This study examines the first-year experiences of new associate deans at doctoral granting, Research I universities. Participants were 24 associate deans from various disciplines at three difference universities who had been in their positions for five years or less. Findings show that the transition into the associate dean position is stressful and difficult, and that the first year involves a great deal of on-the-job skill acquisition, learning to navigate the broader organizational environment, dealing with significant changes in the nature of their interactions with colleagues from their previous departments along with a great sense of loneliness and isolation, and a need to establish new peer groups. However, nearly all report high job satisfaction and a desire to remain in administration. Future study is necessary to examine how these early experiences shape decisions to move into higher-level positions in higher education administration.