The key to solving hard problems is to ask the right questions about them. In Sarah's example dialog with Sounding Board, she comes away with ideas for what research she needs to do before making contact with the client, who within the company she should contact, what points she should try to make, and what stories she might tell. The reason why this "structured brainstorming" session is so productive is that Sounding Board is able to pose fruitful questions for Sarah to pursue.
The program actually knows next to nothing about Sarah's particular problem. All it knows about are what types of questions are useful to ask when facing various types of challenges and how to present those questions in a sensible order. In some sense, Sarah does all the hard work in her session with Sounding Board. The program merely serves to shine a light on areas that are valuable for Sarah to mine for ideas.
Questions in Sounding Board
Where am I in the content of the book?