Explore every episode of the podcast Transformative Leadership Conversations with Winnie da Silva

Are you really owning your job, or just getting through it? In this episode, I’m thinking about what it actually means to take ownership of your work when you’re not the owner. I’m talking about accountability, curiosity, emotional intelligence, resilience - and how those qualities can help me move through the barriers, complexity, and frustration that come with work.

Resources

Want to Set Yourself Apart? Own Your Job

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Welcome to Season Seven!

Do you like tiny experiments? That's what's happening this season on Transformative Leadership Conversations.

Winnie da Silva is going to be sharing short weekly episodes called Winnie Unscripted tackling all things leadership, from what's in the news, to new insights and ideas from client work to questions for experts and leaders in the community. There will also be a monthly full-length interview with a leading expert sharing their thoughts and experiences.

Want to get involved? Reach out to Winnie da Silva with your questions, challenges, insights and ideas.

“The moments that stretch us most as leaders often become the moments that transform us most — if we are willing to engage them intentionally.” - Winne da Silva

Growth sounds inspiring until it asks you to let go of the habits, mindsets, and approaches that got you where you are today. So what happens when your greatest strengths start becoming your biggest limitations? And how do you continue evolving as a leader in a world that's changing faster than ever before?

In this final episode of Season 6, I'm reflecting on the biggest lessons from our Think Differently, Transform How You Lead series. I revisit the leadership myths we've challenged, the frameworks we've explored, and the reality that meaningful transformation is rarely quick, easy, or comfortable.

You'll hear me discuss:

• Why transformation often begins when the approaches that once made us successful stop working
• How complexity, uncertainty, and rapid change are reshaping what leadership requires from us
• Why avoiding conflict can quietly undermine trust, innovation, and team effectiveness
• The leadership qualities that become even more valuable as AI continues to evolve
• Why strategic thinking, judgment, communication, empathy, and influence remain deeply human advantages
• How growth happens through experimentation, reflection, practice, and challenge
• The role trusted partners, coaches, and advisors can play in accelerating transformation

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

"Transformation of any kind is rarely one insight, one coaching session, one workshop, or one conversation.” - Winnie da Silva

Leadership challenges are rarely just about what’s happening on the surface. The issue that keeps resurfacing, the team dynamic that won’t improve, or the frustration you can’t seem to solve may actually be driven by something much deeper.

In this episode, I share three real client stories from my executive coaching, leadership development, and team effectiveness work to show how lasting transformation happens when we uncover the stories, assumptions, leadership habits, and trust dynamics shaping our behavior and results.

You'll hear me discuss:

• How the stories we tell ourselves influence the way we lead and the results we create
• Why one leader's hidden assumptions were keeping him stuck and preventing real progress
• How adaptive leadership helps us choose the right approach for the right person and situation
• What causes leaders to unintentionally overuse their preferred leadership style
• Why communicating your leadership intent can strengthen trust and improve team performance
• How trust grows when people move beyond assumptions and gain a deeper understanding of one another
• The common thread connecting leadership challenges across individuals, teams, and organizations

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Trust doesn’t just magically happen or appear. It’s built through deliberate action and honest conversations.” - Winnie da Silva

Trust impacts everything at work - communication, collaboration, influence, decision-making, and team culture. But most leaders still treat it like something that naturally develops over time instead of something that needs real intention and strategy. In this episode, I’m unpacking how trust actually gets built, why it breaks down so easily, and the practical frameworks I use with leadership teams to strengthen the relationships that matter most.

You’ll hear me discuss:

• Why broken trust quietly drains energy, productivity, and team effectiveness
• The four core components of trust: knowing the person, competence, sincerity, and reliability
• Why people approach trust completely differently and how misunderstanding that creates friction
• Practical ways to intentionally strengthen trust through better conversations and clearer expectations
• Why senior leaders must learn to build trust horizontally across the organization, not just within their teams
• How understanding someone’s motivations, values, and “currency” improves influence and collaboration
• The stakeholder analysis tool I use to help leaders build stronger, more strategic work relationships

Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Adaptive leadership is about choosing the right leadership approach for the right people in the right situation.” - Winnie da Silva

Some leaders hold on too tightly. Others delegate too fast. In this episode, I break down the adaptive leadership framework I’ve used for years with everyone from first-time managers to CEOs, and explain why effective leadership is rarely about sticking to one style.

I walk through the continuum of directing, collaborating, and delegating, and share how I decide which approach fits the person, the situation, and the moment.

You’ll hear me discuss:

• Why adaptive leadership is about choosing the right leadership approach for the right person and situation
• How the leadership continuum shifts between directing, collaborating, and delegating
• The three things I evaluate before deciding how to lead someone
• How trust, risk tolerance, and leadership instincts shape leadership decisions
• Why clarity and direction can slowly turn into micromanagement
• How collaboration and delegation build ownership, growth, and stronger decision-making
• Why great leaders constantly reassess and adapt instead of relying on one leadership style

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“If we want better results, we have to examine the stories and assumptions driving our behavior.” - Winnie da Silva

Some leadership challenges don’t start with strategy or communication, but rather they start with the stories we’re telling ourselves. The assumptions running quietly in the background about who I am, who other people are, and how things work.

In this episode, I explore how those internal narratives shape our behavior, influence our leadership, and ultimately impact the results we get. I also break down how changing the story can lead to completely different outcomes.

You’ll hear me discuss:

• How the stories we tell ourselves shape our behavior and results
• The three types of stories that influence leadership decisions every day
• Why certain problems keep repeating until we challenge the assumptions underneath them
• How stories about other people affect trust, collaboration, and conflict
• The importance of catching ourselves in the moment and questioning our assumptions
• Why curiosity is far more productive than self-judgment when trying to grow as a leader
• How adopting a new story can create better behaviors and better outcomes

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“When you can show up in service of someone else’s work ahead of your own, it stops feeling transactional.” - Carly Valancy

Networking has become one of the most dreaded words in professional life. It feels transactional, awkward, and exhausting. But in a world increasingly driven by AI and digital communication, real human connection may be more valuable than ever.

In this episode, I sit down with Carly Valancy, founder of Reach Out Party, to talk about her philosophy of “anti-networking” - a more human, generous, and courageous way to build relationships and create opportunity.

You’ll hear us discuss:

• Why traditional networking feels so uncomfortable and how to approach it differently
• Carly’s framework for writing “unignorable” messages that people actually respond to
• The hidden fears that stop most people from reaching out in the first place
• Why reaching out is one of the highest leverage things you can do for your career
• How planting seeds for your future self can create opportunities years later
• The unexpected internal confidence shift that happens when you consistently put yourself out there
• Why meaningful human connection is becoming a major differentiator in an AI-driven world

Resources

Carly Valancy on Website | Reach Out Party | Tether | Substack | LinkedIn | Momentum Growth Plan

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Leadership growth happens when we begin practicing new behaviors in the real world.” - Winnie da Silva

Some of the biggest leadership breakthroughs don’t come from massive reinventions. They come from one small shift repeated consistently over time.

In this episode, I’m digging into why so many leaders get stuck thinking about growth instead of actually practicing it and why tiny experiments might be one of the most powerful tools for real leadership development.

You’ll hear me discuss:

• Why leaders often get trapped thinking about growth instead of practicing new behaviors
• How tiny experiments reduce overwhelm and make meaningful change feel more achievable
• Why confidence is usually built through action and repetition, not before it
• The power of small, consistent leadership behaviors over dramatic transformation
• How reflection frameworks like “plus, minus, next” help create sustainable growth
• What I learned from running my own public leadership experiment around strategic thinking
• Why experimentation, adaptability, and continuous learning are becoming essential leadership skills today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Tiny Experiments in Leadership Thinking episode - December 2025

“Leadership at scale isn’t about having all the answers—it’s about drawing out other people’s thinking.” - Winnie da Silva

Why do so many leaders feel like they have to carry all the answers, and what is it actually costing them?

In this episode, I unpack one of the most overlooked leadership tools: asking better questions. I share why constantly jumping in with solutions can quietly limit your team’s thinking, and how shifting toward thoughtful, open-ended questions can completely change the way you lead. It doesn’t mean stepping back or losing authority, but it does elevate the quality of conversations, decisions, and ownership across your team.

You’ll hear me discuss:

• Why having all the answers can actually hold your team back
• How asking questions creates ownership instead of dependency
• The connection between inquiry and reducing defensiveness
• How better questions uncover hidden risks, assumptions, and blind spots
• Why leaders who ask more questions tend to make stronger decisions
• How questions build trust and increase accountability across teams
• Simple, real-world questions you can use in conversations starting today

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Example Questions: Understanding someone’s thinking

• “That’s an interesting point. Tell me more about what you're thinking.”
• “When you say X, what does that mean to you?”
• “What would need to be true for this to work?”
• “What do you care most about in this situation?”

Collaboration and partnership

• “How might we best partner together on this?”
• “What role would you like me to play here?”
• “What decision do you need from me today?”

Feedback conversations

• “What feedback do you have for me?”
• “What’s hard to tell me?”
• “What are we not talking about that we probably should be?”

Vision and goals

• “If you and your team could only achieve one thing this year, what would it be?”
• “What challenge, if solved, would make the biggest difference?”
• “What are your top priorities and why?”

Problem-solving and decision-making

• “What might be the root issue underneath this?”
• “What are we implicitly saying no to by saying yes?”
• “What data would change your mind?”

“The issue isn’t the strength of the idea. It’s whether it connects to what the other person cares about.” - Winnie da Silva

Why do some ideas land instantly… while others just hang in the air, no matter how well you explain them?

In this episode, I break down a simple but powerful leadership concept that can completely change how you influence others, especially when you don’t have formal authority. I share how understanding what people truly care about (their “currency”) can shift conversations, build trust faster, and help your message actually stick.

You’ll hear me discuss:

• Why strong arguments alone don’t guarantee influence
• What “currency” really means and how it shows up in everyday leadership
• How to spot what someone values based on their behavior and priorities
• Simple ways to reframe your message so it connects and lands
• How this applies to stakeholders, feedback, trust-building, and big conversations
• Why influence is less about pushing your point and more about aligning with what matters to others

Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“The goal isn’t ideas—it’s behavior change that drives business results.” - Winnie da Silva

Why do so many leadership programs fall flat even when the content is solid? I’ve seen this play out time and time again over the past two decades. It’s rarely about the quality of the program itself. It’s about what’s happening around it. In this episode, I break down the two factors that actually determine whether leadership development creates real, lasting change. I also share where things tend to go wrong.

You’ll hear me discuss:

• Why leadership development only works when both the leader and the organization are fully engaged
• The mindset shifts I consistently see in leaders who grow the fastest
• What it really looks like to apply leadership development in real time (not just learn it)
• How organizational culture and senior leadership behavior can make or break development efforts
• Why treating leadership development as a “check-the-box” exercise leads to poor results
• What needs to be in place for leadership growth to actually stick and drive business outcomes

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“In leadership, the visible problem is often just the symptom.” - Winnie da Silva

Is the problem you’re trying to solve actually the real problem or just the most obvious one?

In this episode, I unpack why so many leadership challenges don’t get resolved the way we expect, and how quickly jumping to solutions can keep us stuck in the same cycles. I share a real client story and walk through how to slow down just enough to uncover what’s really driving the issue, so you can create solutions that actually last.

You’ll hear me discuss:

• Why the visible problem is often just a symptom, not the root cause
• How pressure and urgency push us into solving the wrong thing
• The difference between surface issues and deeper organizational dynamics
• A real example of how misalignment at the top created slow decision-making
• The role of trust, expectations, and avoided conversations in team challenges
• Simple questions I use to dig deeper and challenge my own assumptions
• How pausing, gathering input, and testing solutions leads to better outcomes

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Coaching isn’t remediation. It’s acceleration.” - Winnie da Silva

Is executive coaching really just a last resort for struggling leaders… or is that completely missing the point? In this episode, I unpack one of the biggest myths around coaching and share what I actually see in my work with high-performing leaders. I explain why leadership coaching is about growth, not fixing, and why the right support at the right time can completely shift your leadership impact.

You’ll hear me discuss:

• Why coaching is often misunderstood as a performance fix instead of a growth accelerator
• What really changes when a strong leader steps into a bigger, more complex role
• How blind spots show up even for high performers and how I help uncover them
• Why reflection is something most leaders don’t get enough of (and why it matters)
• How coaching creates space to think differently, test ideas, and navigate complexity
• The difference between coaching and other tools like feedback, training, or performance management
• A real example of how one leader expanded their impact by shifting how they influence and make decisions

Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Real leadership work isn’t about fixing people—it’s about addressing root issues.” - Winnie da Silva

Are you stepping into bigger leadership… but still thinking and operating the same way?

In this episode, I break down what it really takes to grow as a leader when the pressure, complexity, and expectations all level up. I share how I work with leaders and teams, the frameworks behind that work, and why lasting change comes from mindset shifts instead of quick fixes.

You’ll hear me discuss:

• Who I work with and the types of leadership transitions and challenges they face
• Why leadership is less about industry and more about mindset and people
• What executive coaching actually looks like and how it drives real results
• Why leadership development must lead to behavior change, not just learning
• The three core areas of my work: coaching, leadership development, and team effectiveness
• How to tell if a team is truly effective (and what to look for)
• Why sustainable results come from addressing root causes, not quick fixes

Resources

Celebrating 20 Years of Transformative Leadership Episode

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“Most leadership problems aren’t what they seem.” - Winnie da Silva

You might think the issue in front of you is the real problem… but what if it’s just the surface? This season, I’m shifting things a bit. Instead of longer guest conversations, I’m bringing you shorter, more focused episodes designed to help you think more clearly, challenge your assumptions, and take immediate action in your leadership. Because the truth is, most leadership challenges aren’t as straightforward as they seem, and if we don’t slow down and look deeper, we risk solving the wrong problem entirely.

In this episode, I’m setting the stage for what’s ahead and sharing why this shift matters, especially if you’re navigating complex, messy, real-world leadership situations.

You’ll hear me discuss:

• Why many leadership problems are often misdiagnosed at first glance
• What tends to sit beneath common challenges like performance issues or communication breakdowns
• How unexamined assumptions and internal narratives can quietly shape your leadership effectiveness
• Why solving only what’s visible can lead you to miss the bigger issue
• The idea that leadership isn’t about fixing people, but about addressing root causes
• How asking better questions can become your most powerful leadership tool
• What it looks like to adapt your leadership approach based on people and context
• The frameworks I use with clients to build trust, experiment, and lead more intentionally
• How this season is designed to give you practical, usable insights you can apply right away

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

Today's episode includes a discussion of child sex trafficking and sexual exploitation. While our goal is awareness and prevention, some listeners may find this topic difficult. Please take care of yourself and feel free to pause or skip this episode if needed.

“Rescuing one girl matters - because that one life can change the future of an entire family.” - Leah Henck

How does trafficking continue to thrive in plain sight - even in places with laws designed to stop it?

In this special episode, I sit down with Leah Henck, President of Freedom Firm USA, to talk about the reality of child sex trafficking in India and the long, persistent work required to fight it. Freedom Firm partners with law enforcement, the courts, and social workers to rescue girls, support their healing, and pursue justice against those responsible.

Leah shares powerful stories from the field and explains why real change requires more than rescue. It also requires addressing the systems that allow exploitation to continue.

You’ll hear us discuss:

• How Freedom Firm began and why its mission focuses on rescue, restoration, and justice
• Why rescuing girls alone isn’t enough without changing the systems that allow trafficking to continue
• How traffickers often move girls across regions or countries to isolate and control them
• What it takes to work with police and the judicial system in places where trafficking has been normalized for decades
• The emotional and practical challenges girls face after being rescued
• Why every survivor’s path to healing looks different
• How convictions against traffickers can slowly change an entire region
• The role vulnerability plays in trafficking everywhere, including in the United States
• Why community awareness and support are critical in preventing exploitation
• How one rescued girl can break a cycle that may have existed in her family for generations

Resources

Leah Henck on Freedom Firm | Freedom Firm Facebook | Freedom Firm Instagram | Sign up for Monthly Impact Update Email | Email: leah@freedomfirm.org

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 possible

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 conditions

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 Stopper

Confidence 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 time

Resources

Angela Stopper on LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 Silverman

Confidence 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 confidence

Resources

Julienne H. Silverman on LinkedIn | On the Web

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“We are not meant to force ourselves into monochromatic, one-tone grinds that look and feel the same every single day.” - Winnie da Silva

High-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 leadership

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - 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
• Impact of microbiome composition on social decision making
• The connection between stress and empathy
• Link between empathy and inflammation

Special Offer for Listeners

Jan-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.

It’s a four-month journey that begins with a comprehensive at-home diagnostic — including stress-hormone and cortisol analysis, ECG monitoring, and recovery analytics — followed by three months of expert-guided habit coaching and monthly progress tracking.

Whether stress has already started to take a toll — on your body, your work, or your relationships — or you’re simply curious about how your body responds under pressure, this program can help you understand what’s happening beneath the surface and make small, data-informed changes that build lasting performance and wellbeing.

If you’d like to learn more or see if this program is right for you, you can book a free 15-minute discovery call with a member of the Sapiens team using this link:

???? Book a Consultation

When you sign up, use the podcast code - TLC — and visit www.be-sapiens.com for full details.

"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 complex decision making.” - Jan-Philipp Martini

“If you can get more insight into what drives you, you can handle yourself — and your leadership — much better.” – Martin Redigolo

Stress has a funny way of showing up long before we notice it - our bodies feel it first, and our calendars catch up later.

In this episode, I bring Martin Redigolo and Sapiens founder Jan-Philipp Martini together so we can connect the dots between the science, the story, and the real human experience of leading under pressure. Martin actually went through the full Sapiens Stress & Resilience Diagnostic, and he shares what the process was like, what surprised him, and how the results shifted the way he understands himself as a leader.

And because Jan-Philipp is with us too, we dig into the “why” behind the data - how stress shows up in the body, what most leaders overlook, and how small, realistic habit shifts can make a huge difference in how you feel and how you perform.

This conversation pulls the whole series together in a way that’s super grounded, practical, and honestly… eye-opening.

You’ll hear me discuss:

• How Martin’s diagnostic unfolded and the parts of the process that were surprisingly simple (and surprisingly revealing)
• The moments when the data challenged what he thought he knew about his own stress
• How the ECG and cortisol analysis make invisible stress completely visible
• The three core questions the Sapiens report answers for every leader
• The subtle patterns in your day that can drive fatigue or restlessness without you realizing it
• Why it matters to work with your biology before trying to change your mindset
• How chronic stress quietly undermines things like empathy, creativity, and decision-making
• The shifts Martin is making now - at work and at home - because of what he learned
• a few habit changes that are simple, doable, and grounded in real science
• what sustainable leadership actually looks like when you’re aiming for excellence without exhaustion

Resources

Jan Philipp Martini on Sapiens | LinkedIn

Martin Redigolo on Web | LinkedIn

Book a 15-minute free demo consultation - Link

Research: How We Measure Stress Using Body Data and Self-Assessments: Read here

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - 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
• Impact of microbiome composition on social decision making
• The connection between stress and empathy
• Link between empathy and inflammation

Special Offer for Listeners

Jan-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.

“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 Martini

Have 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 exhaustion

Resources

JanPhilipp Martini on Sapiens | LinkedIn

Book a 15-minute free demo consultation - Link

Research: How We Measure Stress Using Body Data and Self-Assessments: Read here

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

• Impact of microbiome composition on social decision making

• The connection between stress and empathy

• Link between empathy and inflammation

Special Offer for Listeners: Jan-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 by using the code TLC at www.be-sapiens.com, valid through the end of 2025.

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“The stress I carried slowed me down — I couldn’t think clearly, and I didn’t recognize myself anymore.” - Martin Redigolo

What 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 pressure

Resources

Martin Redigolo on Web | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - 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, with the offer valid through the end of 2025.

“People do change - sometimes by choice, sometimes by necessity, but always through connection.” - Winnie da Silva

Can 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.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 Silva

Is 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 practice

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

“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 - winnie@winnifred.org

‘’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 - winnie@winnifred.org

“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 - winnie@winnifred.org

“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 - winnie@winnifred.org

“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 - winnie@winnifred.org

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 - winnie@winnifred.org

"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 - winnie@winnifred.org

"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 - winnie@winnifred.org

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 - winnie@winnifred.org

"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

“There is a knowing in me that beneath that cultural layer, we’re the same. It sounds so obvious, but it has made me show up in different ways.”  - Anna Gudmundson

What does it really take to lead with purpose when you’re building a life - and a business - in a country that’s not your own?

In this episode, I sit down with Anna Gudmundson, CEO of Sensate and a global tech entrepreneur whose story 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 leaders

Resources

Anna Gudmundson on Sensate | Sensate Instagram | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

“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 leaders

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

“Leadership isn’t about being perfect or popular. It’s about making decisions, taking responsibility, and developing the skills that allow us to show up with courage and confidence.” - Lorraine Connell

Are we unknowingly holding kids back by tying leadership to titles, popularity, and perfection? Could our entire approach to teaching leadership be setting young people up to fail before they even 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 everyone

Resources

Lorraine Connell on Peers not Fears | ''Leadership for Our Kids!'' Facebook Group | Lorraine's books on Teenage Leadership I LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"All leaders should be leading with kindness and empathy and respect for other people, which in general, I think means by leading with example." - Aradhna da Silva



Could the clearest vision for future leadership come not from boardrooms, but from high school classrooms?

In this episode, I flip the mic and turn to the next generation. After speaking at my daughter’s high school career day, I 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 leaders

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

“If we’re serious about developing the next generation of leaders, we have to be just as serious about questioning the models we’re handing down.”- Winnie da Silva

Is Gen Z quietly rewriting the rules of leadership - and are we even paying attention? Seventy-two percent (72%) of Gen Z would prefer a non-managerial path to career advancement. They see leadership roles as too high stress and low 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 like

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"I think we overestimate the importance of knowing and underestimate the power of listening." - James Misner

What if the biggest thing holding back real change is the way we try to create it? In this conversation of Transformative Leadership Conversations, I speak with James Misner — a leader, storyteller, and deep thinker who challenges how we show up for others, especially those on the margins. 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.

Resources

James Misner on The Kipos Group | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

‘’Even in a non-profit context, issues of sharing power and mutual respect and dignity are essential and not universal.” - Rebecca Vander Meulen

What does it take to lead with courage, clarity, and compassion when the systems around you collapse—almost overnight? In this episode of Transformative Leadership Conversations, I speak with Rebecca Vander Meulen, Executive Director of the J.C. Flowers 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.

Resources

Rebecca Vander Meulen on LinkedIn | J.C.Flowers Foundation

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"The need for leaders who fund, champion, and drive social causes has only intensified — we need them now more than ever." - Winnie da Silva

What if the most powerful leadership lessons aren’t coming from boardrooms—but from leaders fighting for dignity, justice, and community impact? In this episode of Transformative Leadership Conversations, I explore stepping beyond the walls of traditional leadership and into the world where return isn’t measured in revenue, but in real human impact. As someone who started my career in social work, this theme is personal. And now, with global funding shifts and social issues intensifying, learning from those who lead with purpose at the core feels more urgent than ever.

You’ll hear me reflect on the values, challenges, and mindset of social impact leadership and how these insights can shape leadership at any level—whether you're scaling a non-profit, launching a start-up, or leading a legacy business.

You’ll hear me discuss:

• The urgency of now: Why 2025 may be the hardest—and most vital—year yet for leading social change.
• Purpose over profit: What business leaders can gain from those who lead with mission at the centre.
• Leadership mindset shifts: Seven powerful lessons from the non-profit world that apply across every sector.
• Fundraising reframed: How telling your story and aligning others with your mission can fuel—not distract from—your work.
• Small scale, big impact: How one relationship-based programme quietly sparked new movements across the U.S.
• Innovation under constraint: Why limited resources often unlock the most creative, adaptive solutions.
• Leading through uncertainty: The importance of communicating—even when you don’t have all the answers—and staying grounded in your values.
• Upcoming guests: A preview of insights from Rebecca Vander Meulen and James Misner, two leaders who embody resilience and purpose in action.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"You combine the gender wage gap with the work breaks, what you get is a retirement account that has less money in it at the point of retirement. And then we outlive men.” - Jean Chatzky

What if the way you feel about money is more powerful than what you actually know about it? Managing money is not about being perfect — but just about building the right habits, over and over again. In this episode of Transformative Leadership Conversations, I’m joined by Jean Chatzky — financial journalist, bestselling author, and CEO of HerMoney. Jean has spent her career helping people, especially women, take control of their money, their mindset, and their future. We dive deep into how your personal money story shapes your confidence, your career moves, and even your leadership style — and why good money management has way more to do with habits than with being "perfect" at finance.

You'll hear us discuss:

• Building Habits, Not Perfection: Why getting better with money isn’t about knowing everything — it’s about doing the small smart things over and over again.
• Why Women Need a Different Space: How Jean created HerMoney as a judgement-free zone where women can learn, talk, and build financial strength together.
• The Hidden Cost of the Wage Gap: How career breaks, lower salaries, and longer lifespans are stacking the odds against women — and what we can do about it.
• Money Stories: Why the way you watched your parents handle money matters more than what they ever taught you out loud.
• Making the Shift from Money to Value: How thinking about your value — not just your salary — can totally change how you negotiate and lead.
• Letting Go of Perfect: Why waiting until you’re 100% sure can hold you back — and why “good enough” is often exactly what you need to move forward.
• Behavioural Tricks That Work: How little psychology hacks like automation and visualisation can make saving, investing, and budgeting easier without even thinking about it.
• Keeping Your Receipts (Literally and Figuratively): Why you should start a “value file” today — and how it can make all the difference when you’re asking for a raise or a promotion.
• Knowing When to Get Help: Why even Jean has a financial advisor — and why getting help is a smart leadership move, not a sign you’re failing.

Resources:

Jean Chatzky on Her Money (Web) | Money Personality Type Test | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"You cannot negotiate against yourself. Ask questions, gather data, be prepared—but don’t assume the answer before you even start the conversation." - Gini Dietrich

What if the thing holding you back from making more money… is you? In this episode of Transformative Leadership Conversations, I’m chatting with Gini Dietrich, a seasoned PR pro and the founder of Spinsucks. Gini’s not just a business owner, she’s someone who’s learned the hard way about money, confidence, and leadership.

From a tough start to building an incredible business, Gini’s story is a testament to what happens when you get real about your value—and how so many of us (especially women) hold ourselves back from truly owning it. If you’ve ever second-guessed your pricing, been nervous to ask for a raise, or just don’t know how to explain your value to others—this episode is for you.

You’ll hear us discuss:

• It’s not just numbers, it’s mindset: A big part of negotiation skills is about your confidence—and often, fear. Gini talks about why it’s important to learn how to overcome this, to get paid what you are worth.
• It’s not just numbers and mindset, it’s also about the right formula: Pricing isn’t some mysterious or random guess—it’s about knowing your costs and the profit you want to make. Gini explains how the correct price is actually calculated by factoring in your expenses plus the profit you aim for, and why you need to treat your rates as an evolving process, not a static figure.
• Confidence is a muscle: Whether you’re running your own business or climbing the corporate ladder, confidence isn’t automatic. Gini shares how building financial confidence is something you have to work at, constantly.
• Stop negotiating against yourself: So many of us do this without realizing it! Gini talks about the hidden ways we sabotage ourselves before we even sit down for that important conversation with a boss or client—and how to stop that cycle.
• Keep it professional: When you’re asking for more—whether it's a raise or a new project—don’t bring in personal stuff like credit card debt. Gini’s advice? Stick to the value you bring to the table, not what you need to solve personal problems.
• Focus on the value, not the ‘deserve’ factor: We often approach negotiations by asking, “Why do I deserve this?” Gini flips the script and explains why it’s all about showing your boss, your clients, or even yourself, how much value you’re adding.
• Data, data, data: You need to be armed with the facts when it comes to negotiating. Gini shares why doing your research and having the numbers to back up your requests is so critical to making your case.
• This isn’t just for business owners: Even if you don’t run your own company, this conversation is packed with practical advice for anyone looking to take charge of their career and negotiate for what they’re worth.

Resources

Gini Dietrich on Spin Sucks | LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

What if the reason you're not earning what you're worth has nothing to do with your skills — and everything to do with the stories you believe about money? Are you showing up like someone who knows their value… or playing it small to keep the peace? Let’s be real — money is messy. It brings up all kinds of emotions, expectations, and unspoken rules. In this solo episode, I’m sharing something personal: my own journey around money, self-worth, and what it’s taken for me to finally feel comfortable asking for what I deserve.

This episode kicks off a new theme we’re exploring this month: Leadership & Money Mindset. If you’ve ever hesitated to ask for a raise, felt weird quoting your rates, or second-guessed your worth, this one’s for you. I’m talking through the mindset shifts I had to make (and am still making!) to move from discomfort and doubt to clarity and confidence — and how you can do the same.

You’ll hear me discuss:

• What happens when you don’t value yourself. I used to feel weird asking to be paid — like it somehow made me less sincere. But I’ve learned that when I don’t own my value, other people don’t either. That had to change.
• The early money messages that shaped me. I grew up in the Midwest, where the rule was: don’t make anyone uncomfortable — especially with money talk. That silence stuck with me for years. Maybe you can relate?
• A simple framework that helps uncover limiting beliefs. I share the Story → Behavior → Result model I use with clients to break down what's really driving your actions — and how to shift it.
• Three powerful client stories — Annie, Eleanor, and Zoe. These are women who faced real turning points in their careers — promotions, negotiations, job changes — and had to totally reframe how they saw their own value. Their courage might give you the nudge you need.
• The bigger forces that make this harder, especially for women. We’ll touch on why this issue isn’t just personal — it’s also systemic. From unpaid labor to leadership stereotypes, there’s a lot working under the surface.
• A surprisingly fun tool to explore your money mindset. I’ll introduce you to the Money Type Personality Assessment (yep, it’s free!) and share what I learned about myself as a “Visionary” with a close second of “Nurturer.”
• Five big takeaways to help you shift your mindset now. These are practical, real-world ideas you can apply — whether you're pricing a project, negotiating a role, or simply trying to stop shrinking yourself at work.

Resources

Money Type Personality Test

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

“No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal

Is your pitch holding you back more than your business idea? Are you making it easy for investors to dream the dream with you? In this episode, I sit down with Medha Agarwal, General Partner at Defy, to talk about the unique challenges founders face—especially women—when pitching their startups, securing funding, and leading through growth. She shares why too many founders unknowingly undersell their vision and how simple shifts in storytelling can make all the difference.

Medha also opens up about her own career journey, from being a founder to working in venture capital, and what she’s learned about choosing the right team, adapting in fast-moving startups, and pushing past perceived limits. We also dive into her experience as a Harvard rower and the powerful leadership lessons she’s carried from the water to the boardroom.

Whether you're a founder, thinking about launching a startup, or simply curious about what separates the best pitches from the rest, this conversation is packed with actionable insights on confidence, resilience, and strategic growth.

You'll hear us discuss:

• Why women founders struggle with selling the big picture – Medha explains that many female founders naturally emphasize what still needs to be done rather than what they’ve already achieved. Investors need to see the vision and the opportunity, not just the challenges ahead.
• The subtle shift that makes a pitch stronger – Instead of pointing out gaps or weaknesses, founders should frame their journey as momentum. Investors want to be inspired—help them see how they can be part of something big and inevitable.
• The underestimated importance of flexibility in startups – Too often, people transitioning from corporate jobs to startups focus on titles and initial responsibilities. But in a fast-growing company, your job will change drastically every six months. The real key to success is choosing the right company and founder rather than clinging to a specific role.
• What makes a startup worth joining – Medha stresses that it's better to join a company where you believe in the founder’s vision and leadership style, even if the role isn’t perfect. A rising tide lifts all boats—if the company succeeds, so will your career.
• How rowing taught her to lead and collaborate – Rowing is the ultimate team sport, where trying to stand out individually slows the whole boat down. The same applies in startups—success comes from alignment, trust, and moving in sync with the team.
• The reason she prefers working behind the scenes – Medha admits she’s uncomfortable with the spotlight on herself and much prefers helping others shine. This mindset makes her a stronger investor and advisor—she’s fully focused on helping founders succeed, not chasing personal recognition.

Resources

Medha Agarwal on LinkedIn | Defy

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

"My role is catching the ideas and making them happen." – Stephanie Unwin

Is your leadership moving forward, or are you just keeping busy?

In the fast-paced world of executive leadership and entrepreneurship, it can feel impossible to carve out time to think strategically. But what if making space for reflection isn’t a luxury—it’s the key to unlocking long-term success? In this episode of Transformative Leadership Conversations, I sit down with Stephanie Unwin, a seasoned executive and business leader, to explore how prioritizing strategic thinking not only makes you a stronger leader, but also helps you steer your company toward sustainable growth.

Stephanie opens up about the importance of deliberately carving out time for reflection, recharge, and deep thinking—ensuring that leadership isn't just about constant action but also about intentional decision-making that shapes the future of the business.

You'll hear us discuss:

• Why carving out time to think is not a “nice to have”—it’s a leadership necessity. As an executive, it’s easy to get swept up in the whirlwind of daily demands—meetings, emails, and urgent decisions that take up most of your day. However, without setting aside dedicated time to reflect, refine strategy, and gather your thoughts, leaders risk losing sight of the bigger picture.
• The secret to balancing high-energy execution with moments of clarity. Leading a company often feels like an unending sprint. While constant action and execution are important, Stephanie explains how never taking a step back to pause and think can lead to burnout, decision fatigue, and reactive leadership.
• Why founders and executives must stay aligned on vision, values, and risk-taking. Whether you’re working for a founder or running a startup yourself, one of the most critical components of leadership is alignment. Stephanie dives deep into why executives must ensure that their vision, values, and approach to risk-taking are in sync with the founders or leadership team.
• How to navigate change without losing sight of the bigger picture. The business world is in a constant state of flux—markets shift, technologies evolve, and customer demands change. Leaders who resist change or get bogged down by every shift risk falling behind. Stephanie shares her approach to staying agile, adapting to changes, and continuously innovating without compromising the company's core mission and values. .
• The underestimated power of trusting your team and leveraging their insights. No leader has all the answers, and the most effective leaders are those who recognize the importance of collective intelligence. Stephanie highlights how fostering a culture where team members feel empowered to share ideas, challenge assumptions, and contribute to strategic discussions can greatly enhance decision-making.

Resources

Stephanie Unwin on LinkedIn

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org