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Hi Elizabeth and welcome to our community
Hmmm, me being a simpleton at heart, why not the following?
Create a folder where you will store these pages. Then create a page inside the folder where you ask the question: What are you trying to do? Then list the possible answers. Each possible answer leads to a different page. Each of the different pages either asks further refining questions or displays a list of potential topics.
In our 2.5K-topic merged WebHelp project, we've implemented a series of navigation pages similar to what Rick suggests.
Whereas the TOC is categorized by major features, the opening page provides links to pages for User Roles, Functional Tasks, Major Components, Menu Help (split between Client and System Administration), and Reference. (I used a free tooltip utility from Walter Zorn to provide a hover "peek" before they click to jump to a link.)
Each category within these pages has a list of the most commonly used topics. Therefore an "Operations & Technology" user would be provided lists of topics dealing with his normal duties such as Batch Processing, Imports/Exports, XML Messaging, etc.
Another method might be working with the developers to tie in privileging to apply to the help as well as the application features. You could "map" topics by using folders and/or topic keys, such as leading "sa_" for system admin, "bp_" for batch processing, etc.