Transformative Leadership Conversations with Winnie da Silva

Coaching Teens into Leadership with Lorraine Connell
“Leadership isn’t about being perfect or popular. It’s about making decisions, taking responsibility, and developing the skills that allow us to show up with courage and confidence.” - Lorraine Connell
Are we unknowingly holding kids back by tying leadership to titles, popularity, and perfection? Could our entire approach to teaching leadership be setting young people up to fail before they even begin?
In this episode, I sit down with Lorraine Connell, former chemistry teacher turned teen leadership coach and founder of Peers Not Fears. Lorraine shares how her own experience of feeling “average” in school shaped her deep commitment to redefining leadership for young people. Together, we explore what happens when we empower teens before they’re handed official titles and how we can help them develop confidence, decision-making, and real leadership skills - long before they enter the workforce.
You’ll hear us discuss:
- How our myths around leadership - like needing a title or being perfect - hold kids (and adults) back
- Why Lorraine believes the only true requirement for leadership is the ability to make a decision
- The damage caused when we make student leaders into role models who aren’t allowed to fail
- How mistakes (including Lorraine’s own) became the turning point for creating Peers Not Fears
- The power of peer mentoring and why it’s more impactful than top-down leadership
- Why confidence and leadership are inseparable - and how labeling kids can stall both
- What leadership development actually looks like between ages 12 and 16
- How games, group coaching, and creative challenges open teens up to growth
- What adults need to remember about owning mistakes and modeling leadership
- How to reframe leadership not as a ladder—but as something wide enough for everyone
Resources
Lorraine Connell on Peers not Fears | ''Leadership for Our Kids!'' Facebook Group | Lorraine's books on Teenage Leadership I LinkedIn
Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org