The 36-year-old hung up his boots in November after his contract with former club Burnley expired.
He came through the ranks at Leeds United and also went on to play for Tottenham and Everton.
Lennon later had a short stint in the Turkish Super Lig with Kayserispor, but he will forever be remembered for his time in the English top flight.
The former winger gave an honest assessment of the gaffers who have managed him in the past and waxed lyrical about a certain boss in an exclusive interview with talkSPORT.
Which of your former gaffers gave the best team talks?
"I am going to say Harry Redknapp," Lennon told talkSPORT.
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"Just very simple, and I only liked him because he said give the ball to Hazza [Harry Kane] and Luka [Modric].
"Give it to Harry, and Gareth [Bale], get the ball to Luka, get it in the box and Jermain Defoe or Benty [Darren Bent], maybe not Benty, they weren't best of pals.
"He was very simple, and like I say, any manager that says give the ball to me I was happy with.
"Sometimes he would come in pumped up, but most of the time it was like get the ball out wide, and into the box, let's be aggressive."
Who go involved in training the most?
"I think the only one I have seen get involved was [Mauricio] Pochettino.
"He was involved in the middle when we used to do the boxes and stuff, and fancied himself a a bit of a player. He joined in especially at the beginning of the session.
"I think he thought he had it more than he actually did [on his skills]. I did not have much time with him, but he changed the whole demand on the club.
"One thing I noticed straight away was how fit he wanted his players to be, so that changed straightaway.
"We changed the days off system, so we was in most days of the week, but attention to detail also, he took us up to another level with that, with his tactical stuff.
"I think it is tough for him [at Chelsea], I really do. They have so many new players, young players, but I do believe he is better with younger players.
"Though if he is going to do it, I think it will take a good long time. The expectation of Chelsea, they expect to win every week, no disrespect to them, they have good young players.
"But you can see they are a long way away, he is already talking about getting new players in January. Look at the squad list already, how do you manage all those players?"
Angriest in the dressing room or on the training pitch?
"I am going to say Sean Dyche, I seen him lose it a few times. He can lose it!
"Full on rage, not happy, literally calling people out, but yeah he is a big lad, and scary man when he is in full flow.
"There was an odd time some of the lads might pipe up, and have a little go back, but that was the type of group Burnley was.
"There was some big characters there, and he did not mind it. He said he was not one of those managers where he could not say 'no' back to him.
"He would take you on, head on. Then he would shake hands with you after it.
"You could have an argument with him, then the next day it would be forgotten about."
Who made you the most nervous?
"Fabio Capello just had this thing about him. I remember walking into the England camp for the first time.
"I remember him just looking at me, and I was thinking what is going on?
"He just had this aura about him where you felt you was not sure and felt awkward around him."
Favourite ever manager?
"I have to give it to Andre Villas-Boas. I really enjoyed playing under him.
"I thought he was not just the best man manager, I thought his training sessions where unbelieable.
"He gave me that real freedom, I felt he was one of the most managers who gave me the most on the pitch.
"I remember going to England and speaking with the Chelsea boys, and they absolutely hated him.
"It is different for every player, because you might hate a player that I liked.
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"Everyone has a different story, but for me, even the way he got ther group together, not just the eleven, he literally took care of everyone in the dressing room.
"Even the way he spoke with staff members, anyone in that club, he was the best man manager I have seen."