yes - i generally give tom no guidance whatsoever hah, i think his music is great and trust his taste so whatever he comes up with i know i'll want to use somehow. occasionally i'll bring up a specific thing, like the idea of a dedicated pop music style track for the Weepster section, or something will come up in development, like he offered to do a hallmark-style track for Heart Of The Killer, but mostly it's left loose what goes where.
i try putting different tracks to the levels when i'm playing through, often what works best is not what i was expecting which hopefully keeps things feeling surprising. i try to keep the same song between enough scenes that you get to hear the whole thing and then changing it up is a really immediate way to indicate a change in tone. sometimes i cheat a bit and play with the pitch to elide the feeling of just parsing the track as the same cue if it's used a few different places.
i've worked with tom since the goblet grotto days so over a decade, he's a great musician with really eclectic tastes and range so my main advice on this issue would just be for people to work with him specifically!