That reminds me of when my friend Emma was trying to find a new job. It was a huge struggle for her and she never ended up finding a permanent position before she had to leave the country. She would get so upset and wonder what it was about her information that wasn't even getting her follow-ups or interviews, let alone a job offer.
Well, I actually don't know exactly, because I don't know what kind of information she was asked for or what kinds of things companies can find out about applicants otherwise. But, she was really ill-suited to the whole process. Despite getting extensive help from a number of different people, including professionals, she managed to send out a bunch of resumes with major mistakes. And she always had a lot of trouble reading and following directions--as for the various job application websites--so it wouldn't surprise me if she was filling out things incorrectly or inadvisably. Plus there was the whole thing about when her visa would be up, so a company would have to go to more trouble to hire and keep her. And there were weird things about her career history as shown on the resume, like most people do XYZ and she did ZAY, which could have been for a bad reason (and it was, in part).
How do you say that to someone, though? "Well, I think your problem is, you took twice as long to get your degree as you should have, which makes it look like you don't know what you're doing. And most people take this path, but you took this one, which suggests you might not be really committed to this industry. So, if you go back in time eight years and redo everything the normal way, that should clear it up."
I mean, there's no point in saying that. Or, "Well, having known you for five years, I'd say you're probably massively screwing up the application process each time." The only thing she could really easily fix were the typos on her resume. I know some people can turn weird circumstances into a great cover letter, but she wasn't that kind of person, and trying to explain how would have been like talking to a brick wall.
Even if a person wants to be a friend and answer honestly, sometimes the problem is so huge that there's almost no way to fix it, at least not without years of therapy or something. I don't like to leave people with no hope. If I can find something small and fixable, like typos, I might go for that.