For senior positions especially, getting on to things that "went bad" right away in the beginning of the interview might be counter productive. It makes the per

For senior positions especially, getting on to things that "went bad" right away in the beginning of the interview might be counter productive. It makes the person uncomfortable. How about seeking his advice(genuinely) on a problem that you are facing. Or telling him about a situation where you personally fucked up and ask him how would he handle it. The purpose is to build trust and to do that it is extremely important to be genuine, not just sound genuine. The middle of the interview should be reserved for a bit of uncomfortable talk where you talk to him about something that went bad. Thrash some of his ideas, question a few approaches and let him react to it. I also try to make it point to make him work on a situation where he doesn't have control over a few variables(like the stack, or the timelines, or the people or the requirements). I keep the last few minutes for agreement, the conversation should leave a happy memory after all.