This study builds upon Deci and Ryan’s (1985) Self-Determination Theory (SDT) which states that humans must meet three basic psychological needs for optimal well-being: autonomy, competence, and relatedness. The purpose of this qualitative study was to explore trends in principals’ experiences in the areas of autonomy, competence, and relatedness. Research questions include: How do public school principals score in the areas of autonomy, competence, and relatedness? Do principals’ responses vary depending on whether they have been formally coached or not? Do responses vary depending on whether principals are working in Program Improvement (PI) Schools or not? Finally, to what do principals attribute their scores in the areas of autonomy, competence, and relatedness? A 27-item questionnaire based on the Self-Determination at Work scale as developed by Deci and Ryan (1989) was given to 199 eligible principal candidates followed by contact by phone and/or email to arrange interviews. The second phase included eighteen one-on-one interviews with randomly selected participants from within each of four categories: (1) coached/PI, (2) coached/non-PI, (3) not coached/PI, (4) not coached/non-PI, as determined by responses on the questionnaire. All responses were voluntary and participants had the option to decline to respond to items on the questionnaire. Participants were K-12 public school male and female principals from schools within Ventura County. Principals represented a variety of experience levels, and a variety of sites. Elementary, middle, junior high and high schools were represented in the study, including schools that were in Program Improvement and those that were not.