Purpose: Through a survey of firm’s experiences with strategic alliances and a structural equation modeling approach, the aim of this study is to stimulate further interest in modeling and empirical research in the area of N-loop learning. Although the concepts of single-loop and double-loop learning, in particular, are well established in the literature, limited research has been directed toward their empirical validation and finer understanding. Design/methodology/approach: Based on a large sample of technology firms, a MIMIC model is proposed and tested with respect to the development of collaborative know-how via the adoption and conduct of different structural choices on how to deploy strategic alliances (single-loop vs double-loop approach). Results are cross-validated. Findings: Based on the results of two structural equation models, the findings support the fit of the proposed conceptual model and the notion that, overall, the greater the extent of double-loop over single-loop learning, the higher the level of collaborative know-how derived. Originality/value: The call for the empirical investigation of N-loop learning is met by providing an example of survey-based research. The possible benefits of “double-loop” over “single-loop” learning are modeled and tested empirically.