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How can i help my horse develope the right headset?

I've been working with my horse on dressage for a while, just our little stuff we do inbetween the days that we're jumping. I've used draw reins on him to help him learn how i want his head to be, and how he should know when i want him ot tuck his head in, and arch up his neck. He does however, poke his nose out a lot, and then after a while he'll just lose everything.
I've just recently started my friends horse on the same exact work, but her horse goes right into it, and holds it in the exact position, does it have to do with training, the horse, the bit? Is there something else i could do with my horse to teach him to bring his nose IN? I use a kimberwicke with him, i might be switching to a doulbe hinged kimberwicke with a Copper Roller.

Next time could you please indicate the discipline that you are wanting to do. I have to assume 3-day eventing and you are wanting the "correct" headset for the dressage phase.
Firstly you are expecting that this horse knows what you are asking or that you are even asking correctly. From your statement it appears that he gets his headset for a short period of time, hence I would assume that you are somewhat communicating correctly. However that is only the case if it is achieved through light contact and please no sawing on the mouth.
Secondly, your horse is not a machine where you insert $0.25 and it goes around. You obviously have assumed that all the correct muscle and tendon structure has been built for him to have the correct headset. Yet you state that he likes to poke his nose out, which would indicate to me that is his preferred headset. He holds what you want for a bit, then loses it more and more as you go along. You are expecting that he is a machine, the muscles and tendons must be built up over time, they can not be forced past that point of exhaustion. It is the same as someone starting Yoga today and being expected to do everything right away and hold the positions for extended periods of time. You would have sympathy for them and not expect them to do it perfectly, so what is different with your horse? Rome was not built in a day and working with horses takes time as well. They are not machines.
Why are you changing bits? Why does your horse need a kwimberwicke? Your quest with horses is always to try to get them as light and responsive as possible. Achieving that is through lots and lots of flat-work and educating their mouths in order to be able to have the horse response in nicer bits.
In regards to draw reins, most of the time they are not used as originally intended. They are to use as an aid to the reins to put additional pressure on the mouth to encourage the horse to change it's headset, which can take time. They however seem to get used to force a horse's head into a position and hold it there. Imagine what you would do if that happened to you? You would move your head to that position (like being punished) and when the pressure came off you would go back to that comfortable position. Instead with the draw reins, encourage them to move their head into position a bit at a time and when they move their head towards the goal that you want, hold that there for a while and then relax the draw rein to see if they will hold it there for a couple circles, etc, without the artificial aid creating that headset.

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