I'm consistently asking questions with my trainer during lessons and usually have weekly meetings to discuss continuing further and what to do to improve. Plus my trainer and I text outside of the farm all the time.
I think to progress you have to meet several trainers. So that's pretty common to be in a new step in your ride and some of them need a new trainer, sometimes just because your old one doesn't have something new to teach you :)
I'm trying to have the most healthy relationship as much as I can. So when I'm getting upset for whatever, I'm telling him, and he does the same. I'm telling him how I'm feeling and ask him as many questions as I have :)