The crucial step for organisations which are recruiting Generation Y into their workforce is to understand their perceptions and expectations. This would help organisations emerge with the right strategies to attract and retain the Generation Y cohort. The aim of this paper is to contribute to the body of knowledge base in respect of Generation Y expectations and perceptions on their career choices and its influence on leadership. However, due to lack of academic research on the career expectations and perceptions of Generation Y that deems to be important, popular literature and researches were included in this research (Vieira, 2010). The target sample and population were focused on Generation Y who is undergraduates within the Selangor area. A qualitative method was used in this study to gather perceptions. Although twenty participants were targeted as the sample, the findings and discussions of this research are based on fifteen responses due to the invalidity of the remaining five. The findings generated from the responses were found in line with the theories adopted and explained. Moreover, recommendations for both organisations in Malaysia and future researches are discussed.