The successful supervisor, like the successful executive, is focused on the long term: decisive, inclusive, and personally humble--what Robert Greenleaf (1977, 2002) would call a servant leader. A student affairs supervisor also is a leader, manager, coach, and coworker. These can be daunting responsibilities, especially during times of uncertainty, with reduced budgets, layoffs, and restructuring. Student affairs supervisors are called upon to navigate increasingly complex educational and work environments and new legal developments, as well as the diverse needs, hopes, and dreams of employees. This chapter frames several key areas and challenges of the contemporary supervisory milieu, including financial uncertainties, the timeless importance of trust, and the influence of new technologies on the supervisor-supervisee relationship. Key references and resources that might be of value to supervisors are addressed.