This empirical study explores how international school directors find novel ways to develop and lead through ambiguity. The research examines whether and how international school leaders' abilities to perceive, experience, and navigate ambiguity are linked to their stage of ego development. It investigates what kinds of internal and external conditions and capacities can support transformative outcomes for leaders and their school systems when facing ambiguity. Research shows leaders in international schools face unique challenges amidst complexity. This study examines directors' meaning-making using semi-structured, narrative interviews and the Leadership Development Profile (LDP) to understand the relationship between leaders' developmental stage and their capacity to productively navigate ambiguity for personal growth and organizational transformation. Research participants include 13 directors of nonprofit international schools. A constructive developmental lens provides insight on transformative leadership development. This research has implications for international school leadership, adaptive leadership, transformative learning, and constructive-developmental theory. Findings reveal that leaders at later action logics demonstrate more sophisticated strategies for navigating ambiguity, including reframing challenges as opportunities, fostering collaborative ecosystems, and leveraging emotional intelligence. Novel approaches include developing adaptive leadership skills, cultivating perspective-taking abilities, and engaging in reflective practices to enhance self-awareness and cultural sensitivity. [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.]