The guy had zero management experience, let alone for a large enterprise, etc.
Yet...he got far more of his reckless policies started/completed.
Why?
Not because of his vast government experience or his superior management skills.
He got more done because those around him thought like him, wanted to get what he was pushing done. He gave the "orders"...and they complied, with earnest.
And perhaps most importantly, the fed gov / media didn't have an ongoing coup against him.
Actually, Obama had quite a bit of government experience. Really, he only had government experience. His entire adult life was working as an ‘activist.’ What do activists do? They game the system - the system run by the government - to change their world. He saw first hand how government worked at the local level (as a ‘community organizer), the state level and then as a Senator.
He understood how deals get done in politics and how to make incremental but lasting change. This is an invaluable skillset to have when governing.
Trump entire life was the Art of THE Deal; he was a big deal kind of guy. Big Deals, however, don’t get done in DC. Instead, it’s a patchwork of tiny, little deals that moves the ball, incrementally. I’ll do you this little favor today, and you do me that little favor tomorrow. That’s how the sausage is made.
And while Obama didn’t have the personal management skills to make sure his policies were big implemented, he had worked in and around government long enough to populate his inner and outer circles with true-believers as you smartly mention. Trump came to DC with Jared & Ivanka both of whom were - wait for it - DEMOCRATS. Other than Larry Kudlow and Stephen Miller, that’s it more or less. He went through three or four Chiefs of Staff in four years and never had the kind of bruising consigliere that Obama had in Valerie Jarrett (and a couple others) who could make things happen.
For all these reasons, Obama was a surprisingly effective president, which is to say he was able to implement lasting change where Trump really wasn’t.