With an increase of online teaching, social media, and use of classroom technology by both location-bound and distance students, how do educators teach and learn leadership through online tools? The International Leadership Association (ILA, 2009) guidelines, specifically the overarching questions for teaching and learning, provide direction in how to push programs to reach out to all students, especially digital natives. In this chapter, the author explores different technologies and provides suggestions on how to best leverage these tools for maximum student engagement in leadership education.