As information technology grows in importance and creates industries and disruptions in the growing digital world (Hickman & Akdere, 2018), the practical importance of understanding the impact of leadership development coaching for leaders within information technology becomes critical. As leadership coaching and transformational leadership have both been shown to positively influence leaders in transforming organizations, leadership specifically within the context of an information technology has surfaced as a topic of interest in recent years. The purpose of this qualitative multiple case study with individual interviews was to understand how to create transformational leaders in the information technology environment by exploring instructional content within leadership coaching programs that promotes transformational leadership skills. By performing this research, the study sought to identify leadership skill content that if presented during the coaching process, can promote better transformational leadership among information technology managers and leaders. The theoretical foundation of this study relies on the theory of transformational leadership. The transformational leadership theory identified specific skills to focus on including idealized influence, inspirational motivation, intellectual stimulation, and individual consideration. The results of this analysis presented five themes that emerged from the individual interview content. The themes included activities and assessments, accountability, behavioral skills, and critical conversations. The major implication of this research is that coaching content protocols need to be updated to include the themes of assessment, accountability, enhanced behavioral skills, and regular critical conversations. The results of this study now offer specific instructional content used during the coaching process that is perceived by executive coaches to contribute to the development of transformational leadership behaviors in the information technology context. A key recommendation for future research is to identify specific metrics to assess the extent to which the themes of assessment, accountability, enhanced behavioral skills, and regular critical conversations are utilized in updated coaching content protocols. The results of this research study are of importance because information technology leadership, specifically transformational leadership, is critical to gain competitive advantages in organizations. This new information can be used for the development of transformational leadership behaviors in technology leaders. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]