Leadership 2.0 is a set of alternative management values and practices driven by a set of coherent assumptions about the nature of human communication. In this paper, the authors argue that Leadership 2.0 is critical to make Web2.0 work. This paper is informed by Dervin’s Sense-Making Methodology (SMM) as an approach to design knowledge sharing platform incorporating Web2.0 features which allow user-generated content and have a stronger emphasis on collaboration and interaction amongst users. SMM is a philosophically derived approach which allows knowledge management (KM) researchers and practitioners to more fully understand and listen to user’s needs so as to inform the design of dialogic KM practices and systems to promote knowledge sharing. This paper presents a “Safety Moment” project to illustrate how SMM has been applied to inform the design of a Web2.0 enabled ‘knowledging’ application in Environmental Resources Management (ERM), the world’s largest all-environmental consulting firm. The project discussed has been implemented since January 2008 as part of ERM’s commitment to improve Health & Safety Performance to ensure all ERM employees, contractors and clients are safe at work. The use of SMM informed Web2.0 application has correlated with increased staff satisfaction, increased company reputation and reduced risks.