Inspired by the perceived success of the Social Media, an increasing number of companies have started to introduce social-media-like software systems (Enterprise Collaboration Systems). In order to study the issues and challenges that such introduction projects bring about, we selected a sample of companies and conducted interviews with managers, IT experts and users. The analysis of the responses shows that the experiences among the companies and among people in the same roles in these companies are very similar. All case companies used an approach that could be described as experiential, or laissez-faire, meaning that they installed the system and invited their staff to use it – without clear instructions or management controls. This led to a certain degree of insecurity and the adoption rate was lower than expected. We argue that the laissez-faire approach did not stimulate (the full potential of) project success. The findings also show that the introduction of social software brings about cultural rather than technical challenges. These cultural challenges can be anticipated and should be managed ex ante, not ad hoc.