Since 1970, with the passage of Act 195 of 1970, collective bargaining in Pennsylvania has been an integral process in public schools (PSBA Bulletin, 2010). The success or failure of that process extends beyond the contract's duration; it becomes engrained in the school's culture and is noticeable to those who work, study, and live within the boundaries of the school district. The school district and union leaders' relationship provided the focus of this study by examining the way in which collaborative bargaining took form, grew, and became sustainable. Specifically, this qualitative case study examined three public school districts in Pennsylvania that successfully transitioned from traditional to collaborative collective bargaining. By sharing their vast experiences, the participants of this study--distinguished as outliers, those who employed collaborative bargaining approaches--identified strategies and best practices for bargaining. Additionally, through the theoretical framework of "The Leadership Challenge," by Kouzes and Poser (2012), this study explored the traits and approaches of the school district and union leaders who encouraged and nurtured the transformation from traditional to collaborative collective bargaining. [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.]