It is widely accepted that mentorship between people of similar backgrounds and slightly different ages is a mutually beneficial partnership (e.g., Angelique, Kyle, & Taylor, 2002; Yomtov, 2017). Mentoring relationships exist in many forms across the education spectrum, from middle school students interacting with their younger peers to the popular “Big-Little system” adopted by fraternity and sorority groups in U.S. colleges and universities, and beyond educational settings throughout the working world. However, one place where mentoring has received relatively less attention, from researchers as well as from practitioners, is in undergraduate student leadership-focused organizations at the college level.