For example, hypothetically, if one has a weakness regarding chasing down money and one knows their career path is likely to involve raising money, then one could get a fairly rapid education in the subject for the price of a few cups of strategically ordered coffee. Don't know the character of a VC? Thirty seconds of Googleage should give you the names of five compulsively chatty people willing to give you their take.
I can sort of see why, if one were busy, one would quickly burn out on explaining How To Email People A Question to folks who did not immediately see that in the solution set when they had a plan of action which required a bit of discoverable organic knowledge.
And to add to that what one person is able to pull off given their skills is not always possible by another person even if they have been told what to do or how to do it.
Seat of the pants feel involves knowing how to react and adapt when the situation changes ever so slightly (a nuance). It's impossible to prepare someone for every possibility that might come up. That's something that comes, as you said, from "from previous successful experiences".
The best advice I can give is to learn concepts as opposed to a specifics and to understand exactly why something (say in a negotiation) should be handled a certain way. It's like the difference between learning what streets to turn on in NYC and learning the way the streets and avenues run so you can arrive at your destination even if you miss a turn.
Think of yourself as an actor playing a role.