Abstract: A system and method of optimizing employee communication to improve workplace engagement and retention is a data collection, storage, and processing software program that can improve employee retention and job performance by employing each employee with an accessible, personalized chatbot assistant. The chatbot assistant directly interacts with an employee to determine optimal solutions based on the employee's implicit or explicit needs and aspirations. The chatbot assistant further makes suggestions based on interactions with the employee and automatically implements any solutions chosen by the employee. Conversational data is collected and used to calculate optimal interactions with each employee. Such data is also valuable in calculating and responding to employee sentiment, thereby improving retention by responding to those calculated emotional scores.