Purpose-Entrepreneurial coaching appears to be a sufficiently customized way to help novice owner-managers develop their managerial skills. However, its usefulness remains to be verified. The purpose of this research is thus to examine the effectiveness of coaching as a support measure for young entrepreneurs and to identify the factors likely to have an impact on the success of coaching initiatives. Methodology/approach-Given the exploratory nature of the study, a flexible and open approach was chosen in order to explore the concept of coaching in some depth. The strategy retained was the case study method, with inter-site comparisons of six (6) coaching initiatives. Findings-The findings suggest that the success of a coaching relationship is explained by a set of factors or "winning conditions," some of which are more important than others. The most crucial one appears to be the entrepreneur's open attitude to change. Research limitations/implications-The main limitation of this study is the small number of cases observed. Practical implications-This research provides valuable information on coaching initiatives by means of real-life examples. It also highlights several factors likely to improve the delivery of coaching services to novice entrepreneurs. It will thus prove useful to those designing coaching programs for entrepreneurs. Originality/value of paper-Given the lack of documentation on the subject of entrepreneurial coaching, this paper has the merit of identifying some of the elements likely to contribute to the success of coaching initiatives. In addition, its findings will fuel thinking on how to enhance the benefits of coaching for novice entrepreneurs.