The nature of work continues to evolvefrom predictable, deterministic patterns toforms that are more contingent and idiosyncratic. The evolution of work and of the expertise needed to perform it have not been accompanied by innovations in the models used by workplace educators to develop this expertise. For some technical work roles, present models are inadequate for developing the skilled performance the roles require. Using in-depth accounts of actual work activity, this article examines changes in how work is accomplished. Emergent themes from selected work settings are analyzed against present models of employee development. Using the theories of situated learning and distributed cognition, a reconception of the role of learning intewentions is proposed that more fully integrates learning with working.Some contemporary work roles require a significant amount of work activity that is contingent and hard to predict (Darrah, 1994). Today's work environments are increasingly characterized by change arising from multiple factors, increasing the likelihood that workers will face novel and ambiguous problems (Howard, 1995;Weick, 1990). This places demands on workers that are difficult to specify and prepare for in advance (Barley and Orr, 1997; Mirvis and Hall, 1996). In addition, the expertise for work is increasingly distributed across members of work groups (Hutchins, 1991;Katzenbach and Smith, 1993). Even the environments for work are becoming fluid, as communication technology enables productive work from almost anywhere (Apgar, 1998) and organizations evolve into new, boundaryless forms (Handy, 1989).Developing the expertise needed for skilled performance in this environment has become a seamless and ongoing process. To ensure an adequate stock of work skills, workers are continuously adding, replacing, enhancing, and retro-fitting their expertise, as changes in the marketplace, technology, and work processes gradually eliminate the need for old skills and necessitate the development of new ones (Adler, 1992; Carnevale, Gainer, and Shultz, 1990).