This is a great thread! From my perspective, if a job sucks, it's usually because the projects are managed poorly. Here are some things I ask to try and gauge how projects are run:
1. Do you subscribe to a particular development methodology?
This is basically a warm up question. 99% of the time the answer is agile. If it's a startup, they might say "we're moving towards agile." That's a good answer bc it means that you might have an opportunity to help them make agile not suck so much.
2. How long are your sprints
Two weeks is a good answer in my personal opinion.
3. What kinds of meetings do your dev teams have on a regular basis and how often do you have them?
The bare minimum for agile would be something like daily stand-ups (i.e. "scrum") and sprint planning once before each new sprint. Some shops do retrospectives, which are a complete waste of time in my opinion. There's also grooming, kickoffs, and all kinds of other crap.
4. How long are your stand-ups typically?
I'm looking for 15 minutes. If the answer is an hour they can go fuck themselves.
5. Do PMs write separate stories for front-end and back-end?
This is a biggie. Unless you're all full-stack devs, one story for front-end AND back-end is a pile of shit, especially for the front-end devs. You're going to waste so much time explaining the status of such and such story and who is blocked on what BC there is no way in Jira to say that the front-end part of story FUK-123 is blocked story is blocked by itself.by the back-end part of FUK-123.
6. DO YOU HAVE AN OFFSHORE DEV TEAM?
This is another biggie. I don't think I need to explain the pitfalls here, but if the answer is yes, you're going to want to ask a lot of follow up questions.