Peg down one side, insert the poles, grab the other side of the tent, walk back and stretch the canvas until the poles are upright, Peg the other side down. You might want to have a a rope to the top of each pole to help with this. I usually have two ropes to each pole to help as wind braces anyway so this should work well. The wind braces can be anchored at the midpoint of the tent so they don't wind up being "drunk traps".
By the way, drill holes in both ends of the poles, that way if the peg gets broken out of the pole at one end you still have a place to put the peg on the other end.
Many Klatch