To get this achievement you need to talk 40 times with the old man at the start of the game.

Every new screen that you reach will add 2 - 3 dialogs. That means if you jump up to the start of location called Great Frontier. Thats the location with these 3 tower at the end I will be enough to complete the achievement. Then jump down and stand in front of the old man. He will say something and then fall asleep and then he will wake up and say somerhing again. You will need to wait for him to say something 40 times.
The 40th time he will start singing or something like that. That means it was the 40th time and you have done it. You got the achievement.

If you need me to do other guide on other achievement let me know. I have over 120 hours on this game and I am only missing 7 achievements in this game.