Just my twopennyworth - I think that trying to teach someone the ability to improvise, is very difficult. It's a 'feeling' - almost something which you are born with - a bit like having a natural' sense of rhythm' or a natural 'sense of harmony' - some have it : some don't have it
By the way Chuck, the pianist on Diana Krall's recodings is none other than Diana Krall
She is the greatest!!