The purpose of this study was to explore and analyze how district superintendents foster and build relationships with school principals through their interactions to support and nurture strong leadership. From a transformational lens, I explored how the strength of such connectedness builds bridges to leadership sustainability. Reflections of current superintendents are critical to building strong bridges to facilitate the growth and development of future school leaders while meeting the needs of children and families in the school district. The landscape of the superintendency has become so complex, from societal demands and social unrest, that it is imperative for thoughtful consideration of effective leadership that builds potent relationships to successfully meet the needs of an increasing complex population of diverse learners. This study was a basic qualitative approach to examine the superintendent-principal interactions. I collected data through semi-structured, virtual interviews. This approach enabled superintendents to reflect on their leadership practice with principals. Themes that emerged from the interviews included modes of communication, systems of support, and systems of assurance. This study showed the importance of building relationships for current and aspiring superintendents and its impact on their interactions with principals. It informs professional practice and also contributes to the scholarly community by highlighting the contributions of building relationships in leadership roles. [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.]