Objective: Contextual factors are known to influence the acquisition and application of communication skills in clinical settings. Little is known about residents' perceptions of these factors. This article aims to explore residents' perceptions of contextual factors affecting the acquisition and application of communication skills in the medical workplace. Method: We conducted an exploratory study comprising seven focus groups with residents in two different specialities: general practice (n= 23) and surgery (n= 18). Results: Residents perceive the use of summative assessment checklists that reduce communication skills to behavioural components as impeding the learning of their communication skills. Residents perceive encouragement to deliberately practise in an environment in which the value of communication skills is recognised and support is institutionalised with appropriate feedback from role models as the most important enhancing factors in communication skills learning. Conclusion: To gradually realise a clinical working environment in which the above results are incorporated, we propose to use transformative learning theory to guide further studies. Practical implications: Provided it is used continuously, an approach that combines self-directed learning with observation and discussion of resident-patient consultations seems an effective method for transformative learning of communication skills.