The trajectory of colon and rectal surgery residency program director (PD) career paths has not been well described, leaving those who aspire for the position with minimal guidance. The goal of this study is to characterize their career paths in the United States. By understanding their experiences, the path to train and educate the next generation of colon and rectal surgeons as a PD will be better illuminated. This study was an anonymous, cross-sectional survey of all junior and senior colon and rectal surgery residency PDs in the United States during April and May of 2022. PDs were divided into junior and senior PDs. Results were compared using 2-sided independent t-tests and Kruskall-Wallis tests. Of 65 colon and rectal surgery PDs, 48% (31/65) completed the survey which encompassed demographics, leadership, education, research, and time utilization. Participants were primarily white and male, although increased female representation was identified among the junior PDs (50%). Junior PDs were also more likely to hold associate or assistant professor positions at time of appointment (p = 0.01) and a majority of all PDs (64%) previously or currently held a leadership position in a national or regional surgical association. When appointed, senior PDs reported increased teaching time. This multi-institutional analysis of colon and rectal surgery residency PDs identified a trend towards equal gender representation and diversity amongst upcoming junior PDs. All respondents were appointed to PD from within the institution. Other key experiences included previous leadership roles and associate or assistant professor positions at time of appointment. While it is impossible to create a single recommended template for every aspiring colon and rectal surgery educator to advance to a PD position, this study provides guideposts along that career path.