I don't think you really can. In my experience, it's in the employer's best interest to hire good people, and it's not in their best interest to be candid with

I don't think you really can. In my experience, it's in the employer's best interest to hire good people, and it's not in their best interest to be candid with you. Furthermore, even if I as an interviewer worked for a shitty company, it's still in my best interest to hire good people so that the company becomes less shitty over time. Therefore, there are very few questions you can ask that will give you a good insight as to whether a position is a dead-end job (whatever that means to you) or not. I'm not going to lie to you, but I'm also going to spin it in the most positive light I can to entice you to join my team. At my last interview, I had a lot of success pretending that I was the one interviewing 5 people rather than being interviewed by those people. I asked a lot of questions, tried to get a sense of their day to day. It turned the interview into a bit more of a dialogue and less of an interrogation, and I think I got to see a bit more about how those people worked and what they thought during their time with me. I asked them a lot of the same questions I ask candidates when I'm interviewing them. It worked pretty well. Got an offer. Wound up declining, because I sensed it wasn't a role I wanted, but I don't think any particular question gave me that impression. Anyway, I don't think you can really find out in an interview. I think you'd have more luck talking to people outside of the interview or reading Glassdoor reviews, and so on.