Many have identified the principalship as a “sink or swim” role (Rooney, 2000, p. 77) in which new leaders address a multitude of tasks daily (Spillane & Lee, 2014, p. 433) with feelings of being ultimately responsible (Swen, 2019, p. 5). Preparing principals through induction programs, internships, mentors, coursework, and exposure, are just some of the many ways that we currently prepare beginning principals for their new role. “Challenges for novice school leaders evolve as information is managed differently and as societal and regulatory expectations change” (Beam, Claxton, & Smith, 2016, p. 145). Given this on-going negotiation, novice principals must actively engage in meaning-making and critical reflection of their broad range of experiences. This research dives into this transitional development, as it relates to school culture and the means through which novice elementary school principals come to understand it. Building on decades of research focused on the work of the principal and how that work can become maximized for efficiency and effectiveness, this dissertation situates the novice principal as a learner within the realities of the school organization’s culture. The identity of a novice principal is mutually defined with multiple factors, including, but not limited to, the people, place, time, and dynamic cultural process of their placement (Rogoff et al., 1995, p. 45). It was the intent of this research to learn how novice principals approach learning about school culture at a site where they have never worked before. Utilizing a cross-case study design, grounded in a social constructivist lens, three principals including a first-year principal, second-year principal and third-year principal participated in two rounds of interviews. The first interview included a set of elements of culture developed by Wagner (1998) that looked at what these novice principals knew about the culture at their sites. The second round of interviews looked at these same questions, but probed for how they learned about each component respectively. Interviews were transcribed, coded based on the framework developed by Wildy and Clark (2008b) which includes place, people, system, and self. Subthemes were also identified, and data were compared across cases and within each case. Results include the acknowledgment that novice principals utilize a variety of approaches to learn about school culture. A majority of these approaches include informal learning such as previous experiences, exposure due to an active presence, and situational learning within the context of place and time. Trial and error, as well as on the job learning, were highly prevalent across interview responses, as well as the identified approaches of observations, purposeful communication, asking questions, listening attentively, and seeking to understand. It is important to continue to build our understanding of how novice principals approach their learning of school culture. Insight into how, when, and why novice principals engage in this learning holds potential for informing and improving school culture, principal preparation, and the development of novice principals in their early years in the position.