Designing intelligent services for workplace learning presents a special challenge for researchers and developers of learning technology. One of the reasons is that considering learning as a situated and social practice is nowhere so important than in the case where learning is tightly integrated with workplace practices. The current paper analyses the experience of more than 10 years of research intending to offer intelligent services through capturing and leveraging knowledge structures in workplace learning. The reflection looks at results of several European research projects that have promoted this view. From this analysis, I arrive at a dichotomy of guidance versus emergence that describes how the technologies foregrounded one or the other, and what the effects of these design choices have been. I derive conclusions for dealing with this design trade-off in terms of conceptual, technological and empirical research.