The game of American football requires football coaches to be able to develop crucial in-game decision-making skills within their players. It is particularly challenging for coaches because the many different positions played on the field demand training for different types of decisions. This chapter first explains some of the unique features of the chess-like game that coaches engage in to position players for success. Next, we share different models for understanding how coaches might think about the decision-making process and the development of decision-makers based on work with tactical (military) decision-makers. Then we present a way of thinking about tactical understanding that comes from rugby coaching. Finally, the authors consider some methods that could help coaches enhance the development of players’ decision-making capabilities.