In the past 3 decades, we have witnessed the implementation and expansion of online education designed for increasingly diverse audiences worldwide via an impressive array of new instructional media. Many proponents contend that Internet-supported teaching and learning is the most important innovation in education since the printing press. Yet, less favorable critiques of this phenomenon prevail, as some social critics maintain that the introduction of technology into the teaching and learning environment represents a process of disruptive innovation that has not had any truly transformative impact, and indeed, has widened the digital divide. Individuals working in distance education leadership roles face formidable challenges in ensuring that instruction delivered at a distance remains relevant and effective in an evolving digital age. Among the most vexing conundrums is what the editors of this special issue refer to as "technological transience": rapidly changing technology options that can become obsolete just as their users are becoming facile with their use. In this volatile environment, what are the attributes and competencies that are important for leaders to effectively advance and sustain distance education initiatives? This article examines critical issues and essential attributes in the context of technology transience that decision makers must continuously address and practice if they are to provide meaningful and transformative change in the next era of online education.