There are red flags to bad environments out in an interview, if the place is really horrible. But looking very hard for problems in an employer during an interv

There are red flags to bad environments out in an interview, if the place is really horrible. But looking very hard for problems in an employer during an interview is a bit like looking very hard for problems in a candidate during an interview: The more you have been around the block, the easier it is to let those signals that aren't necessarily very strong to just take over, and that leads to failure. The interviewer with the least red flags is probably the one that is best at lying to you, or to himself. So what I do, outside of tiny startups (where I'd not go regardless, as you are in for years, and chances are you'll just be underpaid for the duration) is to go look for former employees, and ask them why they left the place, what sucks, what doesn't, and how generalized the problems are. People that have left might overestimate how bad the place is, but better an overestimation that you can temper than talking to someone that is still in love with the place, right? This mechanism has been pretty good for me, and you can show you are a well prepared candidate by asking pointed questions about what the people that left considered the place's most glaring weaknesses. I have been fortunate enough to be able to do this a few times in my career: In some cases, talking to my would be predecessor. It's helped me dodge big bullets, either by avoiding employers altogether, or by letting me ask for a different department/team in advance, avoiding terrible managers.