This article proposes experimentation as a framework for understanding actor agency in the changing regulation of work and employment. This involves contrasting institutional change with organisational and institutional experimentation approaches in order to understand how, in the context of uncertainty, actors in the world of work experiment with new ways of organising and seek to institutionalise them into new understandings, norms and rules. The article describes the fault lines of disruption that are generating a vast range of experiments in the world of work. These fault lines invite resilient responses and the development of collective capabilities at two levels: first, organisational experimentation, where social actors seek to modify or renew their organisations, networks and alliances and reflect on, assess and learn from their experiments; second, institutional experimentation, where these responses are scaled up and institutionalised over time through more general understandings, norms and rules. A key challenge for comparative research and strategising is to find the appropriate institutional conditions that will facilitate and enable organisational experiments, whilst overcoming constraining institutional conditions. This challenge is illustrated through the examples of co-working and the development of new forms of collective representation.