I hear your concerns - and you are correct that phrasing of such questions can set the tone of the conversation. But I don't want to work in an organization that cannot have hard conversations about how they got to their status quo. If probing into their history is painful enough to them that it turns me off as a candidate, I'm fine with that. The best teams I've worked with had zero problems answering "Why", no matter if the answers were great or, "Yeah, that choice didn't turn out so well, and we need to improve." The worst teams I've been on were ones with defensive leadership.
I do agree with you 100% that answers that don't match personal preferences aren't red flags - everyone can learn from each other and expand their perspectives by working on new things with new people.
Even so, a tech leader who freaks out over being questioned is a red flag.
I didn’t say asking a ‘why’ question will freak people out. I’m just saying it is a suboptimal way of getting the information you want because it will affect the person you ask in an emotional way.
I do agree with you 100% that answers that don't match personal preferences aren't red flags - everyone can learn from each other and expand their perspectives by working on new things with new people.
Even so, a tech leader who freaks out over being questioned is a red flag.