership value is tied to productivity* Why I committed to a short, weekly strategic thinking practice and what I hoped it might change* How strange and uncomfortable it felt at first to sit with no agenda, no screen, and no clear outcome* Why even 30 minutes of protected thinking time turned out to be more than enough* How rest, reflection, and permission played a bigger role than I expected* What I noticed about my thinking carrying over and deepening between sessions* Why sticking to pen and paper helped me trust my own thinking instead of outsourcing it* How one meaningful conversation with a trusted colleague reshaped my strategic clarity* Why strategic thinking doesn’t have to be a solo activity to be effective* What consistency, accountability, and keeping the bar low actually made possibleResourcesWinnie 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)
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2 weeks ago
15 minutes 22 seconds

Transformative Leadership Conversations with Winnie da Silva
How Leadership Confidence Gets Tested with Winnie da Silva
“When leaders lose confidence, it’s usually traced back to these four patterns: the unknown, the comparison, the undermining relationship, and the identity transition.”Confidence doesn’t usually disappear overnight. More often, it slips away quietly, shaped by patterns we don’t always notice while we’re inside them. After two decades of coaching leaders, building teams, and watching incredibly capable people question themselves, I started to see the same confidence breakdowns show up again and again. In this episode, I’m wrapping up The Confidence to Lead series by sharing the four patterns I see most often when leadership confidence starts to erode and what it actually takes to rebuild it from the inside out.You’ll hear me discuss:* How operating in the unknown erodes confidence when expectations are unclear, success isn’t defined, and feedback feels vague or inconsistent* Why comparison quietly undermines leadership confidence, especially when we measure ourselves against someone else’s style, presence, or definition of success* How undermining relationships and low psychological safety can wear down even the strongest leaders over time* Why identity transitions - like promotions, role changes, or industry shifts - often trigger self-doubt, even when you’re fully qualified* Real client stories that show how these patterns play out in everyday leadership moments* The questions I use in coaching to help leaders identify which pattern might be impacting them most* Practical ways to rebuild confidence in each situation, without waiting for permission, validation, or perfect conditionsResourcesWinnie 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)
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3 weeks ago
26 minutes 23 seconds

Transformative Leadership Conversations with Winnie da Silva
The Confidence You Learn with Dr. Angela Stopper
“Confidence is a skill. It is a skill just like every other skill that we have, that we can use, that we practice.” - Dr. Angela StopperConfidence can feel so uneven. Solid in one moment and shaky in the next. It’s one of those topics that shows up in almost every leadership conversation I have, yet most of us still aren’t quite sure how it actually works. Is it innate? Is it something you earn? Or does it grow through experience?In this episode, I sit down with Dr. Angela Stopper, Chief Learning Officer at UC Berkeley, who has spent years looking at confidence from a completely different angle. Angela sees confidence as a skill - a set of competencies we can practice, strengthen, and shape so it feels authentic to who we are. Her model makes the entire idea of “being confident” feel far more doable and a lot less mysterious.You'll hear us discuss:* Why treating confidence as a skill makes it accessible to literally everyone* The six competencies in Angela’s model and how they work together* The many ways the “confidence gap” shows up and why it isn’t just a gender issue* How outside reactions, expectations, and bias can shape our sense of confidence* The pressure to not be “too much,” especially for women, and how Angela coaches people through that* The role courage plays in leadership and why it’s often misunderstood* The connection between confidence and making decisions, even when the outcome isn’t guaranteed* How mistakes and small experiments build resilience and help confidence grow over timeResourcesAngela Stopper on LinkedIn (https://www.linkedin.com/in/angela-stopper-ph-d-a75b0710/)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)
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1 month ago
43 minutes 12 seconds

Transformative Leadership Conversations with Winnie da Silva
The Confidence You Build with Julienne H. Silverman
“It’s not that you already know the answers or already are perfect at something, but that you believe that you can get there.” - Julienne SilvermanConfidence can look rock–solid from the outside… but inside, it’s usually a mix of courage, doubt, experience, improvisation, and a whole lot of personal growth. And sometimes the biggest boosts to our confidence come from the moments we’d never expect.In this episode, I sit down with investment banking executive Julienne (Julie) Silverman for a truly grounded and honest conversation about what confidence actually feels like and how it evolves over the course of a career. Julie shares stories from her early days managing the legendary New York restaurant Pastis all the way through her senior roles on Wall Street today, and she opens up about the shifts, pivots, and lessons that shaped her leadership.You’ll hear us discuss:* How Julie defines confidence in a way that feels surprisingly freeing and why it has nothing to do with perfection.* The unforgettable Courtney Love story that taught her how to handle pressure and trust her instincts long before she worked in finance.* What the “arc of confidence” looks like and why confidence often dips when you step into bigger, more challenging roles.* How she navigates ambiguity in entrepreneurial environments while keeping both daily decisions and long-term goals in view.* The subtle, gendered expectations around confidence at work and the small habits that help women show up with more presence.* Julie’s go-to advice for younger women: introduce yourself with your full name, take a literal seat at the table, and own your spot in the room.* Why being fully out at work has strengthened her leadership, and how authenticity creates deeper relationships and real confidenceResourcesJulienne H. Silverman on LinkedIn (https://www.linkedin.com/in/julienne-h-silverman-963894a/) | On the Web (https://www.pjtpartners.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/) | YouTube (https://www.youtube.com/@winniedasilvaleadership) | Email - winnie@winnifred.org (mailto:winnie@winnifred.org)
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1 month ago
45 minutes 13 seconds

Transformative Leadership Conversations with Winnie da Silva
Rest as a Leadership Strategy with Winnie da Silva
“We are not meant to force ourselves into monochromatic, one-tone grinds that look and feel the same every single day.” - Winnie da SilvaHigh-performing leaders love a good challenge, so here’s one: can you actually sit still without feeling guilty? Most of us can’t, and there’s a reason for that. Pushing through isn’t always strength, but sometimes the moment you slip into self-neglect without even noticing. In this episode, I wrap up our month-long series on “excellence without exhaustion” by taking a deeper look at how awareness, rhythm, and tiny experiments can shift the entire way we lead. I also share a personal conversation with my daughter that completely reframed how I think about rest… and honestly, it stopped me in my tracks.You’ll hear me discuss:* How my daughter’s off-hand comment revealed a deeply ingrained family belief that “doing” equals worth* Why rest can’t just be about recovering so you can work harder again* The difference between pushing through as a strength and pushing through as a liability* The subtle early signals our bodies give us when stress is building and why catching them matters* What natural biological rhythms look like and how they can guide smarter, more sustainable performance* How forcing our bodies to match our calendars erodes creativity, wisdom, and compassion* Why tiny experiments (not big overhauls) create real and lasting change* The simple nighttime practice I use to stop rumination in its tracks* How revitalization becomes an act of humility and even a spiritual reset* Questions you can start using today to notice your patterns, shift your rhythm, and build rest back into your leadershipWinnie 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)Learn More About Sapiens* Overview of Sapiens - A short video introduction to Sapiens and their mission to help people in intense jobs manage stress and sustain performance.* Video: The Diagnostics Journey - See what it’s like to go through the full Sapiens Stress & Resilience Diagnostic and Human Performance Journey.* Sneak Peek: Sapiens Workshop - Get a behind-the-scenes look at a real Sapiens workshop with a CFO team.Mentioned Studies* Impact of long exhales on down-regulating the nervous system and improving mood (https://pubmed.ncbi.nlm.nih.gov/36630953/)* Impact of microbiome composition on social decision making (https://pmc.ncbi.nlm.nih.gov/articles/PMC11093127/)* The connection between stress and empathy (https://www.sciencedirect.com/science/article/pii/S0149763422004924)* Link between empathy and inflammation (https://www.sciencedirect.com/science/article/abs/pii/S0889159124003131?via=ihub)Special Offer for ListenersJan-Philipp Martini, founder and CEO of Sapiens, is offering Transformative Leadership Conversations listeners a 20% discount on the Sapiens Stress & Resilience Diagnostic and Habit-Change Program, valid through the end of 2025.
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1 month ago
22 minutes 59 seconds

Transformative Leadership Conversations with Winnie da Silva
The Biology Behind Effective Leadership with Martin Redigolo and Jan-Philipp Martini
"Chronic stress is anti-correlated with all the things you want to have as a leader. It's anti-correlated with empathy, it's anti-correlated with creativity, and it's anti-correlated with co...
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1 month ago
59 minutes 28 seconds

Transformative Leadership Conversations with Winnie da Silva
The Science of Sustainable Success with Jan-Philipp Martini
“Sapiens is an idea, first of all, that we can perform at a high level and at the same time work in harmony with our biology.” - Jan Philipp MartiniHave you noticed some people seem to thrive under pressure while others slowly burn out? What if stress isn’t the enemy but the secret ingredient to lasting performance? In this episode, I sit down with Jan-Philipp Martini, founder and CEO of Sapiens, to explore what really happens when ambition collides with biology. Jan shares how his own health crisis became the turning point that led him to rethink everything he knew about high performance. Together, we unpack the science behind stress, why it’s not the villain we’ve made it out to be, and how tuning into your body’s signals can transform the way you lead and live.You’ll hear us discuss:* Jan’s journey from high-pressure management consulting to creating a company that helps leaders measure and manage stress through data* What his diagnosis with type 1 diabetes taught him about the hidden cost of “pushing through”* Why stress itself isn’t bad and how understanding your body’s natural rhythms can actually unlock better performance* The difference between restlessness and fatigue, and what those states reveal about your biology* How stress shows up in the body - long before burnout hits - and the early signs we tend to ignore* The three stress archetypes (green, yellow, orange) and what they say about where you are on the stress spectrum* How leaders can catch weak signals - like irritability, gut issues, or sleeplessness - before they turn into full-blown problems* Simple ways to sync your daily habits with your body’s natural rhythm so you can sustain excellence without exhaustionResourcesJanPhilipp Martini on Sapiens (https://www.be-sapiens.com/) | LinkedIn (https://www.linkedin.com/in/janphilippmartini/?originalSubdomain=de)Book a 15-minute free demo consultation - Link (https://calendly.com/janphilipp-martini-sapiens/15-min-demo?month=2025-11)Research: How We Measure Stress Using Body Data and Self-Assessments: Read here (https://www.be-sapiens.com/research-posts/how-we-measure-stress-using-body-data-and-self-assessments?utm_source=chatgpt.com)Learn More About Sapiens • Overview of Sapiens (https://www.be-sapiens.com/video/sapiens-company-overview): A short video introduction to Sapiens and their mission to help people in intense jobs manage stress and sustain performance. • Video: The Diagnostics Journey (https://www.be-sapiens.com/videos/sapiens-individual-offering-human-performance-journey): See what it’s like to go through the full Sapiens Stress & Resilience Diagnostic and Human Performance Journey. • Sneak Peek: Sapiens Workshop (https://www.be-sapiens.com/video/sneak-peak-into-a-sapiens-workshop-with-a-cfo-team): Get a behind-the-scenes look at a real Sapiens workshop with a CFO team. Mentioned Studies• Impact of long exhales on down-regulating the nervous system and improving mood (https://pubmed.ncbi.nlm.nih.gov/36630953/) • Impact of microbiome composition on social decision making (https://pmc.ncbi.nlm.nih.gov/articles/PMC11093127/) • The connection between stress and empathy (https://www.sciencedirect.com/science/article/pii/S0149763422004924) •
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2 months ago
51 minutes 6 seconds

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.
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2 months 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)
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2 months 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)
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2 months 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)
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2 months 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)
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3 months 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
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3 months 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)
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3 months 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)
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4 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
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4 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)
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4 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
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5 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)
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5 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/)
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5 months ago
51 minutes 6 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.