The Aston Villa boss has been honest and open about both.
Indeed, Villa let the winger go and he is now hitting form with Leicester City, who face Sherwood's men this weekend.
And the coach admits the Villa Park outfit would have done things differently had they possessed the gift of hindsight.
Sherwood is quoted as telling reporters: "That can happen. If we had a crystal ball we would know differently but unfortunately for Villa it looks like it might not have been the correct decision. But we can't worry about that now, it has been made and you move on."
Meanwhile, the Aston Villa boss has also made the bold claim that he can't ever see Gabriel Agbonlahor leaving the Midlands outfit - presumably until he retires.
Sherwood is quoted as saying by the Royal Sutton Coldfield Observer: "He's got a massive part to play both on and off the pitch at this club.
"These next three games are what Gabby's all about. Gabby's an important part of this football club and to be honest I can't ever see him leaving."
But how will fans feel about the manager's quotes on Agbonlahor?
The Aston Villa forward's struggles have led to plenty of criticism so far this season and Sherwood standing by a loyal player makes sense. But standing by a struggling player unconditionally?
Sherwood has always been a man who has his favourites - like Emmanuel Adebayor, for instance - but he shouldn't be afraid to wield the axe as a Premier League manager. Might it end up costing him points if he doesn't?