Powerfully driven by the work practices of consulting firms, the presentation software Microsoft PowerPoint is increasingly used on all levels of business and educational communication. Nevertheless, slideware ranks among the least explored media in communication studies. This study investigates the role of PowerPoint in organizational communication, particularly in terms of a functional dilemma between its application for documentation as opposed to presentation purposes. The theoretical part of the analysis combines insights from both organizational communication studies (J. R. Taylor et al.) and social systems theory (N. Luhmann et al.). The empirical analysis shows that PowerPoint documents created for cross-project learning purposes contribute to an invisibilization rather than a visibilization of decision processes and their contingency. In the light of these results, existing efforts to promote knowledge management based on the learning-from-mistakes principle need to be reconsidered with respect to their realization in communicative practice.