Often times people underestimate the power of a brisk, 15 minute walk once a day. I would start by handwalking the horse once a day every day on a flat surface in a straight line and really walk, not doddling. Bring a dressage whip to encourage him and walk as fast as you possibly can for 10 to 15 minutes for the first few weeks, slowly bump him to 30 minutes, plateau for a week, work to 45, plateau and then an hour. At an hour of walking where he is staying comfortable for the whole work out (of course you will have to start varying intensity along the way) then and only then would I begin any trot or hill work but not both on the same day, and with an only walk day in between. I would start riding hum at this point, only on some days. On the trot, hill or riding days, only work for 30 to 45 minutes and not at full walk intensity.
Avoid circles and trying the head down. Listen to the horse and he will tell you when he's had enough. You want to work him to about 80% of his limit, every day.
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