This study discusses critical strategic factors associated with concerns over implementation of the Fair Labor Standards Act (FLSA) mandate of December 2016. Emergent Human Resources (HR) strategies developed by human resource managers were investigated, as well as how these managers influenced issues directly linked with employee engagement, communication, employee status, and organizational responses. Interviews were facilitated less than four months prior to the mandate’s implementation. Investigators found the FLSA mandate created concerns for human resource managers based on current organizational practices, compensation, and bonus structures, as well as employee morale challenges. Specific findings included a desire for organizational communication concerning changes due to the mandate, but a universal lack of strategic planning or implementation of a process to preserve employee engagement. Further, HR management concerns regarding employee morale and consequent action were investigated, as a change in status from exempt to non-exempt would be perceived as a demotion by most employees. This research finds that the ability to communicate changes with constituents, help manage implementation for HR employees, care for morale and cultural repercussions, and demonstrate fairness in compensation are critical factors to consider for a large-scale change and implementation in HR policy due to sweeping regulatory changes.