This study used a questionnaire to clarify skills and competencies recognized by leaders in community development as well as the factors influencing the acquisition of such skills. Factor analyses were conducted to assess the leaders' mindsets, developmental acceleration factors, leadership skills, and their ability to learn from experience. Using the latent variables extracted from results of factor analyses, a developmental model of the leader in community development was analyzed using covariance structure analysis. The research found that “a proactive stance to learn” influenced “leadership skills” such as “facilitation skills,” “analytical skills,” and “creative skills” through the vehicle of “connections with other people.”