Louis van Gaal is waiting in the wings as Daniel Levy runs the rule over Sherwood's reign, while a striker and left back are required following Andre Villas-Boas' emotional exit.
Eyebrows were raised throughout the football world when Tottenham chairman Daniel Levy opted to hand Tim Sherwood an 18-month contract as new head coach earlier this month.
After all, Sherwood had zero management experience and despite being long identified as the club’s next manager, the opportunity arose earlier than expected following the dismissal of Andre Villas-Boas.
While it may have seemed a risk to hand Sherwood a year-and-a-half deal, the 44-year-old is well and truly on trial until the end of the season as he looks to improve performances and results.
If Spurs can achieve, or come very close to, a top-four finish then the former midfielder and his two assistants - Les Ferdinand and Chris Ramsey - will be given the summer to build the squad and start next season in charge.
Sherwood will be given until the end of the campaign, whatever happens, but Levy and the Tottenham board are well aware that a number of potential replacements will become available in the summer.
Chief among them is Netherlands coach Louis Van Gaal, who did indeed meet with Levy in Holland earlier this month, before Sherwood’s official appointment.
Van Gaal leaves his job in charge of the national team after the World Cup and despite refusing to job share the former Ajax and Barcelona coach is extremely interested in taking over at White Hart Lane.
Likewise, Spurs have received encouragement that current Ajax boss Frank De Boer would be willing to consider offers at the end of the season having refused to leave the Dutch champion in the middle of the campaign.
Sherwood has garnered seven points from a possible nine in the Premier League so far this term, asking the Londoners to play in a more attacking style and moving to a two-man strikeforce of Emmanuel Adebayor and Roberto Soldado.
It leaves Spurs, who are targeting a top-four finish, in seventh place in the Premier League at the turn of the year with 34 points, three behind fourth-placed Everton.
STRIKER AND LEFT BACK LEAD JANUARY PLANS
Sherwood feels the Tottenham squad is already bloated, especially in midfield, although a severe injury crisis means resources are already being stretched to the limit.
After signing seven internationals in the summer at the cost of more than 100 million pounds, the club has no plans to spend heavily in January, especially given the problems experienced by the new arrivals in adjusting to the Premier League.
Money is available to spend but Tottenham will likely keep the powder dry until the summer, targeting loan and short-term deals to fill gaps in the squad in the second half of the season.
With striker Jermain Defoe set to join MLS side Toronto for the start of its season in March, the priority is a striker to support Adebayor and Soldado, although Sherwood is a fan of youngster Harry Kane.
One shock target could be former Spurs striker Dimitar Berbatov, but relegation-threatened Fulham will resist offers for the Bulgarian striker, who has six months remaining on his contract and almost returned to White Hart Lane at the end of the 2012 summer transfer window.
The other problem position for Tottenham is at left back, where there is no natural backup to Danny Rose, although Kyle Naughton and Zeki Fryers have both filled in there this season.
Luke Shaw is a long-term target but Southampton will not sell him in the winter window, while Chelsea also wants the 18-year-old to replace Ashley Cole.
Interest in Real Madrid star Fabio Coentrao has all but disappeared along with Villas-Boas, but Tottenham is considering exercising the January recall option in Benoit Assou-Ekotto’s loan deal with QPR.
The Cameroonian was forced out by Andre Villas-Boas but, like Adebayor before him, could be given a fresh chance following the change of management.
There have been suggestions that Villas-Boas was somewhat happy to leave Tottenham, and some have even claimed that the Portuguese coach resigned following the humiliating 5-0 defeat to Liverpool earlier this month.
But that was not the impression Villas-Boas gave after being dismissed by Levy in a meeting at the club’s Enfield training base on Monday Dec. 16.
In fact, poor old Villas-Boas said his emotional goodbyes and - according to training ground sources - spent hours crying in his office.