Agile and User-centered design processes have been reported to frequently putting contradictory demands on people working within these methodological frameworks. The current research addresses this point by focussing on the crucial relationship between software developer and designer. An online survey, a contextual inquiry, and a diary study were employed with 107 developers and designers in a large media organization to determine the factors for success in agile development cycles. The results from the survey show that while developers and designers have similar levels of satisfaction with agile processes, there are differences in the factors predicting those ratings. Developers are happier with the wider teamwork but want more access to and close collaboration with designers, while the latters? concern was the quality of the wider teamwork. Additional contextual inquiries and a diary study with pairs of designers and developers reflected the survey findings that close cooperation (and proximity) was essential for improving communication, reducing inefficiencies, and avoiding suboptimal products being released. However, organizational processes, the setup of the work environment, and managerial traditions meant that this close collaboration and localized decision-making was found difficult to maintain. Results from the survey, the contextual inquiry, and the diary study found six factors for success from collaborations emerged.