In this study we present online software to rapidly assess the impact of mentoring techniques on a novice entrepreneur. We have built a prototype that collects data from team members in less than five minutes and that automatically returns a diagnostic analysis to the mentor. Between 2012 and 2015 we have tested three versions of our prototype with longitudinal analyses of teams attending start up weekend competitions, to confirm that our prototype supports mentors with few and yet relevant information. The results of our studies open several avenues of research regarding rapid diagnostic of project teams, whereas, from a practical point of view, our prototype entirely done with Google Docs can be easily used by anyone interested in entrepreneurship education.