One of my questions was just closed with a somewhat questionable custom close reason:
I'm voting to close this question as off-topic because it sounds like you've spoken to him about it a few times already, at which point it's no longer a Interpersonal Skills issue (of how to discuss it with him), but rather a The Workplace and/or legal one (of what options or obligations you and he have).
It seems like this reason for closing is a little thin. Many of our questions on this site reach the site after the OP has tried to resolve the issue and failed, and I think we've established, with roughly 100 questions tagged work-environment, that questions stemming from workplace situations aren't inherently off-topic.
I think the question was largely judged the way it was because I also self-answered and that answer focused on explaining possible legal consequences. It's worth pointing out that answers don't make questions off-topic, questions and answers should be judged independently. Even if you feel that it being a self-answer changes how the question should be judged, explaining potential worst case scenarios could be a valuable last-resort interpersonal skill.
So, should this question be re-opened?