Sherwood has moved upstairs at Swindon and now fulfils many of the responsibilities Levy bears at Spurs as the Robins' director of football.
“You have to identify a player's progress very early," Sherwood told Squawka. “If he starts to improve you have to nail him down and make sure you get him on that long contract.
“Daniel Levy is a master at this, he's a great operator. Gareth Bale, for instance, possibly had seven contracts when he was at Tottenham. In the end the lure of Real Madrid was too great for him to stay and the money was too great for him to turn down.
“But Daniel is a good operator and a very good example of nailing players down very soon. If you wait until they're superstars and you've only got 18 months left of their contract then you find yourself in a sticky situation, other teams show interest.
“Once they show interest if that club is on a par or bigger than your club you've got a problem to retain that player."