Objective: This article introduces the prospective leader to a set of questions and relevant leadership literature that aid in the process of deciding whether to accept a leadership position. Method: The author conducted a review of literature and discussion with leaders in psychiatry and other medical disciplines. Results: The questions posed and leadership literature discussed provide a useful set of guidelines for potential leaders in deciding whether to accept or continue in a leadership position. Conclusions: Having access to mentoring, a clear description of "expected results," personal appreciation of leadership style, a description of available resources, a leadership vision in line with the institutional vision, and an appreciation of the necessary time commitments are fundamental in deciding whether to accept a leadership position.