Abstract: A guided outlining system to assist the user in developing strategy-specific outlines for business communications. The user is prompted to enter the target audience, purpose and specific content entries for the business communication. One strategy choice from a predefined list of strategy options is also selected by the user. Strategy guidelines are displayed for the user to assist in the organization of the content entries based on the selected strategy. The user is then prompted to assign type attributes and ordering criteria to each content entry. The content entries are then sorted and displayed to the user.