Purpose: The purpose of this paper is to share lessons learned and tools developed that teachers can use to build pedagogically sound online courses. Transitioning to online instruction is not learning to teach all over again, and it does not have to feel that way either. Through the lens of three common questions new online teachers ask, the principal of a university-run online high school offers practical advice for transforming current pedagogical practices into effective online teaching. This transformation is structured with an innovative "multi-level" approach to assessment. This structure helps organize the transformation, letting teachers focus on building and/or maintaining crucial relationships and meaningful learning experiences with their students. Design/methodology/approach: An innovative assessment lens structures the transformation of practices from brick-and-mortar to online settings, clearing the opacity of the online teaching context so that teachers can return their focus building relationships and meaningful learning experiences with their students. Findings: The paper offers immediately-implementable strategies for designing online courses that facilitate relationship building, meet curricular goals, and are pedagogically sound. Practical implications: Teachers can adapt the tools, resources, and advice included in this paper to fit their unique teaching needs as they move to online teaching contexts. Originality/value: This paper uses the pedagogical model and assessment lens developed by the university-run high school and its principal to offer unique, practically implementable strategies for transitioning from brick-and-mortar to online teaching in this tumultuous time.