This multiple case study utilizes interviewing, shadowing, classroom observation and document review to investigate holistic educators' perspectives on essential outcomes of holistic education, how desired outcomes are supported, perceived self-efficacy and perceived likelihood of success. Participants include kindergarten and upper elementary teachers in Montessori, Waldorf and Homeschools. Expectancy Theory (Vroom, 1964) and a proposed Holistic Educational Theory were used along with layers of iterative analysis to ground and frame the study. Participants reported that providing support for various aspects of students' interpersonal, intrapersonal and transpersonal development were top priorities. They describe utilizing a variety of methods for providing support for development in these areas and reported feeling both high likelihoods of success and high levels of self-efficacy in each area.