Mid-career students who undertake doctoral studies have often achieved standing and success in their careers and may already hold quite senior leadership positions in the profession. In view of this, mid-career students may struggle with the transition to student, particularly if they have not studied for a number of years and have multiple pressures on their time. Supervisors on the other hand, operate within cultures of performance based indicators, and are under pressure to facilitate timely student completions. While students must take ultimate responsibility for their doctoral work, it is possible for supervisors to identify problems early, and offer practical solutions to assist mid-career students overcome their problems, and facilitate optimal engagement. In this paper we highlight some of the challenges this vulnerable student group can present, and identify some practical strategies supervisors can suggest to assist in the timely and successful completion of doctorate degrees.