Technology has changed the way people live, from use of the Internet to the way they communicate with text messages and e-mails. This change is also evident in the education system. This study traced how principals' leadership roles have changed in the school setting because digital natives and society, in general, have become technologically savvy. The findings for this study were generated from interviews and observations of high school principals. This qualitative research study revealed that administrators are apprehensive about social media in the classroom and that they need to become more familiar with it to better implement technology effectively in the classroom. To ease their apprehension, principals need to change their ways of thinking about social media's use. Professional development in technology skills needs to be more available and flexible for principals to become a more visionary technology leader in the 21st digital educational environment.