Being busy can feel like progress. Having answers can feel like confidence. Keeping your door open can feel like good leadership. But when was the last time you stopped to question whether those habits are helping you lead?
Dr. Christopher Jones returns to Leaning Into Leadership after first joining the show in episode 42. A veteran high school principal, Chris brings honest stories and practical ideas from his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself.
Together, Darrin and Chris explore the stages of leadership development through an unexpected lens: the riddle of the Sphinx. From crawling through the unfamiliar challenges of a new role to finding your stride and supporting the leaders coming behind you, each stage requires reflection, humility, and a willingness to keep learning.
Chris also challenges the belief that effective leaders must always have an open door. He shares why protecting time to think is essential to serving your school well—and how to help your team understand the purpose behind that boundary.
The conversation turns personal as Chris recounts receiving an anonymous, hurtful card when leaving a school. His experience opens a discussion about responding to criticism, recognizing patterns in feedback, and asking what you might need to learn before allowing defensiveness to take over.
In this episode, we discuss:
Whether you’re stepping into your first leadership role or have spent years in the principal’s office, this conversation offers an invitation to examine your habits and keep growing with intention.
Connect with Dr. Christopher Jones
Find Chris on Instagram at @drcsjones and explore his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself. Revisit episode 42 for his first appearance on Leaning Into Leadership.
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