De Zerbi is in advanced talks to take the job after performing a U-turn on plans not to consider any offers until the summer after his dismissal by Olympique Marseille last month.
"For anyone going in now, you have to put a question mark on it because you've only got seven games left," Sherwood said on Sky Sports. "I like him, I really do. I like his personality. I said many months ago that he would be the man to come into Tottenham.
"I would've picked him over Mauricio Pochettino for the long-term because he plays that style that Tottenham fans want to play. He opens up the pitch - but not now. That style is not needed now, what they need now is a safe pair of hands. This is far from a safe pair of hands.
"I still like him. I love his personality and the way his teams play. But they can be open and can get hammered in some games - you can't get hammered between now and the end of the season."
Another former Spurs midfielder, Jamie O'Hara, is right behind the hiring.
"I am a bit annoyed and upset at Spurs fans who don't want him," O'Hara said on talkSPORT. "What planet are we living on? He is a top Premier League manager. He plays fantastic football.
"He is in the game, he knows the Premier League, he is fresh... we aren't talking about a Harry Redknapp. I don't get the argument. We are getting a top quality manager who will come in and be the manager we thought he was going to be when he left Brighton.
"I don't get the narrative that we think we are too good for Roberto De Zerbi. It's crazy."