The emerging popularity of Web 2.0 technologies for organizing people and influencing them through reciprocal collaboration and communication has fostered a new leadership paradigm within organizations, that of the technology-driven leader. With recent political campaigns having embraced Web 2.0 technologies with considerable impact, businesses have started exploring its potential in redefining corporate leadership, bypassing established structural hierarchies to directly reach out to employees and engage them in creative dialogue and innovative thinking and to calibrate messaging in line with organizational objectives. Drawing upon the Unified Theory of Acceptance and Use of Technology (UTAUT), this initial study examines the facilitating conditions for fostering organizational leadership through adoption of Web 2.0 technologies. The personality traits that can lead to efficient technology-driven leadership as well as the comparative efficacy of Web 2.0 technologies in fostering leadership perceptions among employees will also be examined.