The purpose of this paper reflects in a study of an optimal development path in the ELECTRE-based stepwise benchmarking context. In the paper, multi-criteria decision-making is first described as a tool for stepwise benchmarking, where the ELECTRE MLO ranking method is used. In order to make the problem of finding the optimal path easier and significantly reduce the number of the paths that have to be considered, we are proving the theorem showing that it is better to make gradual progress than “skip steps”. As an illustration of these considerations, the ELECTRE MLO method is applied to the benchmark teaching assistants of one faculty of Belgrade University, according to the marks given by their students. We are looking for an optimal development path by using our theorem that substantially reduces the number of cases. We are also checking that the paths with no steps skipped are superior to the paths in which steps are skipped, in accordance with the theoretical result we have obtained. Thus, we are demonstrating that one should first look up to the colleague who is a little better than him/her, and then gradually improve until he/she has reached the level of the individual given the best mark.