This qualitative study provided the perspectives of school principals on leading Outstanding Schools in Qatar. The opportunities for establishing a private school in a foreign country are endless, given the increase in the expatriate population and the waiting lists for students to enroll in the existing schools. This study revealed some of the challenges that current leaders of outstanding school are facing due to changes in leadership and organizational structures, as well as to unexpected operational changes that were not part of the initial memoranda of agreement. This study paves the way for scholars, practitioners, and policy makers to support similar initiatives.