The context and frequency of these types of questions is crucial. As an engineer myself, I would love to see more of these conversations as long as they’re handled the right way.
The point of these questions should be to encourage really creative thinking to break out of "normal" operating modes (take on tech debt, etc) and if that's not well understood, or perceived to be an instruction to crunch, then you haven't set the context appropriately and will burn people out.