The supervisor-trainee relationship is fundamental in ensuring the best continuing education for all trainees. One of the key skills of supervision is being able to communicate effectively; however, this is sometimes difficult. In this article we explore how two transactional analysis models, the Drama and Winner's triangles, can help supervisors work and communicate more effectively with trainees. All supervisors will have had a 'heartsink moment' before meeting a known trainee. The models can be used to explain these situations and what exactly is happening to the communication. The models provide methods of breaking free from these frustrating encounters and moving on with the relationship with your trainee. The models also help us understand the ways in which we can easily be pulled into games and offer insight into our own behaviours and relationships, not only with trainees, but also with patients, carers and colleagues. Real life scenarios are used throughout to explain the models.