Using the qualitative approach, the study sought to explore the challenges of managing millennials in the hospitality industry, with a focus on Simbisa Brands Limited. An in-depth interview guide and documentary review were used to collect data, with a sample size of twelve participants. According to the findings of the study, Simbisa Brands' management faces insubordination challenges when dealing with millennials within their organization. It was also observed that excessive social media use by young employees, economic challenges, and overburdened workloads all have an impact on their productivity. Recommendations were that Simbisa Brands management would deal with insubordination by seeking the services of an employment law expert for quick and impartial advice. Importantly, staying organized can help an organization handle a heavy workload by streamlining the process of finding information and making decisions. The organization can also implement a planner system that displays its workload at a glance. Researchers also recommend that Simbisa Brands implement structural reforms that increase work autonomy and flexibility for its millennial employees. Future research could look at private and public sector organizations and use a mixed-method research approach to overcome the limitations of using only one research strategy.