Sit in the drivers seat and have your co-pilot walk to the rear on each side. Have her signal to you when she is several feet past the rear of the trailer. Get yourself a reference point of view in the mirror for safety factor. You could even do it in the street with a parked vehicle for better reference. As stated, experience is a great aid. Some people have installed back-up cameras and that will also give you a reference as to when it is safe to move over.
Good luck.
Edited: p.s., having your side view mirrors adjusted correctly is a big, big help. To many have them turned in and see the side of the trailer. I typically turn my head to look at out the mirror and when I do, that is when I seed the side, and just barely. For several years my mirrors have been electric and I adjust them accordingly for backing, and then back to what I stated for driving.
And the person walking back toward the rear will also let you discover your blind spots.
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