Traditional instruction is adaptive-that is, instructor-driven, face-to-face and/or online training to teach skills and knowledge and convey information, policies, and procedures. In contrast, generative learning is learner-driven, collaborative, and problem-focused. Web 2.0 technologies can support both types of learning but are especially valuable for generative learning. This article reviews learning processes and Web 2.0 capabilities, describes two case examples, outlines ways to design Web 2.0 training applications, and discusses the changing role of learning professionals from delivering structured, one-way adaptive learning to designing and facilitating generative learning opportunities. The article concludes with ideas for corporate education and research on Web 2.0-based learning processes, including utilizing the technology to track and improve learning.