I re-watched this a few times yesterday, while I was home form work nursing a cold. The beginning line of questioning to Dolores, about answering questions correctly so they can wake up from the "dream", was done by Jeffrey Wright's character, but differs from the line of questioning we witness later. It plants seeds of discontent: "What if I told you the newcomers were there for you to play a part" etc. I don't remember the exact phrasing but it was along those lines. I think Jeffrey Wright's character is the one sabotaging the hosts, planting seeds of memories or discontent/rebellion especially when paired with him whispering in Dolores' father's ear before he was put in storage. I can't yet guess his motivation but it may be working to oppose whatever "higher stakes" Westworld is really about (human army, spies, who knows).