Charlie Pye of Royal Leamington Spa in the county of Warwickshire wrote to Aston Villa CEO Tom Fox in February before Sherwood was appointed.
While the former Tottenham manager was eventually selected to take over the Premier League club, Sherwood was magnanimous enough to congratulate the young fan on his application, while revealing Charlie had only just missed out on the job.
Charlie's letter spelled out why he would be a good candidate to lead Villa.
"I think my team talks would be very good and my tactics would be excellent," he wrote.
"We need to stop the goals by getting in the way. We need to score more by shooting on target. This is a winning formula, so my dad says.
"As for payment on taking the job, all I ask is for a signed claret and blue football, a WWE wrestling figure and some sweets. As a win bonus each week, I would want a Twix.
"I would appoint my mum and dad as assistant managers so they can drive me to the training ground each day. My mum is also very good at making bacon sandwiches for the players if that helps.
"If I am successful, I would also need you to tell my school that I don't need to attend anymore as I have a job."
Sherwood was impressed by Charlie's credentials, while letting him know how close Fox had been to going in another direction.
"Hopefully you're not too disappointed at missing out and I'm informed that I just managed to pip you to the post so you were very close to being offered the job," the 46-year-old wrote.
"Our chief executive Tom Fox has informed me that the club would like your permission to keep the letter on file 'just in case' - although I'm hoping I will be successful at this great football club."
Having received Sherwood's letter, Charlie told Villa's website: "I never expected a letter from the manager but I was absolutely delighted to get one.
"I was really happy when he got the job because of his passion and I love him even more now. I think he will do brilliantly for the Villa. He already is!"
