This exploratory, qualitative multiple-site case study examined principals’ expectations of teaching practices and children’s learning for early elementary grade levels (K, 1st, 2nd, and 3rd). Specifically, this study investigated principals’ understanding of developmentally appropriate practices regarding instructional methods, curriculum content, and assessment strategies. This study also examined how these constructs impact leadership decisions and offered contextual examples to exemplify their influence in real-life situations. Data collection included different school configurations (i.e., PreK-1st grade, PreK-3rd grade, K-5th grade, PreK-8th grade), and consisted of multiple data sources – school observations, teacher and principal interviews, questionnaires, teacher evaluations, a video clip, and artifacts. The twelve guidelines of Developmentally Appropriate Practices (DAP) and the Professional Standards of Educational Leaders (PSEL) provided a framework for thematic analysis. Results indicate principals have minimal training in early childhood pedagogy which may impact teacher evaluations and hiring practices. Results also suggest principals’ explicit leadership decisions conflict with DAP (utilization of external rewards, elimination of art, elimination of play, insufficient reporting measures, etc.). These leadership decisions may inhibit student growth, learning, and development including opportunities for self-regulation. Principals’ implicit leadership decisions may also be promoting inappropriate instructional practices (i.e., prescribed curriculum, teacher-directed whole group instruction, lengthy computerized testing, etc.), but data suggests external influences could be a factor as well. Policy implications and practice recommendations are included.