Although playing by ear has important benefits for the development of musicianship, one-to-one instrumental teaching has traditionally overlooked it. The current research describes the strategies applied by three woodwind teachers with their students in a Spanish music school through a multiple-case embedded study. Data were collected through multiple choice questionnaires, interviews and the observation of lessons. They were analysed according to the strategies applied, the teachers' expertise in playing by ear as performers, and the inclusion of playing by ear in their regular teaching as a result of participating in this research. The results show that the strategies of these teachers, when including some pre-designed tasks in their lessons to develop playing by ear, were influenced by the teachers' biographies and teaching styles. Ultimately, the description of these features may be useful in prospective design of teaching methods aimed at developing playing by ear in instrumental lessons.