Hmm, I don't know of any that go beyond tiny examples like a simple image viewer or text indexer, except some old "game engine" books that walk you through building a Wolfenstein-type semi-3D engine. You might be better off coming up with your own project (Yet Another Media Player, My Happy Thumbnailer, etc.) and asking people for advice if you get stuck on the design. That's more realistic anyway -- manangment tells you to design a doc-to-database app, you're on your own on how to implement it.
But you might get better responses if you're a bit more specific about what you'll be doing: UI-oriented or web/batch oriented? How big of an app? High-level design or down to the code level?
If it's just high-level management you're trying to learn, a programming book is probably the wrong choice anyway -- books on UML and some of the MS Press books like "Code Complete" might suit you better.