Six questions that instructional supervisors have been faced with and had to respond to during the COVID-19 crisis include: (a) How do we support teachers in the transition from face-to-face to virtual classes and meetings; (b) How do we focus on addressing the needs of teachers while engaged in remote or online learning; (c) How do we maintain communication, contact, and relationships with teachers; (d) How do we celebrate successes as teachers work with students in the virtual world; (e) How do we assess the quality of the teaching-learning process; and (f) How do we plan for the next steps? Within the scholar-practitioner theoretical model, this study narrates how two principals in Texas addressed each of these six questions. The case studies presented could be used as historical accounts, meaning that leaders could learn from their successes and their mistakes as they move to the next phase of reopening schools.