Community college presidents and senior leadership recently gathered for a deep dive into two hot-button issues for two-year colleges — the future of distance learning and artificial intelligence (AI). Online classes have been disrupting enrollments for more than 25 years and continue to be the primary source for enrollment growth. This modality of instruction offers the best instructional method to serve the growing number of active adult learners in a rapidly changing workplace, as well as dual-credit enrollments for high school students. College leadership needs to better understand how to support and expand online courses and degrees. AI, on the other hand, presents a different set of challenges and opportunities for college leadership. In the two years since Generative AI launched, corresponding emerging issues include ethical use, privacy, access and cost. Leadership needs to learn how to manage, prioritize and finance this new technology while reassuring faculty that academic integrity will be maintained.