The central research problem is the insufficient supply of teachers opting for promotion to middle-level leadership positions in Singapore secondary schools, where about 66% are filled. This shortage limits the effectiveness of school management and reduces the flow of leaders aspiring to vice-principalship/ principalship. The study generates a model by addressing two research questions:\ud (1) What influences affect secondary school teachers’ decision-making as to whether to aspire to middle-level school leadership?\ud (2) How do these influences affect the career aspirations of Singaporean secondary school teachers?\ud Using the interpretivist paradigm, case study approach, and content analysis methodology, semi-structured interviews were conducted with a stratified sample of 20 participants. The investigation sought teachers’ perceptions of middle-level school leadership (compared to teaching) and their career aspirations, and identified the associative influences on their career decision-making. Such influences can be grouped into the categories of personal, socialisation and environmental influences, with each linked to two qualitatively different categories: teaching and leadership influences.\ud Teachers’ career decision making is affected by ‘personal’ influences, resulting from innate attributes and pre-service experiences. Interactions with friends, family and significant others also give rise to ‘socialisation’ influences.\ud ‘Environmental’ influences result from home and school environments. Teachers at different career stages (beginning teachers (0-3 years), more mature teachers (3-5 years), more senior teachers (beyond 5 years)) are more susceptible to particular influences; for example beginning teachers prefer honing pedagogical skills than doing administrative tasks. Teachers progress through these career stages and experience the influences identified. These influences affect individuals differently, for example additional remuneration may be less attractive for more established senior teachers compared to beginning teachers.\ud Teachers’ decision-making processes regarding leadership aspirations lie at the heart of the Model of Selective Appeal, so named because particular influences on whether to opt for leadership selectively appeal, or otherwise, to individual teachers
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