Purpose: The purpose of this paper is to help the researchers sought to take a closer look at the technology challenges facing district superintendents in today's leadership climate. Design/methodology/approach: The authors chose semi-structured interviews as the data collection method. Through 45 min, one-on-one, semi-structured telephone interviews, the researchers were able to collect data about overcoming the challenges of being a modern technology-savvy superintendent. Findings: Through the analysis, the authors identified four themes related to the challenges faced by these district leaders, including meeting the needs of stakeholders, supporting professional development, fostering mindset changes and addressing a fear of the unknown. Research limitations/implications: This study only relied on interviews and did not examine evidence from the field, such as site visits or artifact examination. Practical implications This study provides the field with insights into the role of the change-ready district leaders who foster lasting technology-infused transformation. Social implications: While challenges for any district leader wishing to make long-lasting change exist, there are district leaders today who embody second-order change leadership when overcoming the challenge of school technology leadership. These technology-savvy superintendents play an important role as whole-system change agents. Originality/value: This study highlighted that there many district leaders today who embody second-order change leadership in helping move their districts forward.