Obviously, Matins (first light) and Prime (sunrise) are easy if it's not overcast, and a sundial would cover the rest. But if the weather was being a bit too British, that wouldn't work. And Compline occured after sunset in any case. Most mechanical systems hadn't been invented, and would have to be re-calibrated often, since the length of the hours varied with the season.
It doesn't totally answer your question, specifically, but I asked something similar recently and /u/imaginarystudy was kind enough to give me an answer.
https://www.reddit.com/r/AskHistorians/comments/5iwhae/how_did_medieval_monks_keep_time/