Leaders must have good planning skills in order to be successful. In this paper, we administer training of planning skills that addresses two major considerations. First, what are the key processes involved in planning. Second, what content do these processes work best in. This paper examines two key processes of planning: forecasting and identifying key causes. Second, this article examines two major forms of content including case-based reasoning and principle-based reasoning. It is concluded that the best process and content depend on the type of outcome desired and the type of individual being trained.