Would be nice to see how and what makes him jump to the next step.
I know that for me one thing that helped me a lot was jamming over drum loops. I use them a lot and take the more complicated ones and try to follow them rhythmically. This I find is the best way to, like plantronic says, "switch between your 'metronomic' self and your 'phrasing' self". It forces you to adapt to the drum thus breaking away from the constant 8th and 16th :)