One goal of student affairs programming is the promotion of character development. Based on the assumption that empathy training will have a significant impact on character development, a study was designed which incorporated the listening skills (empathy) training of the Sierra Project (Whitely, 1982) with the Hersey/Blanchard model for situational leadership. College students' (N=39) scores on Kagan's Affective Sensitivity Scale fell within four groups of empathy readiness: R1 (low motivation/low ability), R2 (high motivation/low ability), R3 (high ability/low motivation), and R4 (high ability, high motivation). Subjects were then divided into four listening skills training workshop conditions: S1 (high task/low relationship), S2 (high task/high relationship), S3 (low task/high relationship), and S4 (low task/low relationship). In an effort to monitor the effects of the training on self-esteem, a semantic differential was administered before the workshop began, at the midpoint, and immediately after the workshop. The Affective Sensitivity Scale was readministered after completion of the workshop to measure changes in ability to empathize. The results indicated that high skilled students (R3-R4) who participated in a low structured (S3-S4) treatment did significantly better than high skilled students who participated in the high structured (S1-S2) intervention. Low skilled (R1-R2) students in a high structured (S1-S2) intervention did significantly better than low skilled students in a low structured (S3-S4) intervention. Changes in self-esteem throughout the study indicated the importance of monitoring self-esteem, although at this time results are only speculative. (NRB)