Best time to ask player to reconsider retirement?

Ive got this player whos 37, hes been top league goalscorer for 7 years in a row, hes been declared the best player of the league 5 times, hes not that good now, but he is still extremely important for my team, played over 450 league games for the club, he scored over 260 league goals for us and so on.

I know his not too old because I had Henrik Larson in season 2010/2011 and he was 39 years old, so Im sure this player can play for at least two more years (its 2027 in the game).

So now its start of the season and he declared that he plans to retire at the end of it. What I know from previous FMs is that she should play a few weeks before I ask him to reconsider.

But whats the ideal time to do it? Should I let him play august/september and ask him then or should I wait for the end of the season to ask him to stay on for another year?

I think you should let him go. It's time to let him move on.

Wait till he hits a good stretch of games where he has a good form average, then ask him. He will be confident of his ability at that point in time so he might reconsider.

I think you should let him go. It's time to let him move on.

Why do you think that?