The problem addressed was that the process of pairing mentors with new teachers in the Oklahoma career and technical education (CTE) program was ineffective and lacked guiding standards. The purpose of this qualitative multiple-case study was to explore the perceptions of novice CTE teachers and their mentors and administrators in Oklahoma regarding mentor-mentee pairing methods and their mentoring relationship so that effective mentor-mentee pairing strategies and standards could be developed. In-depth, semistructured videoconference interviews were conducted with ten mentors (including two administrators) and six mentees. Three theories of adult learning framed this study: andragogy, self-directed learning, and transformative adult learning. Participants answered questions about their perceptions of mentor-mentee pairings in the Oklahoma CTE program. Data were coded and categorized into patterns and themes. Participants perceived a lack of formal process in pairing mentors with mentees and a lack of formal documentation and accountability. The view was widely held that mentors and mentees were paired by administrators arbitrarily and by convenience. Participants suggested that a mentor-mentee meeting before the start of school would contribute significantly to a good working relationship. The development of a systematic process for mentor-mentee matching was recommended to optimize the benefits of the mentoring relationship. It was recommended that pairing be based on factors such as similarities in field, program, cluster, division, type of experience, or career path, as well as physical proximity, age, gender, and compatibility of personality. Additional recommendations included administrative support and the use of digital technology to connect well-matched mentors and mentees. For future research, long-term studies with larger sample sizes were recommended. A systematic mentor-mentee pairing process could be developed by means of action research. All findings suggested that mentoring was a worthwhile process that should be strengthened and expanded, with systematic and effective pairing as a starting point. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]