This theoretical analysis employs a poststructuralist lens to reveal the constructs behind the word "fit", an oft used descriptor integral to the discourse of school hiring practices, personnel decisions, and politics. Although the term is a part of the everyday culture of school politics, it is rarely considered with any depth. Using the metaphor of a mechanical watch, the authors explain how two theories and a sociopolitical concept (identity theory, social constructionism, and hegemony) conflate the role and responsibilities of leadership with the frameworks of one's identity. Thus, fit is used to perpetuate hegemony and the social construction of what a school leader is. The authors cite empirical examples of how some leaders negotiate their fit and how some leaders are able to transcend the boundaries of tolerance to recreate the definition of "the best fit for the job." Finally, they outline the implications of the politics behind the word "fit", along considerations for those who prepare school leaders, those who are serving as schools leaders, and those policy makers who govern school leaders. (Contains 2 figures and 7 notes.)