Spurs sold Caulker in the summer to Cardiff.
Sherwood said: "Steven is a man. Even though he has been a kid, he has always been a man in stature.
"He knows what is right and wrong. He is willing to learn and he is willing to stand up for his beliefs. I like that.
"There are too many side-parting Smedley kids about. It is good to have a character, someone who might be harder to manage but is a good player. The club made the decision to let him go. It happens. You have to grant the wishes of the player. Steven wanted to go and play.
"He wanted game-time and more than the previous manager would guarantee him.
"The club decided they would let the player go and they think they had a good deal. It is up to Steven to build on that and prove the club were wrong to let him go."
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