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Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva
Leadership
Sapiens
Executive Coaching
Leadership Development
Higher Education
Stress
Open-Ended Questions
Transformative Leadership Conversations
Tiny Experiments
Neurodiversity
ADHD
Confidence
Unknown
Comparison
Undermining Relationship
Immigrant Entrepreneurship
Anti-Networking
Storytelling
Adaptive Leadership
Chronic Stress

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

PublishesWeeklyEpisodes130Founded6 years ago
Number of ListenersCategories
ManagementBusinessEntrepreneurship

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Artwork for Transformative Leadership Conversations

Latest Episodes

"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 dy... more

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“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... more

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“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 fr... more

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“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... more

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Recent Guests

Carly Valancy
Founder of Reach Out Party and Tether; co-founder of Momentum Growth; writer of A Good Omen
Reach Out Party; Tether; Momentum Growth
Episode: Anti-Networking: How Relationships Create Opportunity with Carly Valancy
Leah Henck
President of Freedom Firm USA
Freedom Firm USA
Episode: Freedom Firm: Rescue, Restoration, Justice with Leah Henck
Dr. Angela Stopper
Chief Learning Officer at UC Berkeley
UC Berkeley
Episode: The Confidence You Learn with Dr. Angela Stopper
Julie Silverman
Partner in the Strategic Advisor Group at PJT Partners
PJT Partners
Episode: The Confidence You Build with Julienne H. Silverman
Martin Redigolo
Executive, discussed his stress journey and Sapiens diagnostic
Sapiens (partner network)
Episode: The Biology Behind Effective Leadership with Martin Redigolo and Jan-Philipp Martini
Jan-Philipp Martini
Founder and CEO of Sapiens, Neurobiologist and stress expert
Sapiens
Episode: The Biology Behind Effective Leadership with Martin Redigolo and Jan-Philipp Martini
Elliot Felix
Author, strategist, designer, entrepreneur and leader in higher education advisory
Borough Happold; Minneapolis College of Art and Design (Board of Trustees)
Episode: Prototyping Better Leadership with Elliot Felix
Dr. Gwendolyn Freed
President of MCAD (Minneapolis College of Art and Design)
Minneapolis College of Art and Design (MCAD)
Episode: Hope and Leadership in Education with Gwendolyn Freed
Gwen Fried
New president of the Minneapolis College of Art and Design; leadership journey through turbulence
Minneapolis College of Art and Design
Episode: Lessons from Higher Education for Every Leader with Winnie da Silva

Host

Winnie da Silva
Host of Transformative Leadership Conversations

Reviews

4.7 out of 5 stars from 22 ratings
  • Inspiring, Insightful and Implementable

    Winnie’s ability to engage her guests in deep, meaningful conversations about leadership is truly remarkable!

    Her Team Development masterclass is both insightful, practical and implementable. The insights shared were not only thought-provoking but also highly applicable to real-world leadership challenges.

    Winnie’s style is both warm and perceptive, making it easy to connect with the content and providing both practical advice and a well-rounded perspective on leadership.

    This podcast is a must-... more

    Apple Podcasts
    5
    RosslynK8
    United Statesa year ago
  • Excellent podcast

    Winnie has great insights and is able to pull meaningful insights from many types of leaders across various industries.

    Apple Podcasts
    5
    ughzxcvbnm
    United States3 years ago
  • Refreshing and Inspiring Insights

    Winnie does a great job boiling down simple basics for her audience.

    Apple Podcasts
    4
    LaurRads
    United States3 years ago
  • Diverse Leadership Approaches

    Diverse approaches to leadership mindset. Leadership approaches from entrepreneurs and other leaders in addressing challenges. Startups, medical, impacts driven by challenges like COVID, all shared in an engaging approach.

    Apple Podcasts
    5
    CR Van
    United States5 years ago
  • Yes!

    I’m so glad Winnie has started a podcast. She is someone I have grown so much from in both my career and personal life, so it’s just awesome to hear more from her and her clients! Can’t wait for more!

    Apple Podcasts
    5
    This app stinks 1234324
    United States6 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

The format balances coaching insights with real-world client stories and case studies.
Listeners praise practical, actionable leadership guidance and warm, engaging interview style.
Strong value for listeners seeking professional development and leadership coaching resources.
Audience finds the leadership frameworks, like tiny experiments and better questions, highly applicable to teams and organizations.
Guests are well-chosen with diverse perspectives across industries and functions.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Prototyping Better Leadership with Elliot Felix
Q: What are some transferable lessons from your work that any leader can apply beyond higher education?
Felix emphasizes cross-boundary collaboration, clear prioritization, and design-thinking mindsets—understanding people first, mapping needs, and prototyping to learn and iterate before committing significant resources.
Making Learning Neurodivergent-Friendly with Amy Shilliday
Q: Could you describe Universal Design for Learning and how it applies to corporate learning?
UDL is about offering multiple representations of content so that different learning preferences are supported, which benefits both neurodivergent and neurotypical learners and doesn't require new software—just reimagining how existing tools are used.
Frying in Your Own Oil with Dr. Neri Karra Sillaman
Q: How do immigrant entrepreneurs build long-lasting businesses with community at the core?
They invest in relationships with suppliers, distributors, and local communities, turning social capital into tangible competitive advantages and sustainable teams that endure through changing conditions.
Frying in Your Own Oil with Dr. Neri Karra Sillaman
Q: What differentiates immigrant entrepreneurs from a leadership perspective?
They tend to avoid the cult of the single 'great leader' and instead center leadership on people, humility, trust, and collective input, which supports durable, value-driven growth rather than ego-driven success.
Frying in Your Own Oil with Dr. Neri Karra Sillaman
Q: Out of the eight principles, which one would surprise people the most?
Many listeners are surprised by frying your own oil, which underscores the importance of self-sufficiency and leveraging available resources to sustain and differentiate a business, especially when external capital is hard to come by.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Gender Skew
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Professions
Age Range
Household Income
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Frequently Asked Questions About Transformative Leadership Conversations

What is Transformative Leadership Conversations about and what kind of topics does it cover?

This show centers on practical leadership development, coaching, and people-first approaches to managing change and adversity in organizations. Episodes frequently explore actionable frameworks—such as conducting tiny experiments, asking better questions, and embracing rest as a leadership tool—alongside deeper dives into confidence, feedback, and culture. A recurring thread is translating insights into measurable impact for teams and business outcomes, often illustrated with client stories or biomarker-informed leadership research. A standout trait is the blend of pragmatic coaching with science-backed concepts, producing clear, repeatable steps leaders can try right away. Listeners can expect a mix of solo guidance, client case studies, a... more

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Which podcasts are similar to Transformative Leadership Conversations?

These podcasts share a similar audience with Transformative Leadership Conversations:

1. The Mel Robbins Podcast

How many episodes of Transformative Leadership Conversations are there?

Transformative Leadership Conversations launched 6 years ago and published 130 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Transformative Leadership Conversations?

Recent guests on Transformative Leadership Conversations include:

1. Carly Valancy
2. Leah Henck
3. Dr. Angela Stopper
4. Julie Silverman
5. Martin Redigolo
6. Jan-Philipp Martini
7. Elliot Felix
8. Dr. Gwendolyn Freed

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