The Hardest Leadership Question with Winnie da Silva

29/10/2025 14 min
The Hardest Leadership Question with Winnie da Silva

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Episode Synopsis

“People do change - sometimes by choice, sometimes by necessity, but always through connection.” - Winnie da SilvaCan 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.ResourcesWinnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]