The England legend praised Lingard for his fine loan spell with the London club, but suggested he lacks the same attitude as 'ultimate professionals' like Harry Kane and James Milner as he appears happy to wait for his next career move.
Lingard departed Old Trafford this summer upon the expiry of his contract, ending a 22-year career with his boyhood club having joined their academy at the age of seven.
Now without a club, the 27-year-old was widely expected to rejoin West Ham on a free transfer in time for the new season, but a move is yet to materialise.
Lingard was linked with a move back to the Hammers and with a switch to newly-minted Newcastle in January, but it is claim his wage demands proved a stumbling block and he ultimately stayed with United where he started just four games last season.
That is the biggest shame for Pearce, who hates to see talent wasted on the bench.
The former defender, who left his role as a first-team coach under David Moyes at the end of last season, is a big fan of Lingard, but has been left disappointed by his current situation and has urged the star to get his future sorted quickly.
And he hopes that it will see him return to West Ham.
"I wouldn't say Jesse is struggling to find a new club, it's more that he's struggling to get his head around where he's going, and I think he's probably asking for a little too much money," Pearce told talkSPORT Breakfast.
"Speaking from experience of working with Jesse, he's a fantastic kid to work with. Physically very good. He hadn't played much football when he came to West Ham, and he was one of the fittest when he arrived. He's naturally physically talented and he works hard on his fitness as well.
"A great kid to work with, he was wonderful for West Ham and I'm just a little bit disappointed he didn't think to himself, 'I need to be hell bent on getting back to West Ham'.
"He seemed to be really enjoying his football at West Ham, he enjoyed the environment, he enjoyed the people around him. He's a good boy and great to have around the building, he always had a smile on his face.
"If I was in Jesse's position, or any player in his position, he hasn't played a lot for Manchester United and was out of contract, I would want my next contract with a new club signed and sorted before I become a free agent.
"Then you can walk into your new football club on day one of pre-season, not wait and enjoy the summer and pick up somewhere further down the line - you've missed pre-season by that point.
"That's the thing that disappoints me, when I see good players sat on the bench and not playing football.
"When I look at Jesse's last year… I come from a generation when you wanted to play every week, you're hell bent on it and you didn't want to miss games, whatever it took.
"There was never a financial decision in football for me, it was always a football decision. When the time came for myself to stay at Nottingham Forest and not elsewhere for more money, because I was happy with where I was working - that was the main decision."
"I agree," added Breakfast co-host Trevor Sinclair. "I can't understand how you're not driving yourself to play week-in, week-out. Because if you're not playing, what are you doing? You're training every day to then just go to a match, watch it from the bench or the stands and then go home."
Lingard's future has been the topic of intense debate on talkSPORT this week, with opinion split over the midfiedler's attitude.
Outspoken pundit Simon Jordan said the 27-year-old has 'flushed' the last three years of his career in favour of a pay cheque, having seen out his Manchester United contract rather than pursuit a move away for more regular game time.
He also insisted he will be more remembered for his videos on TikTok and dancing celebrations that his achievements on the pitch, which led to a strong reaction from Gabby Agbonlahor who branded the former Crystal Palace owner as 'bitter'.
Pearce wasn't afraid to take sides in the argument, and again admitted his disappointment that Lingard hasn't pushed to achieve more with his undoubted talent.
"I actually agree with Simon," he said. "I think he was very factual and fair with what he said. I like Simon, I like his forthright statements and I agree with him here.
"Anyone can come on and have a halcyon 15 seconds of fame, but the ones who I really respect as players are the ones who are maybe not blessed with so much ability but who maximise their potential. That's all you can ask of any individual.
"Harry Kane - I think he has maximised his potential. I watched him as an England Under-21 manager and I thought, 'Hmm, I'm not sure if you're going to help me out in a year or so'.
"I didn't think James Milner would get senior international caps when I was working with him at Under-21 level. A brilliant lad, a great professional, but he has maximised his potential and got 40-odd caps.
"These players, James Milner and Harry Kane, have got my utmost respect because they have maximised every ounce they have got and are the ultimate professionals.
"I still think what Jesse Lingard has done on the football pitch outweighs what he does on social media, his football has been good enough and he's represented England.
"I don't think TikToks or social media stuff really matters to managers in this day and age, what matters is if the player is fully committed to his profession and to being the best he can be."