This paper examines how generational divides and technological transformation influence communication within the workplace, using The Knockoff by Lucy Sykes and Jo Piazza as a primary narrative lens. By applying Human Relations Theory and Media Richness Theory, the study explores how communication practices differ between digital natives and traditional media professionals, often leading to misunderstandings, emotional disconnect, and cultural fragmentation in organizations. The novel reflects the real-world anxieties surrounding workplace modernization, demonstrating the tensions between efficiency and empathy in digital communication. The analysis shows how evolving media formats, from print to app, or phone call to tweet, redefine workplace relationships and roles. It concludes by emphasizing the need for balanced communication strategies that preserve human connection in digitally transforming workplaces.