The German playmaker has been marginalized since the arrival of the club's new manager and is after clarification on his future as former club Schalke shows interest in a loan.
The German playmaker is unsure of where he sits in the midfield pecking order and will meet the Spurs boss in January after featuring just twice in Sherwood's first five games.
Holtby and his agent will meet with Tottenham representatives to discover whether Sherwood has faith in him, before deciding if it is in his best interests to push for a move away from White Hart Lane in the winter transfer window.
Holtby moved to the club in Jan. 2013 but has seen his playing time diminish since Sherwood replaced Andre Villas-Boas, who was relieved of his duties as head coach in December.
It is understood that Bundesliga outfit Schalke is looking at the possibility of bringing Holtby back to Gelsenkirchen, as the club expects Jermaine Jones to depart in the winter window.
Holtby played 89 times for Schalke over the course of three seasons and Jens Keller will look to loan the 23-year-old until the end of the current campaign.
Schalke sits seventh in the German top flight, four points off Borussia Dortmund in fourth.