During the Industrial Revolution, the structure and methods of Western legal systems facilitated commercial expansion and technological innovation. But as the Information Age gradually re-shapes pre-conditions for successful innovation, legal systems generally—and contracting in particular—may be obstructing rather than enabling continuing growth. To re-align commercial and technical needs with legal methods, traditional legal systems must themselves innovate. This Chapter highlights three perspectives for imagining legal innovation: first, alternative structures for contracting, like relational/collaborative and outcome/performance-based contracts; second, information design tools like simplification and visualization, and computer coding tools; and finally, systemic measures designed to resolve the kinds of problems that have increasingly challenged traditional legal methods. Throughout, the Chapter adopts the attitudes and methods of Proactive/Preventive Law to untangle the difficult relationship between law and innovation: stronger innovation requires the law to offer diverse methods, flexibly applied, to meet varied contextual needs; and yet any new legal reform must be efficient and feasible as well as effective and just.