A qualitative, grounded theory research was conducted to explore and deepen the understanding of how middle and low level managers can initialize and manage information technology (IT) outsourcing projects. The study involved 17 managers and leaders working in Ukraine in offshore software development companies. A grounded theory was utilized to analyze data from participants to identify the interrelationship among seven core categories including: (a) project communication, (b) employee training, (c) flexible organization, (d) strategic communication, (e) team unit, (f) transparent management, and (g) vendor adaptability. A combination of the categories formed the foundation of a new theory on the role of natural systematic approaches with social networking technologies in effective software outsourcing to Ukraine.