As universities prepare educational leaders for twenty-first century schools, the quality and authenticity of the internship experience require both the strengths of university faculty and the expertise of practitioners to create authentic experiences that seek to bridge the theory-to-practice divide. One mechanism to achieve this is through quality mentorship by school- and central-office-based personnel during the internship experience. A central aspect of this professional relationship is the ability for the mentor to provide access to quality activities that will prepare the aspiring leader for his/her first administrative position. This exploratory study examined language utilized by interns in their time logs as well as information gleaned from preliminary surveys of both interns and mentors upon completion of their experience. Findings revealed the complexity of language analysis and revealed a need for understanding activities of interns and interactions with mentors in a contextual fashion. (Contains 3 tables.)