Informed by structuration theory, this study demonstrates how organizational structures – flexibility policies related to worker teleworking – shape communication flows of membership negotiation and activity coordination. Interviews with 53 employees from 2 large Finnish firms revealed that in the organization in which teleworking was permitted workers agentively structured their workdays to use the policy to serve both individual and organizational needs and easily adapted to coworkers’ teleworking. By contrast, nearly the opposite was found in the organization that allowed teleworking only by exception; in fact, most did not value teleworking or desire additional flexibility. Through negative discourses about telework, an organizational culture that did not support flexible work was reproduced, maintaining the expectation and effect that organizational activity occurred only at the office. We conclude with practical insights concerning how differences in policies can enable co-creation of differing employee task performance and workplace relationships, and most especially employee views about work–life boundary management.