It’s funny. Back when I was a senior in college, interviewing for what would be my first “real” job after graduation, I interviewed with every major defense contractor and computer company that came on campus. All the recruiters had only the best things to say about the company they were recruiting for. Not a single one of them contacted me for a second interview.

But during that same time, I also interviewed with a guy from the Defense Communications Agency. He told me that he knew I had interviewed with a lot of other companies, and that I could assume all the things those recruiters said were also true of working for the government. He then followed by saying he wanted to focus on the disadvantages of working for the government.

He really impresssed me with his honesty and forthrightness. When the call came for a second (phone) interview, I didn’t hesitate. When the tentative job offer came, I didn’t hesitate to take it. They took more than a year to complete the initial background investigation, so I also got a chance to squeeze in an internship that summer before starting to work there in August of 1989, while they continued to finish the investigation which would result in my TS/SCI clearance and the rocket-fueled start to my career.

I still remember Mr. Brewer’s name, and am grateful to him to this day, for helping me get my start in this business.

In my case the question has often unearthed things about the team culture that may work well for some and not so well for others. One example: a person I had an interview with told me that he wouldn't recommend a candidate to join the team if said candidate e.g. wouldn't get along with the typical "tech bros" team culture, which obviously wasn't something mentioned in the job description. For me that was clearly a no-go, for others this wouldn't be much a problem because the job in general was a very interesting one and very well compensated, too. OTOH, I've also heard non-trivial things in other interviews which were not mentioned in the job description but weren't a show stopper for me.

I also use the questions to learn more about the person and culture: if all people say "there is NOTHING I would change, this is a dream job" there is a very high likelihood that this is an environment where you don't speak openly about ways to improve and where individuals keep their criticism for themselves.

Success in what way?

This tends to take place at the very end of the process and discusses some of the flaws of the workplace and/or goals of the candidate ("you mentioned wanting to do compiler design, but as a webdev shop, it's unlikely we'll ever do that. Are you ok with that").

I think it establishes a tone of trust ("hey, we aren't perfect, but we think this is a good fit anyway").