My Dh has been job hunting for about 2.5 years now. He's currently employed at a small company he's been with for about 20 years. Over the years his responsibilities have changed considerably as well as going from seasonal to year round. While it was a seasonal job he was also a tenured faculty member at a state university (served as chair his last year there). He's been interviewing at both private companies as well as universities and he is perpetually the second choice. He get's through the phone interviews is one of the two or three people brought in for in-person interviews and so far just one offer for a university position that was not a good fit.
My guess is the fact that he's been with this small company with no title change for so long he's not doing a good job of really describing his current job level of responsibility and management. He's in a niche market (non-profit entertainment) and it's really starting to get to him. How can he do some investigative work on why he's not getting offers? He's interviewed with companies that employ his former students/staff that have worked under him and still nothing. How can he do some recon to up his desireability to future companies?
Re: DH is always the second choice
I'm not really sure how to answer but as far as investigative and short of breaking in and looking at notes from the interview if there are any, he could try and contact one of his former students/coworkers and ask for input. I don't know if they would know anything but that is really all I got.
^^ I think doing that might really be ok. I think the way you put it above sounds really professional. He could do it in an email to keep himself from sounding weird or desperate (which would be my personal concern) or if he has strong and professional way of presenting himself he could do it in a quick call. Just let them know that he still has to look elsewhere, even though he wasn't the right fit for them, and he would really appreciate some constructive criticism.
If he doesn't want to do that, perhaps he could get with a head hunter firm and ask them to profile him and let him know how he can improve his presentation of himself.
ETA: I'm sorry you're having to go through this. I am actually pretty horrible at interviewing and "selling" myself, which I really have no excuse for considering my profession (corporate/legal).