Community intergenerational mentorship offers an opportunity to address older adults’ social isolation while providing valuable one-on-one or small group learning experiences for elementary school students. Current organizations that support this kind of engagement focus on in-person visits that place the burden of logistics and transportation on the older adult. However, as older adults become less independent while aging, coming to schools in person becomes more challenging. We present a qualitative analysis of current intergenerational mentorship practices to understand opportunities for technology to expand access to this experience. We highlight elements critical for building successful mentorship: the importance of relationship building between older adults and children during mentoring activities, the skills mentors acquired to carry out mentoring activities, and support needed from teachers and schools. We contribute a rich description of current intergenerational mentorship practices and provide insights for opportunities for novel HCI technologies in this context.