There has been both a historic and continuing interest in the preparation process for school administrators (principals and vice principals). Much of the literature has been critical of how school administrators are prepared (Achilles, 1991; Hale and Moorman, 2003; Levine, 2005; Hallinger and Lu, 2013). Although the length of time from graduation to hiring was explored, little attention has been paid to the satisfaction of graduates from principal preparation and the number of years that transpired from graduation to job placement. An unknown outcome in the literature on principal preparation programs is the impact of satisfaction in relation to the length of time in securing an administrative position. This article attempts to provide some insight into the relationship.