The study explores the organizational characteristics of strategic planning, succession planning and career management and the processes impact on the hiring location of academic leaders from within the college, external to the college but within the system, and external to the system. The study was conducted in the 16 college Wisconsin Technical College System. The population included the chief academic officers, academic vice presidents or provosts, deans, and associate or assistant deans. An online quantitative survey was distributed to the population of 236 individuals with a 67 percent return rate. The study results indicate a direct relationship between the maturity of strategic planning and the maturity of succession planning. The study also explores leadership development experiences offered by two-year technical colleges and respondent satisfaction and value of the leadership development experiences. The study finds no relationship between organizational characteristics of strategic planning, succession planning and career management and the location of academic-leadership hires. The results of this study establish a link between organizational-strategic planning, succession planning and administrative-career management within two-year technical colleges. These data further identify relationships between the academic administrators perceptions of the elements of strategic planning, succession planning and career management used within his or her respective organization. In addition, the study also explores the satisfaction of leadership experiences and identifies the point in career progression when the learning experience reflects the highest satisfaction. [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.]