A method of managing a drilling anomaly includes providing a computing device comprising a graphical user interface (“GUI”) that is configured to display a plurality of screens in response to detection of the drilling anomaly; displaying a first screen that includes a menu listing proposed actions to address the detected drilling anomaly and an estimated success rate associated with each of the proposed actions; wherein each of the proposed actions is selectable by a user via the GUI; receiving, by the computing device and via the GUI, a first selection command associated with a first proposed action from the menu; displaying a second screen that includes a first illustration depicting execution of the first proposed action that was selected by the user via the first selection command; and receiving, by the computing device and via the GUI, a command to execute one of the proposed actions.