There has been a diminishing pool of suitable candidates for school leadership positions in the Australian Catholic education sector. Currently, there are three major generational cohorts of teachers in schools, including Baby Boomers, Gen-Xers and Millennials. Research in corporate and government sectors has found that these cohorts have distinctive traits and characteristics that shape their approach and expectations to the workplace. Significant research has been undertaken into the declining number of teachers willing to undertake middle and senior school leadership roles. But there is limited research into the factors behind this numerical decline. One area to consider is whether generational differences exist amongst teachers, and how they may be influencing school leadership shortages. This multi-generational workforce teaching and leading alongside each other simultaneously is a new challenge for education officials and schools who are facing leadership succession shortages in both the quality and quantity of aspiring candidates. The main focus of this research project is to explore the differing generational perceptions of each cohort in their perceptions towards workplace behaviours, as well as whether their differing attitudes toward traditional school leadership processes are contributing to these leadership succession issues. This research has sought to identify generational differences in perceptions and expectations of teachers and school leaders towards their workplace and leadership succession culture; and, evaluate the extent to which these differences can provide insight into leadership succession issues faced by the Catholic education sector. This quantitative, quasi-experimental study has a positivist theoretical framework, and was explored through the lens of Generational Cohort Theory (GCT). It utilised the Generational Perceptions of School Leadership (GPSLi) Instrument to elicit any differences amongst the three generational cohorts. Five subscale variables of Motivation, Work Ethic, Professional Feedback, Leadership Development Culture, School Hierarchy were framed under the construct of Workplace Perceptions; and, four subscale variables of Intentional Leadership Succession Planning, Culture of Mentoring Leaders, Leadership Styles and Expectations, and Awareness of, and Catering of Generational Differences under the construct of Leadership Perceptions. Data analysis was conducted through Kruskal-Wallis H testing, followed by Mann- Whitney T testing to locate and explore identified differences. Mannheim (1972) and Strauss and Howe’s GCT (Strauss & Howe, 1991) was chosen as the guiding framework for discussion and analysis as it holds that each generational cohort is shaped by social and historical events that influence their perceptions, traits, expectations and preferences. The present study identified differences in two subscales of Motivation and School Hierarchy under the Workplace Perceptions construct; and, three subscales of Intentional Leadership Succession Planning, Culture of Mentoring Leaders, and, Leadership Styles and Expectationsunder the Leadership Perceptions construct. These results support previous research from other sectors that the generational cohorts have different motivations, perceptions, preferences, and expectations in their attitudes towards workplace behaviours and leadership culture. Interpretations of the findings also infer that the differences of the generational cohorts can be utilised for both further research, as well as provide opportunities for school leaders to potentially adapt and change existing recruitment, development and retention strategies for both existing and aspiring leaders