The number of public worldwide mergers, acquisitions, and alliances in 2016 was 49,078 transactions valued at over $4.8 trillion. A survey of executives who selected a restructuring strategy found that 83% of mergers and acquisitions failed to achieve anticipated goals. Poor restructuring success rates may indicate that pre-restructuring emphasis was placed on operational factors rather than human challenges related to the transaction. The purpose of this transcendental phenomenological study was to understand the challenges associated with leadership functions - specifically, leadership, leader-follower relationships, organizational change, and organizational culture - in the context of a technical support restructuring. Twenty participants were interviewed to gain an understanding of their lived experiences associated with leadership and restructuring. Interview audio recordings were transcribed and uploaded into NVivo 11RTM to facilitate data analysis using Moustakas' modified van Kaam method. Research findings indicate (a) empathy, follower development, and competency are valued leadership attributes, (b) quality leader-follower relationships include a personal connection founded on openness, honesty, and trust, (c) leaders should weigh human and operational factors when contemplating organizational restructuring, and (d) organizational culture may provide a competitive advantage if leaders leverage cultural strengths.