> at some point why doesn’t the CTO / CEO / etc. say “I’m going to go have conversations with the workers to get their perspective?”

Why would you when all of the reports you're getting from your managers are 5/5 stars and "everything's great". Once an organization gets large enough, the information that reaches C-suite has been filtered through so many layers that it barely resembles reality anymore, even when you remove malice from the equation.