Researchers have documented that high expectations do not always result in higher achievement, but the reason for varying results has not been clearly understood. This correlational study was done to find out if the degree of presence of principal leadership characteristics can predict when high expectations are effective and when they are not. Expectancy and transformational leadership theories provided the framework for identifying 9 principal leadership characteristics that might influence student scores on Colorado statewide testing. Existing student testing data were considered the dependent variable, while survey data on the leadership behaviors of Colorado middle school principals were used for the independent variables. Data were tested using a correlational regression analysis. The transformational leadership independent variables of beneficial modeling, inspirational motivation, systems thinking, individualized consideration, and empowerment were each found to be significantly related to statewide test scores at the .05 level. The high expectations variable was not found to be significantly related to test scores by itself but was found to be significant (p = .016) when transformational leadership characteristics were also high. Principals who were perceived to provide teachers with the environment they needed to facilitate student achievement were correlated with higher test scores. Implications for social change include public policy makers' support for transformational educational leadership as a part of providing teachers with what they need in order to meet high expectations.