Principles-focused evaluation reflects on the change process itself through examination of its underlying principles. The Centre for Advancing Collaborative Healthcare & Education (CACHE) worked to build interprofessional education programs and tools that attended to the Team Primary Care (TPC) principles. Our internally directed principles-focused evaluation, presented here, asks how CACHE adhered to these principles in the programs and tools it delivered to the TPC project. The article's main contribution is the creation of a new concept, organizational critically reflective practice, which describes an approach health leaders can use to mitigate the limitations of short-term initiatives while pursuing transformational change. We propose specific tools and steps that will help health leaders attempting to enact organizational critically reflective practice.