The process of implementing developmental evaluation for The Rockefeller Foundation’s youth digital employment initiative yielded some valuable lessons which could be of benefit to the evaluation community, particularly evaluation practitioners and managers. This paper presents those lessons, including the challenges the evaluation team faced, the solutions it brokered, and the insights to be applied in the future. It is the Foundation’s hope that this report will provide answers to questions about when and how to use developmental evaluation, and encourage evaluators to adopt it when appropriate.