I've asked it so often and been in so many different teams I can more or less tell what the working environment and management will be like now.
Generally they aren't expecting this question so you catch them flat footed and get a clear unfiltered emotional response. The emotion on there faces betrays them. Every team has pain points, they have to answer the question with something negative, but its how they react with them that gives away a lot about the work place.
From a good teams you'll get a chuckle or story, which indicates to me a culture of understanding and dealing with things sensibly. Sometimes just a smile followed by a negative statement like "well releasing is problematic". But its that initial positive reaction.
From bad teams I've seen panicked looks between interviewers to make sure they don't divulge something, people turning white/clammy/sweaty, refusals to answer/insisting to move on/changing topics, silent stars at me LOL anything thats not openly a positive emotion.
Thanks for sharing. I'll use it from now on in job interviews.
I manage a small team and was wondering what I would say if asked this question--probably that our pain points are our server hardware/software, which are a bit, shall we say, "antique". Some of the other pain points fall out of that one.
And during the phone or in-person interview you can ask questions about team dynamics, like who you report to and are working with, how long the interviewer has been working there and how they like it, etc., to try to get a sense for how things work.
And I'd say ask as many questions as you can reasonably think of--it's more about how they answer questions than the answers themselves.
If they show resistance or evasiveness, then that may be a bad sign.
You can usually spot it in the job ads themselves (look for "fast-paced," frequent references to "deadlines," and similar language).