Hobbling is not difficult and the horses pick it up very quickly.
The first time that I hobble a horse, I make I can keep him under my control. So I usually leave a lead on him and put the hobbles on. If the horse doesn't move on his own, I will ask him to move a few steps by pulling on the lead rope. Make sure you are clear, as they may stumble and lunge forward as they learn. If they get excited, I have the lead and stop any further movement.
I almost alway intro hobbles when the horse is hungry and standing in an area of lots of grass. So their motivation is to eat, not run off. Once I'm comfortable that the horse knows he is hobbled and is more interested in eating, I remove the lead and let them just graze, They will experment with moving in the hobbles as the search out grass. I am fine with them just hoping around, What I don't want it paniced race across the meadow.
Using just the standard two front legg'd hobbles, You horse can still out run you, But they tire quickly and won't go far. A 3 legged hobble will secure the more adventuresome horses.
The biggest problem with hobbles is rubbing the leg and causing sores. Never use nylon rope for hobbles. I do use the occassional nylon flat belt for hobbles. Get them in the wider widths, 1.5" to 2" wide. Prefer a wide leather strap.
A large soft cotton rope makes a good hobble. Watch fleece and other very soft materials as they collect burs and foxtails etc that can rub inside the hobbles. I prefer the leather because ot doesn't collect burs.