This study examined the effectiveness of a program developed for middle-aged and elderly workers to improve their empathy skills. The results of the program for 16 participants in their 40s and 50s belonging to companies and organizations showed significantly higher levels of satisfaction and goal attainment. The willingness to demonstrate empathy was evaluated as a measure of the effectiveness of the program at the end of the program, with the aim of putting it into practice in the workplace after the program. Although no significant difference could be confirmed by comparing the pre- and post-program scores, a correlation analysis centered on the item "self-efficacy to demonstrate empathy," which itself improved the score, was conducted to examine the internal characteristics of the participants and sessions that seemed to be highly related to the effectiveness of the program.