Several ways to look at this IMO....

the dialogue could be going in multiple ways....him staying on, him staying within the organization higher up as his grandfather, him leaving all together.....The discussion could also be about how he feels about the team as they stand and what needs to be done moving forward....Step back, take some time, think about upgrades, where, who etc.......Whatever it is, the draft will swoop in quickly and the minds need to be solely on that IMO......