Researchers have found that a positive correlation exists between information technology (IT) flexibility, IT effectiveness, and strategic alignment in organizations. It has been determined that within inflexible IT environments maintainability is reduced and key business factors become at risk. An IT flexibility measurement matrix was developed to assess IT flexibility however leadership characteristics were not identified for measurement with that model. Determining the leadership characteristics needed for IT flexibility was the purpose of this multiple case study. Leveraging the empowerment, situational leadership, IT-business equilibrium, and complexity change theories, the research questions were focused on the leadership characteristics exhibited by organizational and project team leadership. A purposeful sample of 20 IT nonmanagers participated in in-depth interviews and provided insights into leadership characteristics that were observed and practiced in flexible IT environments. Using deductive a priori coding and inductive data analysis, communication was identified as the leadership characteristic required by both organizational and team leadership. Other emergent leadership characteristics were having a vision, managing change, and servant leadership. The implications for positive social change are for organizations to use the results to develop leaders and teams to successfully manage flexible IT environments, enabling improved IT-business alignment. Academic institutions can provide structured training and cooperative education programs, partnering with IT organizations to develop and retain top IT talent. In addition, individuals can build knowledge and gain experience in these areas to strengthen personal and professional skills, thus increasing career potential.