The Blues skipper has drawn comparisons to himself at the same point of his career – and feels the academy product can be, at times, more valuable coming off the bench in games.
Chaplin, 20, has been used mainly as an impact substitute during his first-team career – a tag he desperately wants to lose.
The striker is vying to retain his place in Kenny Jackett’s side for today’s visit of Fleetwood (3pm) but faces competition from Oliver Hawkins.
The Pompey new boy missed Tuesday’s 3-1 defeat at Northampton following a head injury picked up against Wimbledon last Saturday. But he could return in time for the visit of the Cod Army.
Pitman knows Chaplin wants to play week in, week out because he was in a similar situation as a youngster.
Yet the former Bournemouth forward believes it could be beneficial using the Blues’ prized asset as a substitute on occasions.
‘It’s tough for young lads,’ said Pitman.
‘I know from experience it’s tough to start game after game when you’re that age.
‘Conor will want to play every week because I remember I wanted to do the same.
‘Sometimes starting Conor will be the right thing and sometimes bringing him off the bench when the game is a little bit more stretched will be the right thing for us.
‘The manager knows what he is doing in that respect.
‘But sometimes it is best for the team that he comes on off the bench.’
Pitman succeeded Michael Doyle as Pompey captain after completing his summer switch from Ipswich.
He’s the elder statesman in the Blues’ starting line-up – despite still being four months shy of his 30th birthday.
Having scored 13 goals for Bournemouth in their glorious run to the Championship title in the 2014-15 season, Pitman certainly has the experience and pedigree to wear the armband.
The Jersey-born striker has been impressed by Chaplin’s goalscoring prowess during his Fratton Park career.
And he is enjoying the responsibility of being the Pompey skipper.
‘Conor has definitely got something about him,’ added Pitman.
‘If I can help him, I will help him out. He has got his own game and certainly knows where the goal is.
‘Captaining a team is something I haven’t done before but I am really enjoying it.
‘It’s been a pleasure so far and the boys have made my job quite easy – hopefully it continues that way.
‘I don’t feel as much added pressure wearing the captain’s armband.
‘What I’ve always said is it wouldn’t change how I go about things.
‘If something needs said, I’ll say it whether I have got the armband or not and it’s been alright so far.’