This monograph discusses the implications of digitization and learning organization theory on leadership primarily at the tactical level. Digitization is a term widely used to describe the various technological efforts to improve battlefield operating systems. Learning organization theory is a popular methodology for enhancing the operations of complex organizations. Of particular importance is the positive effect learning organizations have upon the members of the organization. This monograph first examines the capabilities of the tactical digital unit. Next, the monograph depicts the tactics, techniques and procedures of digital units. The Army current doctrinal leadership model is introduced to complete a presentation of what is presently known and available to Army leaders. In response to the rapid and far reaching advances in technology, Army leadership is theorizing a new leadership model. This evolving leadership model has systems thinking, learning organization theory and the effects of digital technology as basic theoretical concepts. Systems thinking is an intellectual paradigm which involves holistic, dynamic processes. Some of the implications of these changes are new, many are not. A discussion of the leadership of Sitting Bull at the Battle of the Little Big Horn illustrates how many learning organization concepts were used long before digitization existed. The monograph analyzes leadership in digitized learning organizations. Army learning organizations will have the following theoretical constructs; personal mastery, mental models, team learning, shared vision and heroic leadership. Systems thinking provides the intellectual energy to bring these concepts to fruition. Finally, this monograph discusses the implications these ideas have for leader development and training. Included are ideas for future digitized learning organization leader training.