Here are some steps that I am taking with Brito to train a retrieve over high jump; maybe this can help you get started too. I have not yet introduced the stay before the send. I also did not bother with the dumbbell hold in front.  If I were ready to add in the dumbbell hold, I'd have brought his platform back into the picture. Brito knows how to circle an object (I call that "fly").  I warm him up with several "fly" sends. I do this because it allows him to learn to jump both towards and away from me without adding the complication of a retrieve.  Over the next several weeks I will move the location of the cone until he can go both ways over the jump without fail.  Then I'll try it with the dumbbell. I ask him to "fly" with the jump in the picture. I ask him to "fly" with the jump, and I step back so he can jump on the return. On one round he kicked the jump with his foot; that is why you see some reluctance to jump after that. I add the retrieve. The order is dog, dumbbell, jump and me.  All he has to do is jump one way:). Next is dog, dumbbell, me walking over the jump and return.  This is less "enticing" Next I stay on "my" side of the jump but toss the object over when we are both very close.  This makes it likely that he'll go over on the way out.  To get him to come back over the jump, I stay very close. Next I toss it over the jump while sitting on the ground. And finally I stand up straight and do the retrieve. I will not go further with this exercise until he can reliably do a jump/fly/jump sequence no matter where I place that cone.  I need to be convinced that he will come back over the jump every time. http://www.youtube.com/watch?v=Mfa2wSsaiRU