Sherwood took over from Andre Villas-Boas in December, and a point at home to Aston Villa on Sunday will see them secure sixth spot and a place in the UEFA Europa League next season.
Despite signing an 18-month contract, Sherwood's future at White Hart Lane remains subject to constant speculation, and he remains unsure over what will happen come the end of the campaign.
"I am doing this job with a lot of uncertainty around my future," he said.
"If you have a supply teacher who comes into your school, sometimes they are not treated with the respect that a headmaster is."
Midfielder Sandro reportedly told ESPN Brazil earlier this week that Sherwood was set to leave at the end of the season, and the coach suggested that some of his squad knew more about the situation than he did.
"If I need any information, I am better off asking the players," he said. "Sandro obviously has a knowledge of what is going on. I wish I knew.
"I don't know if the chairman has spoken to Sandro but obviously somebody has told him.
"The players look a lot at the speculation and it begins to be more than that. I have had a lot of players come to me and say to me: 'Our agents have told us you are not going to be here next year.' It's a very difficult situation."
Get the best features, fun and footballing frolics straight to your inbox every week.
Thank you for signing up to Four Four Two. You will receive a verification email shortly.
There was a problem. Please refresh the page and try again.