Transformative Leadership Conversations with Winnie da Silva

Transformative Leadership Conversations with Winnie da Silva


The Confidence You Learn with Dr. Angela Stopper

December 10, 2025

“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