Superintendents' instructional leadership is critical to the academic success of school systems. In addition to traditional work complexities, today's superintendents must navigate rapid and significant technological transformations. In this study, an exploratory sample of "technology-savvy" superintendents was interviewed to ascertain advice about how to navigate the complexities that surround successful district-level technology leadership strategies and mind-sets. Participants highlighted issues such as budgets, professional development, and instructional leadership, and affirmed the value of personally modeling technology use. They also emphasized both personal and organizational risk-taking and shared how communities of practice can help alleviate skill and knowledge gaps.