Can meaningful connections between academics, consultants, and practitioners of workplace democracy be created to bring about critically inspired change? This article presents an exploration of our experiment in producing a practical and engaged form of Critical Management Studies (CMS) through a case study of a 2-day event. The event brought together academics, consultants, and practitioners of workplace democracy to examine the possibilities and challenges of creating meaningful connections between these groups. It served as a platform for investigating and reflecting on the efforts made to bridge the gap between academia and practice in CMS. Drawing on pre-event documents, recordings of the event and interviews with participants after the event, we provide an account of academics out of their comfort zone struggling to feel authentic and useful; suspicion and uneasiness between groups leading to inter and intra group struggles; and lingering difficulties around power and control. Our event suggests that CMS scholars seeking more practical engagement should pursue a: (i) deliberative research perspective of co-production alongside multiple stakeholders (academics, consultants, and practitioners) to practically seek to bring about change; (ii) democratization of the research process so that the democratic intentions of the research outcomes are built into the research process; (iii) fluid research position breaking down and blurring of boundaries between academics and practitioners to increase the possibilities for creating meaningful connections.