A method, system and computer program product for assisting the authoring of electronic messages are disclosed. Operations performed according to an example embodiment may include: accessing an electronic message stored in digital form in a computer memory; inspecting the electronic message to identify intended recipients of the electronic message; gathering and analyzing historical data stored in digital form in a computer memory relating to a conversation history that links an author of the electronic message to the intended recipients; performing semantic analysis on the electronic message to extract words and phrases representing recipient fitness information that is indicative of whether the electronic message is appropriate for the intended recipients; generating a fitness result for the electronic message by comparing the recipient fitness information to the historical data and identifying inconsistencies; and outputting the fitness result for viewing on an electronic display device associated with the author of the electronic message.