This paper deals with jet airliner pilots' "Flight Management Skill" according to their experiences. "Flight Management Skill" is "an experience-based skill which airline pilots should manage for flight safety, for economic fuel saving expenditure, for punctual flight operation and for passenger comfort." In airline companies, they stress more importance on training younger pilots with this skill, because the number of pilots with a variety of experiences is decreasing. In order to evaluate the relationship between pilots' experience and their level of "Flight Management Skill", the authors carried out flight simulation tests co-operated by airline pilots with various experiences. In this paper, the authors show the results of the simulation experiments by setting a scenario in which a wind shear arises just before landing. This scenario asks examinees to make important decisions based on the information and knowledge they have. Eight pilots with various careers participated in the experiment as examinees (four experienced captains and four co-pilots). To examine the outcomes of the experimentation, the authors recorded the examinees' utterances, flight paths, the amount of remaining fuel, and the interview after each experiment. These data were arranged into "timelines" and "decision trees" etc. and were analyzed to compare the difference of examinees' "Flight Management Skill". Some suppositions about experienced pilots' decisions were concluded as follows: Their decisions are made 1)flexibly according to the situation, 2)after considering the risks, and 3) relatively independent of external sources of information.