I've always been a very free player, way before i started seriously playing jazz. Improvisation has always been deeply set into my bones, sometimes to my detriment. I have a good friend who is a piano player but coming from jazz on the opposite spectrum. He has fantastic technique on the instrument and can play very technical material, note for note. The problem is he can't seem to get comfortable improvising and playing in a more free manner. He relies heavily on transcription, and actually performs those transcriptions. He texted me this morning about a great idea he had. He wants to transcribe a set of Oscar Peterson tunes and perform them with me as a duo, he would play note for note transcriptions of Oscar Peterson. I thought this was a horrible idea, for so many reasons. One being i respect Oscar and his band members so much that i would never dare doing a half assed tribute to him. Two being i have no interest in playing transcribed material, or even alongside someone playing transcribed material for a whole gig. I think i kind of hurt his feelings when i essentially trashed the idea and said i would prefer we just play using our own voice within our own arrangements of tunes we like. He confessed his own voice is weak and that playing these transcriptions will help him develop it. While partially true, he has been saying this for years at this point and has transcribed quite a bit of material. How do folks teach others to become a more free player and embrace improvisation in a group setting? I want to find ways to coach him if at all possible. He's a great player but needs to find his own voice in jazz.