Coworking spaces (CWS) and the associated practice of coworking, have emerged in numerous forms and various urban contexts to critically challenge traditional concepts of the workplace and location of creative work, while simultaneously confronting the way in which creative workers interact with and relate to each other as well as with space and to place. Heralded as a solution to increasingly atomised work patterns, CWS are imagined and presented as spaces of serendipitous encounter, spontaneous exchange and collaboration. Nonetheless, little is known about how coworking positively supports workers and how coworking relates to wider urban transformation processes has been largely un-researched. This paper contributes to a critical discussion through empirical analysis of a project aimed at establishing new creative CWS in city-centre locations across SE England. The study adopts a novel approach using Q-methodology. Motivations for coworking and benefits (or dis-benefits) of co-location are assessed, as is the extent to which coworking facilitates interactional effects and wider neighbourhood interactions. In particular, the role of the CWS manager as “mediator” is explored. Coworker benefits relate primarily to peer-interaction and support rather than formal collaboration. While CWS managers play a key connecting role, also ensuring coworker complementarity and compatibility, the coworker profile (motivations, needs, experiences) ultimately influences outcomes. The study cautions against the use of CWS as “quick fix” urban renewal tools, with little indication that the benefits of coworking reach beyond immediate members or that linkages are easily established between coworkers and local (resident or business) communities.