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 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 success

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

‘’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 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 time

Resources

Gerard Beenen on Cal State Fullerton | LinkedIn | Academia.edu

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

“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 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 perspective

Resources

Elliot Felix on the Web | The Connected College Book | The Connected College Podcast | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

“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 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 education

Resources

Gwendolyn Freed on MCAD | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

“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 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 insights

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube I Email - [email protected]

Studies referenced:

Americans' Confidence in Higher Education Down Sharply

How to Save the American University

Students Hate Them. Universities Need Them. The Only Real Solution to the A.I Cheating Crisis

The Typical College Student Is Not Who You Think

“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 Transformative Leadership Conversations, I sit down with Amy Shilliday, a learning experience designer, neurodiversity advocate, and founder of Shilliday Vaughan Consulting. With over 25 years in corporate learning and development, Amy has seen firsthand how small shifts in the way we design learning and lead teams can completely change the game - not just for those with ADHD or other neurodivergent profiles, but for everyone.

You’ll hear us discuss:

• Why ADHD and other neurodivergent traits are less about deficits and more about different operating systems
• How “universal design for learning” can transform training and onboarding for every employee, not just some
• Practical ways leaders can coach team members with ADHD without micromanaging or labeling
• The power of disclosure - when, how, and why someone might choose to share their diagnosis at work or in an interview
• What leaders with ADHD themselves can do to embrace their strengths, manage their energy, and lead authentically
• Why self-care isn’t optional and how burnout shows up differently for neurodivergent professionals

Resources

Amy Shilliday on the Web | LinkedIn

The UDL Guidelines

Edge Foundation (Sir Richard Branson)

Feel Good Productivity (Ali Abdaal) - An excellent way for anyone, especially ND folks, to set realistic goals

When All Minds Thrive (Saskia Schepers) - Helps leaders realize the benefits of and support methods for ND employees

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

"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 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 live

Resources

Stephanie Scheller on LinkedIn | Grow Disrupt

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]

"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 it shows up in the workplace, and why understanding it matters for every leader - whether you have ADHD yourself, work with someone who does, or just want to create a team culture where different kinds of brains can thrive. I’ll also share a fictional but very real-to-life story of “Martina,” a leader whose career shifted the moment she stopped forcing herself to work against her brain and learned how to work with it.

You’ll hear me discuss:

• What ADHD actually is (and isn’t), including how it affects brain chemistry and structure
• Why ADHD looks different in adults - especially in women - and why it’s often underdiagnosed
• The challenges ADHD can bring at work, from time blindness to emotional swings
• Surprising strengths many people with ADHD have, including creativity, adaptability, and hyperfocus
• Practical strategies to make work more ADHD-friendly, like body doubling, time blocking, and simplifying decisions
• How environment, support, and self-awareness can turn ADHD traits into leadership assets
• The fictional story of Martina, a leader who transformed her performance by building systems around her brain instead of trying to change it
• Why honoring how your mind works - and the minds of others - can make you a more effective and inclusive leader

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

Articles Referenced

Understanding ADHD

Attention-Deficit/Hyperactivity Disorder (ADHD)

6 strengths and benefits of ADHD

ADHD in Adults: An Overview

24 ADHD Statistics for 2024

The Executive’s Guide to ADHD: Tools for Enhanced Focus and Decision-Making in the Corporate World

Leading with ADHD: A Practical Blueprint for Sustainable Success

The Adult Hyperfocus and Motivation Scale: A Pilot Study

https://totallyadd.com/wp-content/uploads/White_Shah_ADHDCreativity_PAID.pdf?utm_source=chatgpt.com

Uninhibited imaginations: Creativity in adults with Attention-Deficit/Hyperactivity Disorder

Hyperfocus: The Forgotten Frontier of Attention

Living "in the zone": hyperfocus in adult ADHD

What Are the Benefits of Having ADHD?

The unique contribution of emotional impulsiveness to impairment in major life activities in hyperactive children as adults

Understanding Hypersensitivity in ADHD

"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 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 ever

Resources

Neri Karra Sillaman on Website | LinkedIn | Neri's book: Pioneers: 8 Principles of Business Longevity from Immigrant Entrepreneurs

Winnie da Silva on LinkedIn | On the Web | Substack | Email - [email protected]

"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, 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 leadership

Resources

Arjita Sethi on New Founder School | Arjitha's Advantage Program | LinkedIn