Although constituting a significant position in the daily practices and development of many school organizations, little is known regarding how the position of the deputy principal is organized. The purpose of this paper is to explore how Swedish principals organize for the deputy principal position by focusing on the triggers and factors constituting their sensemaking of the division of responsibilities. The paper provides an additional perspective by focusing on the interpretive aspects comprising the organizing processes. The paper draws from qualitative interview data from a larger study on deputy principals’ position in the Swedish school system. The results show how principals’ sensemaking is triggered by contextual cues and reform-driven factors that together create spaces of ambiguity in relation to the organizing of the deputy principals’ position. Principals make sense of these events based on personal- and identity-oriented beliefs, as well as frameworks and perceived expectations from municipal organizers.