Balancing empathy and performance in leadership
From The Art and Science of Difficult Conversations by Chris Wong & Lucie Tesarova
June 9, 2026 · 39 min · Season 3
About this episode
The episode explores the tension between empathy and performance in leadership through a conversation with nonprofit leader Will Hobart.
How do you align a team that doesn't seem to be reading the same page, or even the same book? In Part 1 of our conversation with nonprofit leader Will Hobart, we dig into one of the hardest tensions in leadership: caring deeply about your people while still driving toward clear goals and results. Will shares the lessons that shaped him, from a fifth-grade conflict-resolution program to the rigid, resource-constrained world of public education, to scaling a 90-year-old nonprofit. Along the way, he gets honest about the moment hard feedback forced him to confront the gap between his intent and his impact, and how he learned that his team's different needs and ambitions weren't a lack of drive but just a different seat at the table. If you've ever felt pulled between the strategy you're accountable for and the empathy your team needs from you, this one's for you. About our guest: Will Hobart is an education leader, strategist, and nonprofit executive with more than 15 years of experience helping organizations navigate complex challenges, build strong partnerships, and create opportunities for student success. His career has included roles as a…
People in this episode
Hosts: Chris Wong, Lucie Tesarova
Guest: Will Hobart
Topics covered
- leadership
- empathy
- performance
- team alignment
- nonprofit
- communication
Keywords
- leadership
- empathy
- performance
- team dynamics
- nonprofit leadership
- communication
- feedback
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