While the expectations and challenges facing K-12 educational leaders are considerable and significantly increasing, the support they receive in training, leadership development, and ongoing support has been limited in range and relevance. Although Cognitive Coaching is not a leadership development program, per se, Cognitive Coaching is a model of coaching that has been highly regarded and frequently requested by administrators, teachers, consultants, and literacy coaches in K-12 education, and the components of this coaching model can serve as a basis for leadership development. Previous research about Cognitive Coaching has highlighted the benefits of Cognitive Coaching for students, teachers, administrators, and people in fields outside of teaching. This qualitative study, in the tradition of interpretative phenomenological analysis, focuses on the experiences and perceptions of five educational leaders both in being coached and in using Cognitive Coaching as part of their leadership practice. For these leaders, the story behind mastering the skill and not the concept includes engaging in what is simple but not easy, daring to be vulnerable, embracing service and authenticity, and leaning into the value practices of leading with a learning mindset, confident humility, self-awareness, mindfulness, and intentionality to align their behavior with their values. The findings indicate that Cognitive Coaching is about more than cognition; it is rooted in affect and values. Embracing vulnerability is foundational to Cognitive Coaching and leading as a Cognitive Coach. To get to daring vulnerability, Cognitive Coaching leaders need to be authentic and have service at the heart. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]