You should stop prior to making contact with the trailer in order to check the height compatibility. (I believe that this isn’t strictly necessary provided you can see from the mirrors - which you probably can). I always teach to stop, get out and have a look.
From there, no need to get out again.
Sounds like you’ve got a nice truck; presumably a good instructor to match who I am sure will be able to clear up any worries you have.
Hope this helps, Pete 