A disclosed method may include (1) providing a graphical drag-and-drop icon for visual presentation to a user within a user interface of a software application, (2) detecting a drag action performed by the user on the graphical drag-and-drop icon relative to the user interface, (3) detecting a drop action performed by the user on the graphical drag-and-drop icon relative to the user interface, (4) determining, based at least in part on a location of the drop action relative to the user interface, that the user dropped the graphical drag-and-drop icon on a specific feature of the user interface, and then in response to determining that the user dropped the graphical drag-and-drop icon on the specific feature of the user interface, (5) providing help documentation associated with the specific feature of the user interface for visual presentation to the user. Various other systems and methods are also disclosed.