Yes, but not the example you used
We should only be addressing situations that arise in a workplace, not questions specific to a workplace on how to achieve a goal (like the example, which should go into the work se). If he wanted to know about how to talk to his boss outside of work, or how to behave in a general chat with him inside work, that would be okay.
We shouldn't be giving advice on how people should behave in the workplace in terms of their jobs or how to deal with their bosses problems with them, but we should deal with personal issues they're having when interacting with a set person/people.
We don't want to take any more than the bare minimum of questions from another site.
Essentially the questions should be about a situation that you would normally face (such as a party or talking to someone) the only difference is that the environment is work. You should be able to take the question out of that environment and have it as a general question which is not obviously work-based.