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On Friday, August 13, 2010, the Silicon Flatirons Center convened leaders from the legal, academic, and software-related fields to discuss recent and future developments in transactional law due to changes in technology (the “Roundtable”). The Roundtable analyzed how accelerating adoption of technological “enablers” is qualitatively affecting business models for the provision of transactional legal services. Participants saw some novel business model innovations as “disruptive,” and others as “sustaining,” but in the aggregate the Roundtable participants agreed that the practice of transactional law is undergoing notable, significant and irreversible change. Participants agreed that the core value of legal services is in the exercise of sound judgment and in the relationship between lawyer and client. No participant felt that the importance of judgment would be diminished by adoption of digital technology. The group observed, however, that technology is altering how legal judgment is acquired and, moreover, is altering relationships between attorneys and clients. Participants expect these changes to accelerate as legal models increasingly leverage technological enablers. The Roundtable discussion revealed how new practices pose destabilizing challenges for valued elements of transactional lawyering. In particular, participants wondered whether increased automation, geographically distributed nature of work, and fragmentation of legal services would erode the ability to develop the “judgment” which forms the foundation for the attorney’s role as a client’s “trusted business advisor.” Participants expressed particular concern for the development of young attorneys. Namely, as the work done by first-year associates becomes routinized and fewer entry-level positions exist, how will a new attorney develop the pattern recognition and familiarity with granular aspects of documents sufficient to inform good judgment? More broadly, even for more experienced practitioners, as legal work is increasingly compartmentalized and decentralized, these trends present unique challenges for attorneys to gain a “big picture” understanding of a client’s business sufficient to provide advice well tailored to a client’s needs.