Is bigger always better? Not so fast. In this episode, I sit down with Jonathan Bennett—former hospital exec turned consultant and coach—to talk about what happens when growth leads to burnout, how boards can shift from control to connection, and why slowing down might be the smartest move your nonprofit ever makes. We explore strategy, leadership transitions, and the power of authentic relationships—in and out of the boardroom.

Episode Highlights

• 02:16 Career Journey and Insights

• 07:04 Importance of Organizational Alignment

• 14:48 Governance and Relational Leadership

• 20:19 Indigenous Approaches to Meetings

My guest for this episode is Jonathan Bennett. He left an executive role at a large hospital to strike out on his own, founding a management consulting firm. And, for 10 years, things were great. The company grew–became a B Corp and served hundreds of organizations. The problem was, he was unfulfilled.

After a successful exit in which he went through a management buyout of his company, Jonathan founded his coaching practice so that he could fulfill his purpose to create an intimate space for leaders who need to be listened to deeply.

Jonathan Bennett is an advisor and executive coach for founders, CEOs and C- Suite leaders who have a purpose in the world but need help solving their organization’s toughest obstacles.

Jonathan takes his experience as a CEO, board member, and founder to his coaching. As a feminist and social justice advocate, Jonathan brings a progressive approach to his work so that clients always find a way out of even the most complex challenges.

He resides in Ontario, Canada with his family and two dogs. A published author, he’s written seven literary books.

Connect with Jonathan:

Website: clearlythen.com

LinkedIn: www.linkedin.com/in/bennettjonathan/

Private Podcast: https://clearlythen.com/listen

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