I'm torn on this. It's possible he would be very receptive and appreciate the frank conversation. It's also possible he will wonder where I get the gall to suggest to him, in however a constructive or trying-to-help way, that maybe he doesn't actually want to be CTO anymore and should consider giving up his role. He's not the type to freak out on me or anything like that, but it could sour the good relationship we have.
