Thank you,Arran, firstly good luck and stay safe. I would much rather a lad in any profession come to me and say I am not confident, or I need more training than trying to pick up the pieces after.
Assuming you have your own transport, bike, car, moped? See if you can drive all of the likely routes first, I remember my driving instructor took me some weird and wonderful routes, at the time I had no idea why, but when it came to my test I remember coming round a bend and remembering there is a massive hill here, so I was in the right gear before I went up.
Could another member of staff let you sit on or visa versa on the first round?
as @Exfarmer says, a 15t trailer can push you around, just take it slow and steady.
What area are you in, there may be some local knowledge on here?
Bon Chance.
Area is Leckhampton Gloucester...am doing it for Hartley farms