During the COVID-19 global pandemic, there was no precedence set or documented protocol to govern the transition from face-to-face to online teaching. The purpose of this study was to explore middle school administrators' perspectives on their challenges and opportunities when assisting teachers as they transitioned from face-to-face to online teaching during the COVID-19 pandemic. Bass's transformational leadership theory was used as the conceptual framework to emphasize the need for administrators to motivate teachers to persevere and adapt during times of crisis. The study's two research questions were designed to explore administrators' perspectives on whether they experienced challenges or opportunities when assisting teachers during the COVID-19 pandemic. The research design was a basic qualitative approach and semistructured interviews were used to collect data from 10 participants who had been administrators for at least 2 years before the pandemic. The interviews were conducted using an online platform, recorded, transcribed, and coded to yield four themes, revealing that administrators employed empathy to further common organizational goals by cultivating interpersonal relationships, established supportive cultures through effective school leadership, and promoted growth opportunities. The research has the potential to elicit positive social change as it illustrates a practical implementation experience that highlights the importance of administrators creating supportive cultures that build trust and promote teacher efficacy, providing opportunities for personal and professional growth, and fostering sustainable school cultures during times of crisis. Future researchers may wish to conduct the study in an elementary or high school setting as the findings were specific to the middle school environment. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]