You said you don't trust your new social group yet. You've been burned too many times. You asked:
How does the new person distinguish between googlable question and company specific
The answer to that is to try and Google it. If you get a result, it's probably Google-able and you can go further from that if you "don't trust the new social group yet". If you trust the group, ask them. You're the one that said they needed to be super cautious, so don't put that on me.
Do tell me, what stuff did I say one should ask about, that the team should explain in the first place? Why would these questions not be reasonable?
What I can tell you is that we have a `README.md` in every service. We have our onboarding docs directly in the source as well as markdown files. Every new developer's first PR is to improve the onboarding documentation. Regardless of that, most developers do find something to actually improve, even if it's just adding a cross-referencing link between docs or moving stuff around, so that it's documented in the right place in the onboarding flow. Of course, if your documentation is perfect for every situation and every type of person I commend you. In my experience, there's always one thing or another that someone doesn't understand or where a step is missing. Not because it's secret, but for example because everyone (so far) thought it was obvious. Take the example of a command you're supposed to run but replace one or more of the parameters with your own values.
So let's actually make an example of something where people should ask because it's not Googlable. Take an imaginary part of some setup documentation like for example
Replace the parameter with your own baseUrl you chose in step 1 and run `someScript.sh https://example.com/yourBaseUrl` to create the basic setup.
And they literally copy and paste this
without changing the parameter, even if the documentation tells them where to get this parameter from and to replace it before running. This is not "Google-able" if this is an internal script and while it's definitely on some level "not so smart", we've all misread something, skipped a sentence or overlooked a parameter that wasn't properly marked and I'd rather they just ask than take 3 hours doctoring around and not getting a single step further.
One improvement the next dev might make is to change it to
Replace the parameter with your own baseUrl you chose in step 1 and run `someScript.sh <yourBaseUrl>` to create the basic setup.
You know what's gonna happen? Someone
will come along and copy and paste this straight without thinking and take 3 hours to get anywhere.