I'd ask him what objectives are set out for the Manager at the beginning of each season in terms of team performance & what is the bare minimum expected?

I'd also ask him what the estimated Clubs transfer budget is every season and if extending contracts/increasing wages of existing team members are included in the budget? Also when we sell players is the money made available to the transfer budget? If so...where has the money gone from previous windows? I would also ask if a certain player was approached and wanted to join, whether the transfer budget would be flexible enough if the said player cost outside of the budget allocated.

Finally, I would ask him if he believes our current model is sustainable in terms of bringing success to the team?