A method of providing automated help includes receiving, at a computer system including at least one processor and at least one computer readable medium storing machine-executable instructions, user inputs for utilizing a plurality of functions of a computer program, detecting, at the computer system, a plurality of user actions utilizing the plurality of functions, as a function of the user inputs, at the computer system, an action trigger indicating a user help condition, wherein detecting further comprises identifying, in a help trigger database associating a plurality of action triggers with user help conditions, an action trigger matching at least a user action of the plurality of user actions, by the computer system, a first area of expertise associated with the user help condition, based on the identified first area of expertise associated with the user help condition, identifying, by the computer system, expertise to provide assistance to the user.