Here's a post I made on my forum about asking permission. I hope you can find it helpfull

I agree with all the replies except for the "limit the small talk". Sorry soccerref but I feel the more they know about you weather it's small talk or personal, the better off you are. I've stopped and asked people that I can just tell they're not going to let me hunt but still got it because I found something we both had in common. Starting talking about their dog, their garden! anything but hunting. Now if they're short with you and you can see they don't want to small talk then I agree with you. I feel I've gained more permission to hunt with small talk than just going up to the landowner and getting straight to the point. Remember, you're asking them to allow you to walk around their property with a gun! That scares a lot of people so again, the more they know about you and can relate to you, the better off you are.
Being able to read the person is the biggest part of the game of getting permission beside being polite I to like to take along this form I made out in trying to get permission and it works like a charm! Another thing you might want to keep in mind if you feel they're leaning towards saying no is limit what you want to do. Again, I've come across people that tell me, "well, we don't like the idea of guns in our woods because we walk around a lot". That's when I tell them I'm only looking to bow hunt and then explain my shooting zone with a bow. I'll end up getting permission to bow hunt only on the property which is fine. I'm now at least in the door and have plenty of time down the road to build a hunter / landowner relationship. I've done this three times here in NH and I now have permission on all three pieces of property to bow and gun hunt! If you get permission to hunt! stop in from time to time in the off season to say hello or just to small talk with the landowners. Keeping that hunter / landowner relationship going even in the off season will go a long ways
If you're having a hard time getting in touch with the landowner never ask for permission to hunt over the phone! It too darn easy for them to say no! if they don't see you in person.