Calderwood and his assistant Jimmy Nicholl are out of contract at the end of the season but he insists personal reward is not at the top of the agenda when these talks take place with football director Willie Miller.
Instead Aberdeen's most successful manager in a decade is looking for a clear indication that the Pittodrie club's board of directors will match his ambitions by providing more money to strengthen the side, says The Scotsman.
Calderwood said: "I will have a meeting with Willie on Thursday to discuss the way ahead but no-one knows what's going to happen in the future.
"If they say 'we agree with your ambitions but it's not going to be possible to fund them' then it's up to me to decide what I am going to do.
"If everything is alright then you stay but I need to know where they want to take things to and can they fulfil our ambitions to take Aberdeen higher.
"I think we have the same ideas but it's getting there as finances dictate a lot when it comes to that and I don't mean trying to buy players for a lot of money.
"The current team is doing well but we have done a lot of scouting at younger age levels and these players might still cost money to bring in to the club. You don't pick up gems for nothing in this day and age.