The fundamental social problems plaguing education are "wicked" (Rittel & Webber, 1973), for they are challenging, messy, and multifarious. Currently, very few problems of this magnitude are solved independently within one school entity. Instead, school leaders routinely find themselves cooperating with leaders across sectoral boundaries to resolve diverse issues requiring input from multiple perspectives. Given the complexity of the problems themselves--as well as the issues that stem simply from the practical implications of people working together (time constraints, for example)--school leaders may want to maximize the time they spend interacting with colleagues to plan for and facilitate systemic reform. A prerequisite to capitalizing on such opportunities is a sophisticated understanding of the factors that promote successful collaboration. Collaboration is an ambiguous term, for researchers struggle to define the phenomenon universally. Synonyms for collaboration, such as teamwork, working together, and cooperation, are often used in literature across fields of study, thus muddying readers' understanding of its exact nature. This qualitative study examined the phenomenon of collaboration from the perspective of school leaders who willingly and voluntarily serve as members of an interorganizational body charged with the task of improving students' achievement, transitioning students from school to work, and strengthening workforce development throughout Southwestern Pennsylvania. The Forum for Workforce Development (Forum) is comprised of leaders from school districts, businesses, non-profit organizations, and post-secondary institutions--stewards of change who recognize the need to collaborate for the purpose of solving serious problems affecting the region. The study was conducted to uncover the traits, characteristics, and attributes of the most productive collaborators among Forum members. By learning which personal characteristics the most adept collaborators possess and how the attributes manifest through behaviors, the researcher might propose to all members ways to increase the Forum's capacity. Data were gathered via semi-structured interviews with 12 Forum members who consented to speak about their experiences as collaborators and share their thoughts about collaboration as a phenomenon, in general. Additionally, the researcher analyzed 117 documents written by, for, and/or about the Forum's work to garner an understanding of how the phenomenon, as participants experience it, evidences more tangibly. Data were aggregated, analyzed, and compared against 22 factors identified by Mattessich and Johnson (2018) as critical for fruitful collaboration. As a result of the study, the researcher learned that, although he remains unable to define "collaboration" universally because the term means something unique and personal to each collaborator, he can cite commonalities among participants' perceptions of what it means to collaborate successfully with fellow Forum members. Based upon the results of this study, the researcher recommends that Forum members invite or recruit leaders known to engage readily and thoroughly, ultimately listening actively to colleagues' ideas and suggestions before advancing the work. From a plethora of findings specific to Forum members' interactions emerged his endorsement of forming subcommittees so that collaborators might feel more comfortable participating in open, honest conversations that nurture a sense of collegiality--the first step towards developing trust among teammates. Ultimately, if members display behaviors that demonstrate loyalty to each other, enthusiasm for the collective cause, and a sincere appreciation for unique perspectives, they will fulfill their mission of helping students become productive members of society. [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.]