The 20-year-old defender put pen-to-paper on a new six-year deal last month following a successful season-long loan at Brighton.
It was at the AMEX Stadium where Colwill went under the wing of former Reds star Adam Lallana, who advised the promising centre-back on where he should play his football.
Central to the discussion was new Blues boss Mauricio Pochettino - former manager of Lallana's during his stint at Southampton.
And Lallana's seal of approval was enough for Colwill, who was being chased by Liverpool and the Seagulls this summer, to commit his future at Stamford Bridge.
"I have had conversations with Adam," Colwill told The Mirror.
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"And he told me about how much of a good guy he [Pochettino] was and he thinks he is a really good manager and I took that on board when I was making my decision.
"When I finally met him [Pochettino], I realised everything Adam said was true."
Despite Chelsea's indifferent start to the season, Colwill is convinced the west Londoners have the right man in the hot seat and more importantly, the manager best placed to aid his own development.
He said: "He is a great manager, really makes me feel comfortable and allows me to play my best game. I think with him at the club, it has changed so much and now we want to kick on.
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"I think the big thing for me is, on the first day I came in, putting an arm around me and showing me that he respects me as a person and also as a player.
"That allows me to work my hardest and makes me want to play my best for him.
"That's a big difference, him showing that there are two sides whereas the majority of managers may just look at you like a footballer, which he doesn't.
"That helps me play my best football. I know I'm going to improve. I can guarantee that. He's such a good manager and he will push me, he won't let me have any off-days, that's what I need.
"Someone like me, if someone lets me go to sleep, I might just have a good day or a bad day. I need someone there to give me that kick up bum and say 'keep going'. That's what he does."
Colwill recently earned a call-up to the England senior squad and was quick to acknowledge the part Lallana played in helping him reach the level he is currently displaying.
"I am someone who is a chilled person and sometimes I need someone to give me a bit of a push," Colwill explained.
"And at first I did not really understand why he [Lallana] was always on me.
"But then once it clicked in my head, I realised that he was only trying to help me. I was happy and lucky to play alongside him and he definitely helped me."