Yeah, I think you're "doing it wrong" as much as I hate to say that, sorry.

Search is keyword-based, like large-scale search is pretty much anywhere. Expecting "specifications" to match "spec" is expecting too much, same as expecting half your search to match a folder and the other half to match a file the folder is in.

The main thing to keep in mind is that search is content-based, not just filename. So instead, search for key terms you think are in the file, as opposed to focusing on folders/filenames. Start with one or two, then modify or add as necessary to narrow down.

True, although this is Google we're talking about and Google [web] search is smart enough to do a lot of statistically-driven NLU-type things on top of pure keywords...

(I currently work at Google, but not in Search or Drive / Docs...)

Google Photos search is magical.

So basically you have to search google docs like you used to search the web before google came along and revolutionized search?

> Expecting "specifications" to match "spec" is expecting too much

When I use Google to search the whole web, it DOES match. So how come it doesn't work when I search a small document?