Customary practice in schools is that educators work in silos, often neglecting the opportunity to collaborate with colleagues to truly meet all students' needs. As students transition from middle school to high school, a clear bridging process is vital to set students up for success. Conventional parameters will need to be dismantled, and outside-of-the-box thinking will need to come to the forefront to provide a collaborative learning environment for all stakeholders. This paper discusses the impact that leadership coaching had on facilitating collaboration between the principals of three middle schools and one high school, with an overall goal of establishing a clear bridging process to support first year high school students. [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.]