To inform the development of recommendations to facilitate learning of skilled doctor–patient communication in the workplace, this qualitative study explores experiences of trainees and supervisors regarding how trainees learn communication and how supervisors support trainees’ learning in the workplace. We conducted a qualitative study in a general practice training setting, triangulating various sources of data to obtain a rich understanding of trainees and supervisors’ experiences: three focus group discussions, five discussions during training sessions and five individual interviews. Thematic network analysis was performed during an iterative process of data collection and analysis. We identified a communication learning cycle consisting of six phases: impactful experience, change in frame of reference, identification of communication strategies, experimentation with strategies, evaluation of strategies and incorporation into personal repertoire. Supervisors supported trainees throughout this process by creating challenges, confronting trainees with their behaviour and helping them reflect on its underlying mechanisms, exploring and demonstrating communication strategies, giving concrete practice assignments, creating safety, exploring the effect of strategies and facilitating repeated practice and reflection. Based on the experiences of trainees and supervisors, we conclude that skilled communication involves the development of a personal communication repertoire from which learners are able to apply strategies that fit the context and their personal style. After further validation of our findings, it may be recommended to give learners concrete examples, opportunities for repeated practise and reflection on personal frames of reference and the effect of strategies, as well as space for authenticity and flexibility. In the workplace, the clinical supervisor is able to facilitate all these essential conditions to support his/her trainee in becoming a skilled communicator.