This study investigates the unintended consequences of attempts to engineer serendipity in modern workplaces during the remote and hybrid era. By examining the interplay between employee agency, autonomy, and organizational power dynamics, we identify seven critical mechanisms that reveal how the interplay of employee agency, autonomy, and organizational power dynamics impacts the conditions under which serendipity emerges—or fails to emerge—as a process of individual and organizational value-making. At the individual level, we reveal how agency and autonomy influence serendipitous outcomes, while leadership and power structures, impact collective serendipity. Our findings highlight that while alignment enables serendipity as a collective phenomenon, misalignment drives employees toward individualistic value-making, disengagement, resistance, and diminished organizational outcomes. Our paper underscores the fragility of (engineered) serendipity, demonstrating how misaligned strategies can undermine its intended benefits. By offering theoretical insights into the conditions under which serendipity thrives or falters, we contribute to the literatures on remote/hybrid work and serendipity, providing a framework for fostering collective serendipity.
