This narrative study examined the experiences of four school district leaders as they led a technology-based change initiative in their respective school districts. This study incorporated Sandy Kristin Piderit's change ambivalence theory as the theoretical framework, which provided a lens for this research study. The central research question guiding this study was: What is the nature of technological change ambivalence as perceived by school district leaders, and more specifically; how do leaders overcome ambivalence to lead a successful and sustained technology initiative within their school districts? The findings revealed that the technologybased change initiatives that the four participants led were very strategically planned and implemented, including aspects such as clear goals, stakeholder readiness, professional development, methods for monitoring success, and reflections. The findings also showed that they did experience ambivalence and the types of resistance that is tied to ambivalence as they implemented their initiatives. As a result, school leaders employed specific strategies to help overcome resistance and support resistors. Additionally there were a number of consistent steps that the school leaders took that led to the successful implementations of their initiatives, which in many cases also served to proactively prevent resistance that may have occurred.