Organizational boards of directors hire senior executive from outside firms during turbulent organizational periods to act as change agents who can bring innovative skills and incorporate distinctive career experiences into a leadership position. Organizational members expect an outsider to incorporate previous experience and initiate novel solutions. The new executives transition into an organizational environment anticipating performing effectively within the first six months of tenure. Fifty-five percent of outsider executives fail and are replaced within the first 18 months, requiring that a new executive begin a transition process to replace the departed executive. The purpose of this qualitative study was to explore how outsider Army Reserve General Officers incorporated their lived leadership experiences and successfully transitioned as executive leaders into new organizations. The study design was a transcendental phenomenology framework as presented by Moustakas (1994), supported by the Kvale and Brinkmann (2009) interview research protocol. The design was nested within the conceptual framework of upper echelons theory (Finkelstein et al., 2009; Hambrick & Mason, 1984). Three leadership implications emerged from the data provided by 17 sample members. First, successful transition was a self-serve activity in which feedback from superiors was accepted as no news is good news. Second, the 12-18 month tenures are at odds with long-term organizational leader stability. Third, establishing niche activities is useful to forming leadership credibility.