“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

“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