Transformative Leadership Conversations with Winnie da Silva

“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 - [email protected]

“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 - [email protected]

“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 - [email protected]

"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 - [email protected]

“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 - [email protected]

"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 - [email protected]

‘’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 - [email protected]

"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 - [email protected]

"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 - [email protected]

"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 - [email protected]