One of the best media presentations for insight into how clueless the Obama White House was is the documentary "The Final Year."There’s a difference between personal incompetence and organizational incompetence. One of the common trends you hear about from anyone who has worked with the system whether in it (like soldiers), or as outside consultants (Contractors I’ve met and people like Armstrong), or disgruntled upper levels of it, is that these organizations are generally not operating in reality because any bad news tends to get filtered out by middle managers who don’t want to look bad long before it reaches any actual decision makers.
Generally SOMEONE inside the organization does understand what’s going on and what to do, but the people making decisions do not.
Look at the military and compare how competent your typical veteran who got out as a mid grade sergeant or junior grade officer is vs. the raging stupidity of the generals.

The Final Year (2017) - IMDb
The Final Year: Directed by Greg Barker. With Ben Rhodes, Samantha Power, John Kerry, Susan Rice. A chronicle of the Barack Obama administration's foreign policy team and the events of Obama's final year in office.

The film was supposed to be a hagiographic salute to Obama, but instead it unintentionally highlights what a bunch of morons they all were. It shows that they did nothing but watch MSNBC all day while working at their desks in the White House and that when it came to understanding what the American people wanted or needed, they were completely in the dark. Trump made the same mistake when he put a bunch of Republican loyalist stooges on his staff. Those kinds of people are often completely incompetent when they're put into positions in the government in which they actually have to deliver effective programs and decisions. They live too much in an ideological bubble.