This study examines the signaling of anticipated organizational futures in shareholder annual reports of large scale technology organizations is the signaling of anticipated organizational futures. In revealing policy and technology change, these reports are predicting likely outcomes in their own corporate trajectory. With influential and large technology firms those predictions also impact the movement of industry change. This study subjects twenty years of the IBM Corporation’s annual reports, specifically the Letter to the stockholders from the CEO, to an intensive content analysis. We identify trends in these data and posit causal relationships between actual events and the foretelling of these events in the letter from the CEO.