I notice that when a political issue comes up that people reject, all of a sudden they start talking about "Leadership." it has apparently become a fashionable buzz word, especially to those who don't like the leadership being displayed. It isn't leadership that's the problem, but anything but their own brand of leadership that they denigrate. Republicans, especially, seem to like "leadership" that will send the country over a cliff. Anything less is a failure in "leadership."
LL
IMO, he used the term "leadership" in context of being able to relate to and communicate with average (less educated) individuals.
I clearly remember two examples of such social disconnect by Ivy League scholars.
George W Bush's (Yale, Harvard) comment at a fundraising dinner; "some call you the rich, some call you the super rich, I call you my base".
and
Mitt Romney's (Harvard) comment at a fund raising dinner on the 47% of US citizens who don't count.
Both comments were not intended for publication, but luckily they were and gave insight into the prevailing elite viewpoint of inherent superiority. IMO, these are the very attitudes fostered by their elite educational environment which William Deresiewicz was addressing.