Leading With Courage, Grace, and Community: Rosie Drumgoole
“IT IS NOT ANYBODY’S JOB TO TAKE CARE OF YOU WHEN YOU ARE THE LEADER.”
Episode Description
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.
Chapters
- 00:00 Welcome to Leadership Matters
- 00:33 Growing Up Alongside a Social Worker Mom
- 02:30 How Improv Builds Leadership Skills
- 04:05 The Mentor Who Pushed Rosie to Lead
- 07:33 Leading When You’re Not the Expert
- 11:24 Rosie’s 16-Year “Marriage” to Chicago Cares
- 14:28 Falling in Love vs. the Long Haul of Leadership
- 17:16 The Legacy Behind “World Domination”
- 21:17 What Volunteers Teach Us About Humanity
- 24:45 Seeing Your Team as Whole People
- 27:26 Balancing Accountability and Grace
- 29:50 Why No One Takes Care of the Leader
- 32:36 Why Self-Care Isn’t Optional
- 34:13 What Self-Care Looks Like Right Now
- 35:58 Closing Thoughts
More In The Series
See all on Youtube
