Creating a dynamic educational community takes collaboration and accountability from ALL constituents. Current research on leaders sets the foundation for recognizing the need for organizations to develop wellness initiatives and enhance research. In today's transient work world, wellness initiatives may aid in retention. Targeting the emotional wellness of administrators is essential for adopting supports that aid in job fulfillment. Educational administrators impact the overall functions of the education community. This study examines and compares the leadership skills of public school administrators and factors that contribute to job satisfaction. Analysis of published studies revealed the need for further research on diverse levels of educational leadership aligned with characteristics and components of job satisfaction. Similar studies identify leaders' roles and account for factors that aid in elements of job satisfaction but miss leaders' skills. Pennsylvania superintendents and assistant superintendents participated in the study. The Skills Inventory (Northouse, 2019), the Minnesota Satisfaction Questionnaire short-form (Weiss et al., 1967), and demographic questions informed the study. The study sought to understand if there is a significant difference between leadership skills and factors related to job satisfaction among Pennsylvania public school administrators. Results indicate that school administrators differ in leadership skills and are satisfied. The study aided in the knowledge of research identifying the leadership skills of superintendents and assistant superintendents and job satisfaction elements. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]