This article is the second in a pair examining my experience leading 30 educators through professional development training on the "SPEAK Young Women's Vocal Empowerment Curriculum" in Guatemala. To guide my examination, I have looked to the question, "What does it take to train non-teaching artists in the skills needed to lead a curriculum traditionally taught by teaching artists?" This article seeks to answer this question through the lens of our "Voz Empoderada Diplomado" or "Vocal Empowerment Certificate Program," which took place in 2019. In this second installment, I outline the structure of the Diplomado, explore the challenges we faced, and share our lessons learned for training educators in teaching artists' approaches in the future. [For part one, "Certified Teaching Artist? Using Professional Development to Train Mentors, Teachers, and Community Workers in a Teaching Artist's Approach," see EJ1292880.]