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This chapter revisits a foundational question (“what do bosses do?”) to explore how Artificial Intelligence (AI) is reshaping power dynamics in the workplace. Far from neutral tools of optimisation, algorithmic systems increasingly amplify managerial prerogatives, embedding them into automated processes that are difficult to scrutinise, govern or contest. These developments give rise to a paradox: managers and workers are simultaneously augmented and disempowered, caught in systems that intensify control while eroding autonomy. Drawing on legal, organisational and regulatory perspectives, we argue that existing safeguards, ranging from data protection rights to information and consultation, are underenforced and ill-equipped to confront this shift. The chapter critiques the illusion of perfunctory compliance and calls for a structural rethinking of workplace technology governance. We also emphasize a missed opportunity: rather than reinforcing top-down hierarchies, AI systems could be leveraged to democratise the workplace, enhance workers’ agency and enable new models of participation. Doing so, however, requires confronting the socio-legal assumptions that sustain current forms of digital control—and imagining alternative futures where technology serves workers, not just those who manage them.
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