The purposes of this study were to (a) identify themes in the literature with respect to critical skills of the Chief Student Affairs Officer (CSAO), (b) assess the perceptions of CSAOs about the importance of each of the critical skills identified, (c) assess the perceptions of CSAOs about the individual philosophies guiding their day-to-day work, and (d) determine if there are differences in the importance CSAOs placed on critical skills based on their guiding philosophy. The CSAOs at NASPA member institutions in Regions II and III were surveyed using the Chief Student Affairs Officer Critical Skills Inventory developed by the researcher. Four hundred and ninety-one NASPA Voting Delegates (CSAOs) were mailed the survey and 256 returned the survey for a 52% response rate. CSAOs were asked to rate the importance of 69 critical skills and rank the three guiding philosophies (student services, student development, student learning) in order of importance both in their day-to-day work and in an ideal setting. Responses included 102 women (40%) and 152 men (60%); 208 (82%) Caucasian CSAOs and 46 (18%) CSAOs of Color; 142 (55%) CSAOs were in their first five years in their current position; 165 CSAOs (65%) held only one position; and 173 (68%) had earned a doctorate. For their day-to-day work, CSAOs were evenly divided as to their guiding philosophy with 37% choosing student services, 39% choosing student learning, and 24% choosing student development. For an ideal environment, 12% of CSAOs selected student services, 56% chose student learning, and 32% chose student development. When examining the importance placed on critical skills with respect to gender, ethnicity, years of professional experience at the time of attaining the first CSAO position, tenure in position, field of degree, reporting category (whether they report to the president or provost), Carnegie classification of institution, and guiding philosophy, many responses were statistically significant. The skill rated the most important was "maintain integrity in decision making." The skill rated the lowest was "hold office in professional associations."