It didn't look like it at first, but Brooks's The Mythical Man Month often does outline, actually, though usually after an engaging few introductory paragraphs.
Imhof's Cartographic Relief Presentation does dedicate a few sentences towards the beginning of each chapter to the roadmap.
Anderson, et al.'s CouchDB: The Definitive Guide starts each with a brief outline-ish paragraph (nicely cordoned off above the first subhead) then proceeds wholeheartedly with the rest of the chapter.