Doubt has been increasingly perceived as a means of introducing education renewal, particularly within the context of dramatic social change and uncertainty. Nevertheless, little inquiry has been conducted with regard to the doubting process and the principal's role that influences its effectiveness. This lack of conceptualization is particularly serious in light of the growing number of planned educational restructuring efforts that have rarely demonstrated positive outcomes in student achievements. This article explores the doubting process as an emerging concept in school reform. After introducing the concept of doubt and its importance in educational reform, the article exemplifies a secondary school principal who doubted core pedagogical practices. It is argued that inducing doubt, as a means of fostering productive school change, is contingent both on a paradigmatic shift in the principal's role and on continual consideration of school's social, cultural, and political context. Finally, suggestions for future research are presented.