My young one learned most of his stuff on
trail. I ponied him with an experienced horse, did everything I could
think of while ponying him including voice commands. Then I rode him with
the experienced horse. Then I rode him alone. I also took my time,
probably the first time in my life that I was not in a hurry. All the
stuff on trail that he experienced just built up his knowledge as well our trust
in each other. So do whatever you are comfortable with.
Jeanie