Children develope. Pleasing the adults around them is one step on the journey... trust me it doesn't last. Soon his desire to please adults will dissapear into gaining the respect of his peers stage... or something like that.

The answer to your question is IMO to listen to him patiently and be there for him. If he's feeling a heavy load of expectations from you that will cause him to close up rather than open up. He'll feel he must tell you what YOU WANT to hear, rather than what HE wants to tell. Give him the space to be himself and share what he wants to share. He'll test you out to see what kind of a reception he's going to get and if he finds that you are interested and listen (without trying to overly correct him) then he'll feel safe and cared about and will share more.

As puberty aproaches he'll have a million questions. Listen well now and be interested and accepting now and you'll get those questions eventually.

Blessings
Cat.