The 19-year-old was handed a first senior start in the 3-3 draw with QPR on Tuesday by the man that oversaw the development of Harry Kane and Ryan Mason while youth team boss at Tottenham.
And it is the optimism that new Villa Park manager Sherwood brings that helps young players emerge according to Grealish.
"Tim Sherwood gives every player a huge boost of confidence," he said. "I thought I was OK but I feel I can contribute towards the end of the season and play better.
"The positivity around the training ground is brilliant for the gaffer and brilliant for us. It really helps on match day. Hopefully that will come into play towards the end of the season.
"Playing my first game is probably the highlight of my career. To start for my boyhood club was a dream come true.
"You can see what he did at Tottenham with the young lads, bringing them through, just the way he is around the training ground, he is a great guy.
"He's given me my first start in a crucial game which I'm really grateful for. When you're not playing you get down, that's football, you have to stay positive and good things come your way.
"He's done little stuff like bring the younger lads to come and train next to the first team, which is so little but means so much to the younger lads.
ACTION
Jack Grealish is aiming to become Aston Villa's next starlet
"He's so positive around the place, gives everyone a boost which you can see in people's performances like Christian Benteke and Fabian Delph."
Benteke's hat-trick ensured Villa still have a three-point cushion above the drop zone ahead of Sherwood's trip to former club Tottenham on Saturday.
"We know what Christian is capable of, we see it every day in training," said Grealish. "When you have Christian in the team who can score goals in every game we can be 100 per cent positive we will stay up. I'm that sure."
The positivity around the training ground is brilliant for the gaffer and brilliant for us
Jack Grealish
Invalid email
We use your sign-up to provide content in ways you've consented to and to improve our understanding of you. This may include adverts from us and 3rd parties based on our understanding. You can unsubscribe at any time. Read our Privacy Policy
Villa were 3-2 down on Tuesday until Benteke completed his hat-trick in the 83rd minute to salvage a point. Grealish also had his moments during the match to score his first goal for the club he joined as a boy.
"Hopefully it will come soon," he said. "I nearly had it against QPR but obviously it wasn't meant to be. The main thing was the result which was a heartache.
"It feels like a loss in the dressing room. But we have to be positive going into Saturday.
"I found out I was playing on Monday and I've been happy ever since. A few nerves started to kick in towards kick-off but I just see it as any other game. I've played football all my life. I tried to go out there and be as calm as I could.
"You're only doing the same thing as at [the training ground] Bodymoor Heath, just playing football. I just try and stay as calm as I can and do what I do best."
