This qualitative phenomenological study examines and compares general ideas, perceptions, themes, and understandings related to the development of generation-Y leadership relationships based on virtual socialization. Ten participants holding management roles or seeking leadership advancement in technological, health care, and self-owned businesses were interviewed to assess their perspectives regarding the roles of generation-Y future leaders. Five major themes emerged: (a) clashes between older generation and generation-Y leaders, (b) issues of entitlement, (c) factors related to personality versus those that are generational, (d) variations in decision-making styles, and (e) styles of collaboration at lower levels of organizational hierarchies. Other common themes that emerged from the study, and which are potential topics for future research, include (a) opportunities for generation-Y future leaders to adopt and embrace changes afforded by technological advancements, (b) the need for Generation-Y leaders to establish relationships based on face-to-face interactions, and (c) obstacles to work-place socialization caused by a rapidly evolving teleworking environment, which inhibits development of social interactions and bonds between team members. Results of the present study may prove useful to future generation-Y individuals aspiring to hold leadership roles involving management of a multiple-generation workforce. Organizations may find the outcomes of the study beneficial in their continuing efforts to cultivate and develop generation-Y leaders who will lead and be responsible for high levels of organizational performance and success.