The north London outfit look set to be in the mix for a European berth come the end of the season, but are three points short of fourth-placed Liverpool.
And Sherwood fears a lack of UEFA Champions League football could lead to a White Hart Lane exodus, although he has no doubt the club could attract players of equal calibre.
"It’s always a risk," he said. "But Tottenham are a massive club and will always attract the biggest name players.
"If players are coming here to build and progress with the side, they will pick Tottenham.
"At other clubs, these players will go and sit on bench and pick up championship medals, which is not what I would have done.
"This club sell themselves and are bigger than any manager.
"It’s a massive club, and players will come if they want. They know full well what this club can offer.
"If the be-all and end-all is the Champions League and we’re not in it, they have to make a decision."
Sherwood insisted he does not underestimate how important a top-four finish would be for Spurs, but knows how big a task lies ahead if they are to achieve that goal.
"It's massive for the club," he added. "We all want it, but so do Manchester United, so do Liverpool, so do Arsenal.
"Our target is fourth place, it always has been. If we can get higher than that, great."
Tottenham have not qualified for the Champions League since featuring in 2010-11, and continue their qualification challenge for next season at Newcastle United on Wednesday.
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