Effective supervision contributes to a higher quality of social services and supervisees' professional development. Lack of adequate training in applying supervision skills can be a problem not only for social work supervisors, but also for the social work practice delivered by their supervisees. This study examines the process of transition from being a frontline worker to a supervisory role with a focus on the skills, knowledge, and abilities essential to the preparation of this transition. Bridges' (2009) Transition Model guided the exploration of the concepts and processes of supervision. This study included qualitative data from 24 supervisor participants from different work settings in Houston, Texas. Semi-structured in-depth interviews were conducted in person or by phone/Skype with each consented participant. All interviews were audio recorded and fully transcribed verbatim in English for data analysis. Hycner's (1978) phenomenological method was employed in the analysis. Findings included three themes: challenges, facilitators, and needed trainings within the supervisory transitioning process. The most significant challenges included peer to supervisor transition, an overwhelming workload, unclear role expectations, and managing seasoned staff. Facilitators for ease of transition included formal trainings, self-education, familiarity with the agency, supportive supervisors and team, and peer coaching. Nearly all participants discussed the need for more trainings in the areas of leadership and management, administration, and finances. This study recommended more research to test the effectiveness of current leadership training, a policy to establish requirements in general social work supervision such as leadership training, agency-sponsored supervision courses, and continuing education for social work supervisors. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]