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 middle school teacher, school district administrator, and nonprofit leader, providing a unique perspective on how communication, trust, and collaboration drive meaningful change.  Throughout his career, Will has led efforts to expand college access, strengthen career pathways, and improve outcomes for young people. He is passionate about bringing people together across diverse perspectives to solve complex problems and create lasting impact.  Will believes that many of the most important breakthroughs in organizations and communities begin with honest, courageous conversations. He has led teams through periods of growth, uncertainty, and transformation, and has seen how empathy, curiosity, and clarity can strengthen relationships and move people toward shared goals.

Contact us: 

• Email – [email protected]
• Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders
• Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment