Effective teacher-student learning relationships can propel students to advanced ways of knowing and acting. In much arts based higher education learning, dynamic and fluid interplay of cognitive, meta-cognitive and aspirational aims and goals are prevalent and passed to students in a learning relationship that can be described as a cognitive apprenticeship. Interpretative phenomenological analysis is used to explore four conservatoire teachers and their musical improvisation students. Investigating in the lesson experiences reveal pedagogical applications of modeling, scaffolding, coaching, reflection and developing mastery and expertise in students. A cognitive apprenticeship model can provide a framework for teachers to understand how to develop increased student control, ownership of learning, and contextually situated instructional strategies that brings cognitive and creative thinking, action and reflection to the forefront of learning and teaching. The study reveals how educators can develop trajectories of learning and problem-solving concepts that draw students into a culture of expert practice.