Research has shown that the relationships employees have with their supervisors or managers is one element that may influence employee engagement and retention. As part of building a positive relationship, communication may be a key factor of influence. In today’s workplace, supervisors often use technology to communicate with direct reports. With the increasing use of technology to communicate, there could be influences on the perceived relationship employees have with their managers, with various media having different levels of impact. The purpose of this convergent mixed methods study was to determine which technology media are perceived to be most and least effective in fostering a positive relationship between direct reports and their supervisors. The full range leadership model (Bass & Avolio, 1994) provides a theoretical framework for this study and describes various leadership styles and their effectiveness in motivating employees. Specifically, within the full range leadership model, the transformational leadership style may be an effective approach toward engaging employees that could also be influenced by technology media. Our findings indicate that 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 a technology medium that is personalized and preferred by the employee while also using the most effective medium for the type of message. Finally, leaders should understand the concerns that employees may have around privacy and the overuse of technology media.