“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 - winnie@winnifred.org

“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 - winnie@winnifred.org

“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