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This research employed a one-shot case study design to examine the relationship between the dependent variable, acquisition of the initial elementary principalship position, and several independent variables. Independent variables included the presence or lack of professional mentoring; the type of mentoring received by proteges; the gender of the mentor and protege; the perceived impact of mentoring, dependent upon the method of establishment of the relationship; and the career path of respondents. Additionally, the study examined the relationship between having been a protege and the tendency to mentor others. To examine these relationships, the Mentoring and the Elementary Principalship Survey was designed. The choice of survey items was based on an extensive search of the literature on mentoring, career paths, and gender as these relate to the acquisition of educational leadership positions. Of the 600 surveys sent to randomly selected elementary administrators, 316 respondents from 49 states returned the survey, with 51.9% of the respondents being females and 48.1% males. Data were analyzed using t tests, Analyses of Variance, frequency distributions, cross tabulations and chi square tests, and post hoc analyses where appropriate, and revealed the following findings. There was found to be no significant interaction between acquisition of the initial elementary principalship position and the different types of mentoring, specifically Encourager, Role Model, or Political mentoring, or mentor gender. The data indicated a significantly shorter time to acquisition of the initial elementary principalship for males, as opposed to females, in all career paths. No significant difference was found to exist between acquisition time of males in the Teacher to Principal path and the Teacher to Coach/Physical Education/Special Education path; significant differences were found to exist for males in the Teacher to Counselor/Supervisor/Assistant Principal path. A highly significant relationship was found to exist between one's having received mentoring and the tendency to mentor others. However, there was no statistically significant difference between the protege's perceived value of mentoring and the method in which the relationship was established.