While there is an abundance of empirically based information on the broad subject of executive leadership and executive leader development, opportunity for further research is driven by complexity of the executive’s world and the related need to function at high levels of learning agility. In fact, learning agility has been identified by Korn/ Ferry (Korn/Ferry, 2011) as the single most important predictor of executive success. This study seeks to explore non-traditional forms of executive leader development based on an integrated theoretical lens, including learning and executive development theories as they relate to learning agility. Executive Coaching is of primary interest as an executive development theory, with a diagnostic element designed to provide insight about development issues, particularly those around leadership pipeline cross points. The Competing Values Framework, as applied here for individual executive growth and development constructs, offers an additional theoretical lens as well as a structure for practical application. Using an engaged scholarship approach through Action Research, this is explored with a focus on executive development options that go beyond traditional leadership training models, and with research, insights analyzed through the CVF assessment and structured interviews. Among the findings are insights which confirm the learning agility construct claims that it is a key predictor to executive success as executives traverse career transitions. More specifically, the insights which proceed from this study also support the reasons that self-discovery learning interventions impact learning agility for senior executives. They include: The Participants in this study demonstrated Learning Agility Development as defined for this research, providing evidence that Learning Agility can be developed Executive Coaching and Related Self-Discovery Constructs contribute more to Learning Agility Executive Development when the executive coach offers a fluid approach which includes significant engagement and mutual dialog as well as inquiry. Learning Agility Development is related to one’s ability to manage Competing Values, especially Competing Values that are unique to the individual. Individual Awareness, its connection to reflexivity, and the movement of tacit knowledge to explicit knowledge is a key finding related to senior executive learning agility development. A Systems Approach to Learning Agility Executive Development which includes a systemic framework, a defined process/structure, and individual customization is indicated for senior level executives. The study offers extensions to existing theories as well as a practical theory-and-findings-based executive development methodology.