Unfortunately, we're rapidly moving to an AI dominated work landscape, in many arenas.
What this does, is move the needle towards, what I like to call, "bean counting" analytics, where feelings, emotions, personal traits, etc are not entirely dismissed but calculated with "assessments" and as you said, "silly riddles" So you end up answering dozens of questions, oftentimes repeated questions, to gauge a person's emotional/moral value.
I've long since abandoned the idea of moving above middle management as I'm personally very big on work/life balance and to me, lower to middle management, and in some cases, even the ground floor, is the sweet spot for earnings+stress+workload. I am not interested in job titles or making a certain dollar figure. Some are driven towards those ends but I desire peace of mind, especially as I've aged. When I leave work, I want to largely be done with it. If I can make enough to pay the bills, and have a bit left over to invest/save, I'm perfectly fine.