An intelligent digital coaching playbook and related methods and systems are provided that automatically convey a freehand drawing to a structured, relational, and classified database to improve related coaching processes, make plays searchable, and enable analytics. A method for receiving input into a technology driven athletic intelligence system includes receiving, at a computing device, user drawn input describing a player assignment, while receiving the user drawn input, monitoring using the computing device, slope changes of the user drawn input and time interval changes of the user drawn input, using the slope changes of the user drawn input and the time interval changes of the user drawn input by the computing device to identify a pivot point associated with the player assignment, and re-drawing using the computing device, the user drawn input using the pivot point, slopes of the user drawn input and distances associated with the user drawn input.