Supervisee development is integral to counselor training. Despite the general acknowledgement that supervisors adopt different styles when supervising counselor trainees at varying levels, there is a paucity of studies that (a) measure supervisee levels using reliable and valid psychometric instruments, other than a broad categorization of supervisees based on their training progression (e.g., master’s level vs. doctoral level, practicum vs. internship, counselor trainee vs. postgraduate); and (b) empirically document how the matching of supervisory styles and supervisee levels relates to supervision processes and/or outcomes. The supervisory working alliance is key to the supervision process and outcome. To test the hypothesized moderation effects of supervisee levels on the relationship between supervisory styles and the supervisory working alliance, the author performed a series (n = 16) of moderation analyses with a sample (N = 113) of master’s- and doctoral-level counseling trainees and practitioners. Results suggested that supervisee levels and their three indicators (self and other awareness, motivation, and autonomy) were statistically significant moderators under different contexts. These findings (a) revealed extra intricacies of the relationships among the study variables, (b) shed light on future research directions concerning supervisee development, and (c) encouraged supervisors to adopt a composite of styles to varying degrees to better foster supervisee growth.