I compared it to interrogation because it's about steering the conversation. The only reason you're talking to middle management is because their work is getting outsourced to SaaS.

If you waste too much time on irrelevant topics, you lose. If you don't collect enough information, you lose. If the middle manager feels threatened, you lose. If you don't have a good production release, you lose. If there are any high severity bugs, you lose. If there are too many bugs, you lose.

The only way to win is to carve an exact path through the mess from the beginning, and that needs human experience.