Chris Johnson, president and CEO of Portico Benefit Services, joins Kaylee Thomsen to discuss the “wisdom scars” shaping his leadership—from failed launches and hypergrowth to building trust in faith-driven organizations. He shares why leaders must welcome candid feedback, reduce fear, delegate with intention, and make time to think. Chris also explores healthcare costs, GLP-1 coverage, and the responsibility of leading with transparency at work.

Dr. Joseph Lee, president and CEO of Hazelden Betty Ford Foundation, joins host Kaylee Thomsen to explore what addiction recovery can teach us about leadership. He shares why language matters, how listening strengthens relationships, and why empathy can guide decisions. The conversation also covers rebuilding community, following your values, and viewing ADHD as a source of focus and purpose. His message is hopeful: people really do get well.Ask

In this episode of Leadership Matters, Rosie Drumgoole, CEO of Chicago Cares, joins host Kaylee Thomsen to share the people and experiences that shaped her servant leadership. Rosie reflects on growing up alongside her social worker mom, learning to commit to the bit through high school improv, and the mentor who pushed her to say yes to the CEO role. She also explores leading when you’re not the expert, her 16-year “marriage” to Chicago Cares, seeing people as whole and creative, and why self-care is a leader’s responsibility. If you believe great leadership starts with listening, courage, and community, this episode is for you.