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To facilitate patient growth, therapists must immerse themselves in the patient’s world while also being able to see what is needed for change. This process requires finding a delicate balance between supporting and pushing patients. Therapists in training are additionally tasked with incorporating supervisors’ suggestions with their own views on what is needed to help their patients. Beginning therapists with tendencies to be overly accommodating may struggle to reconcile these competing demands. Thus, the aim of the present work is to explore how trainee friendly submissiveness (FS) interfaces with psychotherapy. Prior to training, clinical graduate trainee (n = 35) FS was assessed using the Inventory of Interpersonal Problems-32. Process and outcome data were then collected from each therapist’s first training case. Specifically, each trainee was assigned an undergraduate student volunteer with whom they had four non-manualized therapy sessions over the academic semester. After the third session, patients and trainees completed questionnaires assessing session impact and the working alliance, and two expert raters coded third session videotapes for techniques. Following termination, patients rated the overall helpfulness of the therapy. Trainee FS was significantly negatively associated with patient-rated depth, alliance, and overall helpfulness with moderate effects. Findings from a mediation analysis further suggested that trainees with higher FS struggled to focus the therapy in a way that felt productive to patients. Implications for clinical training are discussed.