where he works

[azz]

a. John knows where he works.

This might mean John knows the address of his workplace, but could it also mean that he knows the place where he works (ie. he knows the environment, the people etc..)?

Many thanks.

[Erik_Kowal]

It is unlikely to be understood in that way. For that interpretation, "John knows his workplace" would be far preferable.

[trolley]

When I read that statement, with no context, my first thought was "John knows where who works?... Mike?...Gary?" As Erik said, it's unlikely to be taken as in your second option and I eliminated your first because, really, doesn't everybody "know where they work"?