Information discovery is a very diﬃcult and frustrating aspect of software development. Novice developers are often assigned a mentor who preemptively provides answers and advice without requiring the novice to explicitly ask for help. A similar situation occurs among expert developers in radically collocated settings. The close proximity enhances communication between all members of a group, providing needed information, often preemptively due to ambient awareness of other developers. In this paper, we propose a mechanism to extend this desirable property of preemptive mentoring to developers in more traditional software engineering environments. The proposed system will infer when and how a developer becomes blocked looking for information, and notify an appropriate expert to come to his aid. We believe that this preemptive help will lower developer frustration and enhance diﬀusion of expert knowledge throughout an organization.