Leading with Empathy and Cultivating Connection in Leadership with Jerry Colonna

Jerry Colonna is a coach and facilitator known for integrating the principles of self-awareness and mindfulness into entrepreneurial leadership. He is the CEO of Reboot and the author of the influential books Reboot and Reunion. Through his work, Jerry has established himself as a guiding force in the world of leadership, advocating for a harmonious balance between personal well-being and professional excellence. His influence continues to grow as he teaches others to look within themselves to lead with integrity, compassion, and authenticity.

This week, Barrett talks with Jerry about the complex landscape of leadership and the significance of fostering deep connections and a sense of belonging within the business world. They discuss Jerry's belief in merging profitability with social responsibility in business, the value of emotional intelligence and vulnerability in leadership, the challenges and opportunities of coaching, and the importance of looking inward for personal and professional development. They also explore how business leaders can encourage positive systemic change and create environments that prioritize human connection and empathy, paving the way for a stronger sense of community.

In this episode:

[02:46] - Jerry's journey from executive to holder of stories
[03:09] - The power of presence and emotional rapport
[06:53] - Exploring inner work and radical self-inquiry
[09:48] - Learning to hold space for others
[13:57] - The impact of coaching and psychoanalysis on leadership
[20:22] - Embracing pain and grief for personal growth
[26:33] - The journey of healing and letting go
[32:05] - The importance of community and belonging
[39:00] - Confronting social issues and embracing humanity
[46:00] - Reflecting on economic prosperity and its purpose
[46:53] - The role of business in society
[48:17] - Personal stories of business and social responsibility
[49:58] - Why climate change is a global emergency
[50:30] - The human cost of conflict and separation
[53:30] - Leadership, belonging, and the CEO's role
[01:01:31] - The power of ancestral stories and belonging
[01:15:35] - Embracing leadership and creating belonging
[01:16:58] - Tools and insights for effective coaching
[01:25:03] - Envisioning an unbearably beautiful future

Key Takeaways

Leadership is not solely about directing teams; it’s about holding space for the stories of the heart and fostering a genuine sense of belonging among individuals.
Engaging in self-inquiry and acknowledging our full range of emotional experiences is crucial for personal and professional evolution, challenging an outdated philosophy of leaders at arm's length.
By rejecting false dichotomies, leaders can build organizations that are both profitable and deeply committed to social well-being.
Embracing vulnerability by acknowledging personal and collective stories shapes a future of hope that is "unbearably beautiful," and rooted in open-hearted connections.
Through understanding—and learning from—the hardships and aspirations of past generations, we can cultivate profound societal and corporate change for the future.

Quotes

“When you create space for the other person, more often than not, the emotion that rises is sadness. I have come to understand that the sadness is tinged with relief because we live in a world that's acculturated to turning people into problems, turning emotional states into problems, things that need to be changed.” ~ Jerry Colonna

“We are surrounded in our thinking by what I would call false dichotomies. Either we build a healthy, profitable business or we take care of people. Either we build roads and bridges, or we take care of the planet. These are false choices.” ~ Jerry Colonna

“You can step into the place of being able to stand shoulder to shoulder with someone else's story and the fullness of that story without turning it into a problem that you need to solve, without taking the burden of the emotions. It is, in my view, the most profound expression of empathy.” ~ Jerry Colonna

Links