Chris Poole's LinkedIn says he's a PM in Google Maps: https://www.linkedin.com/in/christopher-poole/
I've read on /g/ that he's been working on Google Plus. In the thread I read that, people were joking that he is going to get fired now that the project is sun-setting, but there was no real evidence to back that up.
Whatever he worked on while there is anyone's guess, could have been a dozen things, but mostly I'd guess he was probably working on getting the general program off the ground and self sufficient.
Then he worked on Hangouts Chat (replacement for Hangouts) for a REALLY short time (7mo it says) before moving to Geo. I wouldn't read too much into the brevity of his time in chat because the move to the Maps team also moved him to Tokyo. If you really want to live somewhere in particular it's not uncommon to decide what office you want to work in and find a team there to move to. My understanding is is that Poole really likes Japan, so this doesn't seem crazy.
Altogether his career progress looks... normal. Perhaps a bit of trouble finding a niche, but that happens. Just another guy trying to figure out where he fits in, what he wants to do. So, no real story here; nothing of particular note.
I think that is true. I heard he started some kind of message board like a decade and a half ago. Some kind of place for people interested in anime to talk with one another. :^)
I just assume every keystroke I make and everything I do is being logged and reviewed by someone while at work. I don't even log into any of my accounts at work because I don't want my employer stealing my passwords and covertly monitoring my email and social media communication. To say nothing of actual camera surveillance.
It's similar to how every employee understands that their manager has the capability of getting their corporate chat logs. It's one thing to have the capability and another to act on it. If a manager acts on it, it will almost always destroy any trust between the manager and his/her team. Within the organization, they will almost certainly be branded "that psychopath manager that reads chat logs" unless there was an exceptionally good reason to justify it (e.g. a legal reason).