• Mastermind

Jerry Colonna on the Future of Learning


Jerry Colonna is CEO & Co-founder of Reboot.io, an executive coaching and leadership development firm, and author of REBOOT: Leadership and the Art of Growing Up. For nearly 20 years, he has used the knowledge gained as an executive, venture capitalist, journalist and a board member for 100+ organizations to help people lead with humanity, resilience, and equanimity. Listen to his conversation with Candice Faktor about:

  • Why Jerry’s lessons on radical self-inquiry and reflection can help make us better humans and ultimately better leaders

  • Jerry’s key insights on how to lead amidst chaos and uncertainty

  • What the pandemic has taught Jerry and the leaders he coaches about “rebooting”

  • How Reboot, Jerry’s well renowned leadership school, is adapting to virtual and remote learning experiences

  • What Jerry believes the future of leadership education and learning will look like post COVID

Key Moments:

04:05 – What Jerry’s company, Reboot, does and why it’s important for leaders

06:39 – Jerry’s personal story that led him to start Reboot

10:29 – On Jerry’s guiding principle of radical self-inquiry and how it connects to our sense of self-worth

14:22 – Why the concept of radical self-inquiry is so important in the leadership development process especially when leading in uncertainty

18:24 – On how we as humans learn best and why often it requires us to confront our own suffering

21:44 – How Reboot embraces the idea of conscious leadership in their coaching practices and why it is so effective for people who hold so much power

26:32 – Jerry demonstrates why shared experience and how this can make a leader feel more resilient and less lonely

32:50 – The misconception that being vulnerable means showing weakness

34:47 – What Reboot covers at their leadership bootcamps

37:02 – On how Reboot has integrated virtual learning in their bootcamps and why community dedicated learning is the most important aspect

41:10 – The most important lessons Jerry’s clients are learning from COVID

44:48 – Why COVID has given us an incredible opportunity to correct the injustices existant in our society and why this is important for the future of learning

Q&A from Gamechanger/Mastermind Audience:

47:41 – On how parents can best support their kids to be resilient and have a sense of self-worth as they grow up

50:22 – How direct reports can help in making leaders feel safe

52:48 – How Jerry approaches difficult conversations with those who have conflicting opinions

56:18 – On the crucible moments that often lead Jerry’s clients to seeking his help