In this exploratory qualitative study, we examined African American mentors’ perspectives of what they identify as the needs of their African American undergraduate protégés and the challenges that may impede their protégés’ success. Interviews were conducted with 10 African American mentors who hold STEM PhDs. Data were analyzed using an iterative emergent, thematic coding method and a narrative analysis method as a methodological framework. Findings indicated that some protégés may lack a sense of entitlement or contextualized confidence and may need personalized information and a plan to assist them in navigating academic environments. There are several opportunities for helping undergraduates overcome these challenges, such as mentoring practices focusing on ways to increase protégés’ sense of empowerment and providing personalized information about navigating academia.