A while ago i remember asking if i could recieve the henchmen items without actually having to run around with them. And i believe bj here told me it didn't work that way.
NOW, i just tried to talk with tomi, had to hire him first of course, but i was high enough lvl to talk through the whole conversation and since i had the item he needed he gave me his ring. Wanted to test if this worked on the others as well, so i went to trade of blades, talked to boddyknock or what's his name since i had his item too, and could finish the whole conversation to give me his ring too.
So i think if you want their items and not their company, you just hire them when your lvl is high enough and you get the item. Blablabla and you can get a very nice item for free, most items boost your stats i believe.
This was new for me, so don't make fun of me if you'd already figured this out ages ago.
normally you have to go through a whole shitload of conversation, over a few level ups to get to the point where the quest item is made clear and to the point when the henchman will actually recieve it. interesting if you can get everything like that..and it will be interesting to see if you can do it in the later chapters when the items get more powerfull.