Sherwood played nearly 100 league matches in midfield for Spurs after winning the Premier League with Blackburn Rovers, and rejoined the club as assistant first-team coach in 2008 before progressing through the ranks to land his first senior management role.
Tim Sherwood says the uncertainty surrounding his future as Tottenham Hotspur manager is similar to that of a school supply teacher.
Sherwood has been forced to deal with constant speculation over his job security since taking charge in December, with the likes of Frank de Boer, Louis Van Gaal and Mauricio Pocchettino all linked to the role.
"People will always judge on what I've come in and done," he said.
"You're absolutely right, it's imperative to have a pre-season and bed your ideas in. And also I'm doing it with a lot of uncertainty around my future.
"If you have a supply teacher who comes into your school, sometimes they're not treated with the respect that a headmaster is."
Tottenham head coach Tim Sherwood says his rumoured replacement Frank de Boer would have a "hard act to follow".
Ajax manager de Boer said he was open to speaking to Spurs about taking over amid rumours the north London club had contacted the Dutch champions about his availability.
"What am I going to do? I'm not going to roll up and die, I'm just going to get on with my job, which is to try and prepare my team to win football matches and whatever will be will be," he said ahead of this Saturday's derby against West Ham United.
"I've just got to carry on with my business, show my personal pride and professionalism and make sure that those lads are prepared to win for the team and for the fans and for this great club.
"I don't think he is too interested in looking at what I am doing already because if he did then he would see he has got a hard act to follow."
Tim Sherwood insists he is not affected by persistent rumours about his future as Tottenham manager after his side's 5-1 win against Sunderland on Monday.
Reports that Sherwood would be replaced as manager this summer threatened to overshadow the game, but two goals from Emmanuel Adebayor along with efforts from Harry Kane, Christian Eriksen and Gylfi Sigurdsson helped Spurs to victory.
"I can't affect that. It doesn't affect me," Sherwood said when asked about the speculation.
"I am just professional, I know I have got an opportunity to manage this football club and I owe it to the players and the fans who come and support us to do the job professionally. That's what I did, just got on with the job."