Episode Five: When Leadership Gets Heavy with Dr. Kurt Senske

In this episode of The Upside Down Leader, Billy Moyer sits down with Dr. Kurt Senske, founder of CEO Board Services and former CEO of Upbring, for an honest conversation about leadership under sustained pressure. With more than two decades leading mission-driven organizations, Kurt shares what it means to carry responsibility when the stakes are high and people are counting on you.

Together, they explore how stress subtly reshapes a leader, first through overwork and hyper-focus, then through cynicism, sarcasm, unhealthy habits, and isolation. Kurt reflects on seasons of self-doubt, bad hires, external crises like Hurricane Katrina, and even receiving “CEO of the Year” while privately feeling like a fraud. The conversation dives into board relationships, the increasing complexity of executive leadership, and the importance of accountability partners who can call you back into alignment.

This episode is a grounded reminder that leadership isn’t about accolades or endurance. It’s about clarity, integrity, and building habits that keep you from drifting too long into the Upside Down.