Transformative Leadership Conversations with Winnie da Silva

“Leadership growth doesn’t have to come from huge reinventions. Often, it comes from tiny experiments.”

Busyness has a sneaky way of convincing us that it equals importance - and for a long time, I let that idea drive how I measured my value as a leader. In this bonus episode, I’m sharing what happened when I decided to interrupt that pattern with one small, intentional experiment. No grand strategy. No perfectly mapped plan. Just 45 minutes a week to think - really think - and see what surfaced.

You’ll hear me discuss:

• How I realized I was buying into the belief that my leadership value is tied to productivity
• Why I committed to a short, weekly strategic thinking practice and what I hoped it might change
• How strange and uncomfortable it felt at first to sit with no agenda, no screen, and no clear outcome
• Why even 30 minutes of protected thinking time turned out to be more than enough
• How rest, reflection, and permission played a bigger role than I expected
• What I noticed about my thinking carrying over and deepening between sessions
• Why sticking to pen and paper helped me trust my own thinking instead of outsourcing it
• How one meaningful conversation with a trusted colleague reshaped my strategic clarity
• Why strategic thinking doesn’t have to be a solo activity to be effective
• What consistency, accountability, and keeping the bar low actually made possible

Resources

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

“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 - [email protected]

“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 - [email protected]

“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 - [email protected]

“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 - [email protected]

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 - [email protected]

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 - [email protected]

“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 - [email protected]

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 - [email protected]

“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 - [email protected]