What are your biggest regrets?
I had a conversation with my co-worker a couple of weeks ago about "fireside" chats that tech companies like to put on, and she share how annoyed she always felt when moderators would ask their interviewee "what was your biggest regret?" The issue wasn't really with the question itself, but more with the answer that it always got. The answer would always be "I don't have any regrets--it all worked out!" Or something along those lines. She proceeded to explain that, well, of course you don't have regrets right now--it's easy to say that when they're in the position they're in (read: successful and enough so to be interviewed at this "fireside chat"), and everything has worked out in your favor. In other words, it's privileged to be able to say that you don't have any regrets. It's easy to look back and remember how you had regrets, but taken in the context of how it "all worked out", they wer...