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Critical to a school leadership team, the Assistant Principal role encompasses job responsibilities that are frequently undefined, expansive, and ever-changing. Limited literature on assistant principals reveals a gap in the field regarding job motivation, career satisfaction, and skill sets assistant principals need to help navigate, adjust, and develop as educational leaders. The purpose of this multiple case study was to examine the motivations and transitional experiences of select novice assistant principals after leaving the teacher role and assuming an initial assistant principal position. Findings suggested positioning assistant principals as an important segment of the educational leadership pipeline gives preparation programs and school systems the tools to properly equip assistant principals to navigate, adjust, and develop in the role.