Introduction: In competency-based medical education, direct observation (DO) of residents’ skills is scarce, notwithstanding its undisputed importance for credible feedback and assessment. A growing body of research is investigating this discrepancy. Strikingly, in this research, DO as a concrete educational activity tends to remain vague. In this study, we concretised DO of technical skills in postgraduate longitudinal training relationships. Methods: Informed by constructivist grounded theory, we performed a focus group study among general practice residents. We asked residents about their experiences with different manifestations of DO of technical skills. A framework describing different DO patterns with their varied impact on learning and the training relationship was constructed and refined until theoretical sufficiency was reached. Results: The dominant DO pattern was ad hoc, one-way DO. Importantly, in this pattern, various unpredictable, and sometimes unwanted, scenarios could occur. Residents hesitated to discuss unwanted scenarios with their supervisors, sometimes instead refraining from future requests for DO or even for help. Planned bi-directional DO sessions, though seldom practiced, contributed much to collaborative learning in a psychologically safe training relationship. Discussion and conclusion: Patterns matter in DO. Residents and supervisors should be made aware of this and educated in maintaining an open dialogue on how to use DO for the benefit of learning and the training relationship.