Principals can have a positive impact on student achievement by employing specific actions targeted at improving teaching and learning. District offices can have a positive impact by helping principals develop and grow as leaders, but how and under what conditions? While growth and development are entwined with relationships, little is understood about the relationship between principals and their supervisors, the focus of this study. Through interviews in four suburban school districts, a grounded theory emerged that described the relationship needed for superintendents (and others who lead principals) to play a meaningful role in principals' growth as leaders. A trusting relationship was a pre-requisite to facilitating principal growth through a balancing of "push" and "support". However, this trusting relationship (from the principals' perspective) was more elusive and required more intentionality than many supervisors understood. The grounded theory that emerged from this study details the specific actions and characteristics that undergird both core concepts of a "trusting relationship" and achieving a balance of "pushing and support". Four actions and four characteristics were identified as critical in establishing a trusting relationship. Five actions and two characteristics were identified as effective in achieving a balance of push and support. Examples of identified actions include "investing time" and "co-creation". Examples of identified characteristics include "vulnerability" and "caring". The ground theory illustrates how the different actions and characteristics interconnect, as well as compares the differences in emphasis between principals and their supervisors. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]