Discussion Questions:
- Rich Stearns says, “Leaders have to make difficult decisions, and difficult decisions require courage.” How have you seen this play out in your own leadership or in leaders you know?
- Tod Bolsinger talks about the pain of disappointing your own people as a leader. Why is this kind of disappointment particularly challenging in adaptive leadership?
- What does it mean to “disappoint your own people at a rate they can absorb,” and how have you navigated this tension in your context?
- Think about a time when you had to stand against those closest to you for the sake of a mission or vision. How did you handle their disappointment, and what did you learn?
- Tod mentions that “to be faithful to the mission and to what God needs for that church, [the leader] needed to make some really hard decisions.” What hard decisions have you observed or had to make for the sake of a mission?
- Markus and Tod discuss the tension for leaders who are “people pleasers.” How can leaders who want to be liked still practice authentic and courageous leadership?
- Tod references the Israelites’ journey from the Red Sea to the Promised Land as a metaphor for transformation. What does this story teach us about the time and courage transformation requires?
- The episode critiques the idea of rallying a loyal group to maintain your leadership without transformation. How do you see this dynamic at work in today’s organizations or churches?
- Tod highlights the importance of surrounding yourself with both friends and partners who challenge and support you. How do you balance these relationships in your leadership life?
- Mentors, friends, and partners are mentioned as sources of courage for leaders. Who in your life fills these roles, and how have they helped you grow as a courageous leader?



