A SIPA workshop team consisting of eight students worked with the Inter-American Development Bank’s Citizen Services Division to review and create six case studies examining how private sector organizations manage the human side of large-scale digital transformations and to formulate best-practices for Latin American and Caribbean governments to use to handle similar large-scale digital transformations. Based on a thorough literature review and interviews with experts and employees of private sector organizations from Belgium, Japan and Singapore, the team provided a series of best-practices and recommendations. These included prioritizing significant investment into its employees, conducting retraining when undergoing automation, incrementally implementing new technologies, and involving workers in the decision-making process through union participation or work councils.