In this chapter top-managers’ “tweeting” practice is investigated as a current challenge for organizational and management communication. The empirical analysis of selected tweets conducted by Siemens’ CEO Joe Kaeser shows the emergence of the role set of the “microblogging manager” within the triangle of a critical audience, the managers’ self-presentation and their occupational position as decision-makers in companies. Research conducted so far has mainly focused on the (organizational or personal) intentions or styles of Twittering, but has left out the constitutive role of the audience and its assessment of CEOs’ tweets. Future research will have to take the interactional aspect of Tweeting into account. The chapter starts with theoretical reflections on digital management communication from a combined sociological and pragma-linguistic perspective, elaborates the basic structure of Twitter, discusses current findings, presents results of the analysis of CEOs’ tweets and discusses their implications for further research activities.