It's clear that you're a very analytical person and I can very much appreciate your analysis of the situation, but I think you've missed a more fundamental thin

It's clear that you're a very analytical person and I can very much appreciate your analysis of the situation, but I think you've missed a more fundamental thing that went wrong with your interview. While it's absolutely true that answering questions at a different contextual level from what was expected will give a negative impression, it's also true that it's very difficult to discern what contextual level an interviewer is expecting from just the question alone and not all interviewers have the same expectations. But what I can assure you of it that at some point when you were veering off track from what your interviewer was looking for, your interviewer was sending you signals that you ignored. They're often very subtle and usually unconscious on the part of the interviewer, but if you can attune yourself to those subtle ways in which they're reacting to you, you can then vary what you're saying (and, just as importantly, how you're saying it) to meet the interviewer's expectations. There will be interviewers who want to hear abstract, high-level thinking like you exhibited in your interviewer. And there will be interviewers like the ones you met with that will want the opposite. There will even be interviewers like me that try to get you to do some of both and to be able to read my reactions to gauge which I'm expecting. Because for high-level engineering positions, this in itself is an invaluable skill. As a VP of Engineering, you'd need you to not only have technical chops, but also be able to read people. Whether it's a meeting with board members or knowing ahead of time that a key engineer intends to quit, reading people is an important part of the job. Tuning your game plan going into an interview is very important, and I think this experience has helped you do that. But if you're not able to be contextually fluent, you won't be able to make the on-the-spot adjustments necessary to really nail the interviews. Some great resources on this come from the world of poker, where reading people and concealing your own intentions is a large part of the skill involved. There's also good research from law enforcement on interrogating suspects. Both of these fields are too adversarial to be directly applicable in most situations, but they provide good examples of the kind of concrete things you look for to gauge someone's response.