Through the analysis of semi-structured interview responses from four school principals centered on their implementation of a new competencies based curriculum called Career and Technology Foundations (CTF), we sought to better understand their experience with implementing this new program of studies in its optional year of implementation. Four themes arose: Content Knowledge; Values, Expectations, and Vision; Contextual Considerations; and Decisions, Actions, and Behaviors. By understanding how stakeholders conceptualize new expressions of curriculum, potential programming structures, and related pedagogical approaches, principals can be more prepared to engage in substantive conversations with teachers and provide learning supports that enhance professional capacities.