Imagine you start a job painting houses. You would not paint them the same way on your first day as you would after a year of experience or 5 years of experience. What have you learned? How do you work smarter/better now than in the past.

What experiences triggered that learning process, or did you just take orders from someone else with a more problem-solving oriented worldview.

The same applies to technical work. We're not perfect robots, we are given the freedom to figure things out, so the goal is a refinement of the "program" in our minds. The more effective/sophisticated that program is, the more rational we are.

Why don't you just ask for their self-performance reviews / retrospectives for the last n years of their current/previous job after you've filtered by resume? I suspect that unless they were expecting it (which isn't unreasonable since a lot of interviewers have variants) "remarkably unsentimental" people like John Carmack would blow this part of the interview. Why do you care about the step-by-step process of my programming journey, which is irrelevant to whether the current me can help you out right now? If you're trying to test for passion ("why'd you start house painting anyway and what drove you to keep doing it for so many years?") or self-awareness there's probably a better way.

I would consider asking for that too invasive. I think the important thing to get a sense of is how they look at problem solving as a function of expertise.

In other words, it's possible to be smart but not act smart, and it's possible to act smart while not being exceptionally intelligent.

I'm basically looking for self-awareness of one's own cognitive limits and evidence of a meta-process that seems likely to result in better decision making than whatever the raw intellect would offer.

I don't get how that relates to the question asked to me? I mean, it was a time I had a problem / failed that impacted production environment. That was the only one I had in mind, the guy looks like he was expecting a time I've put the servers on fire. It simply didn't happen.

Another thing is that my current environment IS very CTO pushy taking order and doing his view. Why stating this counts against me? It's not like everyone can take leadership in the tech stack / implementation.

I am a 100% sure that I would get into his (big) company and just follow orders as well. Of course having my implementation and my personal touch every now and then but still I wouldn't get to make architectural decisions or choose the tech stack.

Unless you're working in a 100% microservice architecture with hundreds of small people team deploying separated stuff I don't see how that can happen.