An honest Sherwood said he expected to see "a little more gut, a little bit more pride, a little bit more feather-rustling" during the second half of his team's 4-0 loss at Stamford Bridge on Saturday, after again watching Tottenham capitulate against one of the top four.
Tottenham are 6/1 with Bet365 to finish in the top four
"It's a different era now," Hoddle told Sky Sports.
"I agree he was very honest but personally that's something you say in the dressing room to the players. You might come out and disguise what your feelings are.
"Management is about when things are going wrong. When you're playing well and winning it's easy to be a manager of a Premier League side."
The loss was a huge blow to Tottenham's chances of qualifying for the Champions League, with fourth-placed Manchester City four points clear of them and having played three fewer games.
Former Liverpool and Tottenham defender Jamie Redknapp praised Sherwood for his honesty.
"In a way for a lot of people, that is refreshing because he's probably saying what every Tottenham fan thinks tonight," he said.
"It's very easy to turn around and say 'we did all right and needed a bit of luck here and there', but he was just honest and straight down the line.
"People are talking about Tottenham having to get into fourth if he's going to keep his job. I find that absolutely ridiculous.
"They have finished fourth twice in the last 23 years, so what makes them have a divine right to finish fourth this year?"