This paper investigates reasoned risk-taking in decision-making by school principals using a methodology that combines sequential use of psychometric and traditional measurement techniques. Risk-taking is defined as when decisions are made that are not compliant with the regulatory framework, the primary governance mechanism for public schools in Western Australia. This creates a dilemma for principals who need to be able to respond to the locally identified needs within a school, and simultaneously comply with all State and Commonwealth departmental requirements. A theoretical model was developed and data collected through the survey of a stratified random sample of principals in 253 Western Australian government schools. Rasch measurement was used to create a measurement scale. The hypotheses were tested used partial least squares structural equation modelling. This analysis provides evidence of the effect of governance structures, characteristics of schools and principals that influence decision-making in schools.