What term do you describe a question which is about the inadequacies of the asker

Oh, the term in common, ordinary parlance is a 'loaded question'. In the law, we would call that a 'leading question'. It seems it's also called a leading question in psychology.

Could also be passive-aggresive.
Back-handed compliment.
Masked insult.

Self deprecating - if i parsed the question correctly .

We use leading question over here. When I was a civil servant part of the training was not to ask leading questions. I think I had an afternoon on it.

That's not self deprecating, self deprecation is having a joke at your own expense. That isn't the situation the questioner is asking about,he's asking what do you call it when someone puts someone else down because of their own inadequacies.

I think you might be right about what the OP wanted to know, but a strict parsing of the question is something else. The 'asker' is the one asking the question. The question is about the inadequacies of himself, not the one being asked the question.

For example - Am I being a nit picker? How do you think I got so popular on A2K?

The difference is between joking about yourself and projecting your inadequacies on others.

And the question addresses the former.

You've clearly never attempted standup.

Projecting ?