The purpose of this study is to explore the leadership gap that exists between instructors and academic leadership that prohibits students from being successful in online courses, which is the result of academic leaders who inadequately prepare faculty. This is a leadership gap because programs should be established by the administrators to ensure all avenues of learning are addressed. As the enforcers of the college's strategic plan, academic leaders should be held accountable for training the staff to teach growing numbers of online courses. Students' experiences in online learning are a direct result of the instruction they receive. However, instructors can only educate students based on the knowledge and training they receive. Furthermore, academic leaders should employ strategies to bridge the gap between the instructor and the online learning platform. The skills approach to leadership as outlined by Robert Katz (1955) is useful in examining the challenges and experiences of the instructors and how those apply to the characteristics of a leader. A skills leader possesses three different abilities: technical skills, human skills, and conceptual skills (Katz as cited in Virkus, 2009). The skills-based leader recognizes that a particular knowledge base is needed in order to conduct an institution effectively.