The U.S. schooling system has a long history of failed reforms that lead to schools consistently perpetuating society's inequities. Rigid organizational structure, built purposely to sustain the life of the institution (as if it, and not the children, were the thing whose life mattered), ensures that even the most well-intentioned transformative school leader or community activist will struggle to create lasting change. Barriers created by organizations, laws, and culture are everywhere, acting as obstacles to discourse and progress. Any attempt to rethink schools must include the voices and ideas of marginalized students and families who are often excluded from curriculum, programming, and jobs. Discourse is a social construct that creates and recreates, distributes and redistributes power. So, can discourse be used to span the boundaries that get in the way of reform? In this dissertation, I examined boundary-spanning dialogue as a way to create a meaningfully inclusive leadership process. I used surveys, qualitative network analysis, photovoice submissions, and a series of dialogues based in the methodological tradition of duoethnography. The data was collected over a two-month period at one case study school and analyzed with critical discourse studies. My results revealed and described boundaries, barriers, and bridges within my case study school, leading to two significant findings: (a) that the visibility of boundaries matters deeply in how we span them and (b) that bridges can be built out of multiple levels of critical discourse. In Chapter 5, I propose that leaders: (a) use dialogue to change the way they see organizational boundaries, (b) build organizational bridges out of the five levels of discourse, and (c) critically construct and deconstruct organizational barriers in order to protect the vulnerable and include the marginalized in a leadership that becomes more process than person. [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.]