Background <p>The assessment of treatment competence among trainees in psychoanalytic therapy training has traditionally been unstructured and based on experience; however, empirically developed catalogs of criteria exist, which capture core competencies across different therapeutic schools. Clinically standardized examination formats are currently being tested. This shift towards empirical foundations is particularly relevant given the current pressures for legitimization in the context of university integration and health policy requirements.</p> Research question <p>How do institute-affiliated supervisors (SV) currently position themselves within the tension between tradition and empirical approaches?</p> Material and method <p>This was explored in a&#xa0;qualitative setting using grounded theory methodology as described by Charmaz. Interviews were conducted with 12 SV regarding their evaluation practices across various formats (e.g. assessments of case history presentations, training treatments, interim and final examinations). Interviewees were asked about challenges and strategies for resolution based on recalled cases. Both “structuring” and “intuitive” evaluation elements were identified. Challenges included negative assessments and disagreements in the evaluation. These challenges could be addressed through structured evaluation, when available. No SV had access to an institutionally mandated structured examination procedure, which would integrate both sides of intuitive and structured evaluation.</p> Conclusion <p>Suggestions are derived for incorporating criteria-based evaluation into current assessment practices, regardless of the examination format.</p>