When considering the challenges therapists encounter with their male clients, perhaps the most daunting tasks occur at the very beginning. Getting boys and men to avail themselves of psychological services is the first challenge. But when men do present, the second challenge is to get them to trust therapists sufficiently enough to share their issues and to form an effective working alliance. This article describes these gender-related challenges from male clients’ point of view, and then elaborates upon effective techniques to help them engage in and benefit from psychotherapy. We suggest that good therapists for men, like good ship pilots, are informed and prepared. They learn the major cognitive and emotional issues they are likely to encounter with their male clients, and develop a variety of ways to help their male clients navigate the tricky psychological issues of their lives. (PsycINFO Database Record (c) 2010 APA, all rights reserved)