Could be the case, but some has insist the player himself 'badly' want the move, and Conte might not have an opportunity to offer him anything to stay though, he just let him go. Also Matic is still around, his future is still unclear at that time and Bakayoko on the verge to join. At that moment, Chalobah behind 4 players and it is normal he will want to leave, and Conte might not have try to convince him at all.
Now, when we are rumoured to sign the likes of Drinkwater and Barkley for 40m, if only we could offer the exact same opportunity to Chalobah if he is still around with no transfer fee involved. In my opinion, if we capable to convince Drinkwater or Barkley to come here, we're more than capable to do the same thing to Chalobah. Whether Chalobah not confident in his ability to be able to compete and would still refused to stay, is another thing.