Diversity has entered the leadership arena, as it has all other aspects of life. As we prepare leaders to lead in a more diverse world and train managers in the skills needed to succeed in a competitive society, we must understand what managers’ activities consist of and how leadership styles differ. The purpose of this qualitative study was to investigate the activities of Chief Executive Officers in businesses from a variety of sectors, document differences in male and female leadership styles, and compare these findings with previous studies. Data were collected through observation and creative interviews with three female and three male CEOs, one of which was a minority. The CEOs had been employed in his or her position for at least two years, and the organizations were diverse, successful, and well-known. Observation notes, dialogue and creative interviews were analyzed using Glaser and Strauss’s (1967) constant comparative method. Variety, brevity, and fragmentation were found in the activities of a contemporary manager, and attitudes toward scheduled breaks, interruptions, outside activities, outside businesses, reflection, communication, technology, and identity were found to be similar between male and female leaders. The CEOs tended to value the importance of breaks, have tolerance for interruptions, participate in outside activities, and establish outside business relationships. Also, they tended to value reflection, have informal and formal ways of sharing information with employees, have been impacted for the better by technology, and have a multi-faceted identity. Additional qualitative and quantitative research was recommended to further explore how studies can help prepare leaders by understanding the activities and leadership styles of contemporary managers.