This article examines a new training design for continuing professional development that aims to support the learning of the novel knowledge and skills needed in emerging professional fields by interconnecting academic and workplace settings. The training design is based on using two advisors, one from working life and the other from an academic context. The article examined whether participants' personal orientation to adaptive expertise predicts the success of a guidance process. The interconnection of workplace and academic contexts was expected to occur through guidance practices. In addition, the features underlying the most successful guidance relationships were analysed. Data were collected by conducting repeated semi-structured interviews with 18 course participants, eight academic advisors and eight workplace advisors in the context of a 1-year energy efficiency training programme. The results indicated that a trainee's personal orientation towards adaptive expertise is a significant component in successful guidance processes. An interconnection of workplace and academic knowledge and practices was hardly found in the guidance provided by each participant's academic and workplace advisors. The feature underlying the most successful guidance relationships are related at the personal, dyad and context levels. An excellent match between the expert profiles of the learner and the advisor appears to be especially critical for successful guidance and powerful knowledge exchange in emerging fields. However, finding matching advisors is often challenging. Many problems are presumably solved if these "right persons" can be found and if the trainees are themselves oriented to utilise the novel resources provided to them by the advisors.