The purpose of this qualitative study was to explore possibilities for transformational coaching in education through the collaboration and cooperative argumentation of two researchers, one using appreciative inquiry to look at its transformative potential and the other using critical inquiry to investigate possible hegemonic and non-hegemonic barriers to this potential. Each researcher conducted separate research studies. The first researcher performed phenomenological interviews of 7 prominent coaches representing 5 different philosophical approaches to coaching that could enhance the potential for transformation in K-12 educational settings. Data analysis focused primarily on how the individual responses related to each other in terms of commonalities and distinguishing features regarding the phenomenon of the potential for transformation. The second researcher conducted phenomenological interviews of 10 coaches, 9 administrators, and 2 teachers in a single school district that has had an educational coaching program for 7 years. Interview transcripts underwent 3 levels of analysis, from topical organization of the raw data, to a more interpretive categorization of the data, to a final level where the categories of data generated theory about barriers to this district's coaching program. Results of the first research study indicate that holistic coaching approaches can enhance the transformative potential of educational coaching. These approaches require coaches who have achieved advanced levels of emotional maturity, mastery of their craft, and the ability to access "different ways of knowing" to help guide the coaching process. Results of the second study show that two aspects of school and district culture influence the viability of educational coaching: administrators' ability and willingness to understand and facilitate coaches' work, and varying degrees of openness to equitable practice among educators. Some of the barriers are hegemonic and others are not. We conclude that holistic approaches to coaching can offer transformative possibilities for educators. Educational coaches can develop themselves and achieve mastery and effectiveness by drawing from a more holistic and eclectic base of coaching theory and practice. Coaches can and must learn the art of detecting hegemony in others and in themselves to help assure optimal applications of this knowledge toward positive transformation in their schools. Recommendations for further research include research on transformative coaching practices in education, research on the developmental and maturation levels of coaches and their impact on school coaching, and research on hegemony that includes other school districts that represent a wide variety of demographic configurations. (Contains 3 Tables, 3 Figures, 12 Appendices). [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/en-US/products/dissertations/individuals.shtml.]