I think if you want him to go on both the pee pad and go out side, you need to work on one at a time. Once he gets the first one mastered, then you can move on the the next.
Since you are a shift worker, I think I would work on the pee pad first. This may be difficult, now that the weather is getting warmer, but do not let him out until he uses his pee pad. Then he gets to go out. Put a dab of his pee on the pee pad and this will help him understand where he needs to go. Hope this helps!
