The use of facilitators to engage visitors in conversations at collections-based institutions has the potential to greatly impact and deepen visitor experience. The job requires the development of complex skills across specific strands of study. In this article, we share details on the strands of study in the training of youth floor facilitators from diverse backgrounds for work in a collections-based museum. This training program has been developed over several years. In this article, we review lessons learned, discuss issues we continue to grapple with, and recommend opportunities for further research for practitioners and researchers.