The Hardest Leadership Question with Winnie da Silva

“People do change - sometimes by choice, sometimes by necessity, but always through connection.” - Winnie da Silva

Can 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.

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [e-mail]