In today’s workplace, supervisors often communicate with direct reports using technology that could influence the perceived relationship employees have with their managers. The purpose of this convergent mixed methods study was to describe the perception of how media richness, when using technology to communicate, influences the relationship direct reports have with their supervisors. To address the research question, a survey was used with a sample of 100 direct reports who frequently receive communication from their supervisors in different technology formats. The results from the study suggest that technology media influences the perceived relationship between direct reports and their supervisors. According to the results of this study, technology media may be especially helpful in bolstering the availability of supervisors, which may positively influence other elements of the supervisory relationship. The results further suggest that it may be important for all leaders to choose technology media that is personalized and preferred by the employee while also using the most effective media for the type of message. Finally, leaders should understand the concerns that employees may have around privacy and overuse of technology media.