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In this special episode of Monday Matters, I had the privilege of sitting down with members of a leadership mastermind group from the Archdiocese of Louisville Catholic Schools in Kentucky. Recorded during Kentucky Derby season, I affectionately referred to this group as my “Derby Mastermind.” Together, we reflected on how collective coaching, mentorship, collaboration, and reflective practice shaped our growth throughout the school year.
Guests Featured:
Throughout the conversation, we discussed how mastermind collaboration helped us:
- Become better listeners rather than immediate problem-solvers
Several leaders reflected on how easy it is in administration to jump quickly into “fix-it mode.” Through coaching conversations and reflective questioning, we learned the value of listening first, seeking to understand root causes, and creating space for people to process their own thinking before offering solutions. - Slow down and reflect more deeply before reacting
The group repeatedly emphasized the importance of pausing before responding to difficult situations. Rather than reacting emotionally or rushing toward quick answers, leaders described learning how to reflect more intentionally, ask deeper questions, and approach challenges with greater wisdom and perspective. - Examine assumptions and refine decision-making
Leadership often requires reevaluating assumptions and seeing situations from multiple angles. Participants shared how collaborative discussion and “hot seat” conversations challenged their thinking and helped them make more thoughtful, nuanced decisions. - Build confidence in their leadership capacity
Some leaders entered the cohort unsure of what they could contribute, especially those newer to administration. Over time, the encouragement, collaboration, and shared learning within the group helped build confidence and reinforced that their experiences, instincts, and leadership voice mattered. - Reduce the isolation that often accompanies leadership
A recurring theme throughout the conversation was that leadership can feel lonely. The mastermind experience created a trusted space where leaders realized they were not alone in their struggles, challenges, or questions. The relationships and shared experiences helped replace isolation with connection and support. - Develop healthier rhythms around reflection, family, wellness, and personal growth
Through recurring reflection questions and accountability practices, leaders became more intentional about balancing their professional responsibilities with personal wellness, family presence, reading, reflection, exercise, and healthy routines. - Translate coaching practices into stronger support for teachers and teams
Leaders shared how they began applying mastermind strategies within their own schools — including celebrating successes, revisiting norms, asking stronger coaching questions, holding reflective conversations, and intentionally developing leadership capacity among teachers and staff.
We also explored how structured reflection, accountability, and collaborative problem-solving influenced our schools. Several leaders shared that the practices modeled during our mastermind meetings — including celebrations, norms, reflective questions, coaching conversations, and clear agendas — became strategies they intentionally implemented with their own faculty and leadership teams.
A recurring theme throughout the episode was that leadership development is not selfish; it is essential. As Trevor Timmerberg reflected, effective leaders invest in themselves so they can better serve others.
Parting Words of Advice from Each Leader
Shelly Pence
“If I don’t invest in myself, then I don’t have the capacity to invest in others. I have to continue to invest in my own growth to be able to invest in other people.”
Chastity Livers
“Take the time to learn and grow. It benefits your school, your professional growth, and even your personal life. I’m always recharged after every mastermind session.”
Jessica Young
“Having an opportunity to collaborate helps you feel supported and stretched. You become a better leader and a better person.”
Dr. Karen Loper
“Give yourself permission to spend the time you need to become a better leader. That’s what we’re all striving for.”
Dr. Trevor Timmerberg
“Investment in yourself as a leader is never superfluous and it’s never selfish. You owe it to the people you serve to put the oxygen mask on first so that you can help others.”
Now It’s Your Turn
Thank you for listening and learning together. When you intentionally invest in your own growth, collaboration, and reflection, you are:
- Learning and growing
- Supported and stretched
- Creating time for renewal and reflection
- Recognizing that leadership growth is not selfish
- Returning to your schools equipped with greater perspective, wisdom, and context
As always, I hope this episode reminds you that leadership is strengthened through collective learning, thoughtful reflection, and meaningful relationships.
If you’re interested in learning more from these leaders, reach out through their websites listed in the introduction. If you’d like to connect about opportunities for coaching, mentoring, or Masterminds for yourself or your leaders, reach out to Will at will@williamdparker.com
Until next time, thank you for doing what matters!
