The University Council for Educational Administration (UCEA) was founded more than six decades ago to build a knowledge base of research and effective practice for the field of educational leadership. UCEA is a collective of approximately 100 top research institutions with programs in educational leadership and policy and is the leading professional organization for professors in the field. The Center for the Advanced Study of Technology Leadership in Education (CASTLE) is one of UCEA's nine national program centers. CASTLE was founded in 2005 and remains the nation's only academic center dedicated to the technology-related needs of school principals and superintendents. Dr. Scott McLeod is the founding director of CASTLE and is the recipient of numerous national and international awards for his work on digital leadership issues, including the 2016 International Society for Technology in Education (ISTE) Outstanding Leadership Award. Dr. Jayson W. Richardson is a director of CASTLE and also serves as UCEA's associate director of program centers. The questions in this commentary were posed by members of Working Group E of the Jefferson Education Accelerator initiative on the Efficacy of Educational Technology Research.