How Leadership Confidence Gets Tested with Winnie da Silva

“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