Change is a constant theme in organizations, and policy implementation or change implemented from the top-down can have its challenges. This project aimed to identify and assess current work strategies used to support changes from legislative policy implementation and develop communication interventions to navigate its dilemmas. Through a study of change implementation at a government agency, the researcher identified five dilemmas that centered around managing feedback between employees, conflicting perspectives between stakeholders, and gaps in staff resources. Findings suggested that employees at this agency developed a set of five strategies used to manage the problems and dilemmas brought on by policy implementation. Practical implications from this study indicate organizations should assess whether similar dilemmas exist during their change initiatives. Furthermore, collaborative technologies were pivotal to supporting remote work operations and completing time-sensitive work.