I mean yeah, he's asking stupid questions to the internet.
He doesn't ask his engineers, who've got better things to do than to answer his questions.
He likely thought "Oh, that route planning looks odd. Since I'm sure the engineers know what they're doing, this must be the ideal path, but I certainly am curious as to why that is. Hey X, why don't the planes fly in straight lines?"
It's a perfectly legitimate question to ask for someone who's job isn't engineering, but hiring people who hire people who's job is engineering.
He understands the business.
He doesn't understand technical details, which is something very different.
He tells people "go find the ideal route". He doesn't find the ideal route himself.
If a CEO of a large company attempted to learn all skills of every single one of his employees, he would spend a couple centuries learning, instead of doing his job.
His job being: Telling the right people to find the ideal route.
And he himself clearly isn't one of these people. And he doesn't need to be.
(You wouldn't expect Tim Cook to know every legal detail of all the countries he trades to either. Because that's not his job. His job is to hire lawyers who know every legal detail of all the countries he trades to.)