The University of Hawai'i at Manoa Assessment and Curriculum Support Center successfully transformed a four-day, in-person Assessment Leadership Institute (ALI) into an online, four-day program designed to cultivate leaders who facilitate collaborative program learning assessment. We share eight successful strategies, including using the flipped classroom model, role-plays in facilitation simulations, facilitation role-play training prior to the Institute, clear online file structure, dedicated support person, assessment coaches, shared planning scripts, and regular communications. Our observations, participants' self-reflections, and the ALI evaluation provide strong evidence for the effectiveness of the eight strategies, as well as the success of the inaugural online ALI at the University of Hawai'i at Manoa.