The teacher shortage will be a major hurdle for school leaders over the next several years with declining enrollments in teacher preparatory programs and many teachers changing professions in their first five years. The "2021 Illinois Educator Shortage Survey," authored by Shereen Oca Beilstein and Tom Withee, and sponsored by several organizations including the Illinois Workforce and Education Collaborative (IWERC), Goshen Education Consulting, Illinois Association of Regional School Superintendents (IARSS), and Center for the Study of Education Policy (CSEP), collected information from 78% of the public schools in Illinois. More than 85% of the schools that responded stated that they were currently feeling the impacts of the teacher shortage. Many educational leaders and school boards believe that low salary, reduced pension, or lack of community support are factors pushing teachers to another district or out of the profession. Teachers, however, cited quality of leadership as the most important factor when choosing to stay in their current district, move to another district, or leave the profession entirely. The goal of this dissertation study was to investigate which characteristics or actions of leaders indicate high quality and how identified leadership skills can be improved to combat the teacher shortage. This study explored which leadership qualities teachers care about most. Equipped with this information, school leaders can focus their own professional growth to improve in the areas that impact retention most. The trickle effect of improving quality of leadership may positively impact the number of teachers willing to stay in the profession and even encourage more students to consider teaching as a viable career option. [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.]