I started a new chore chart a few weeks ago. It's a "family" chore chart. Everyone is assigned certain duties to be done every day for a week and then it rotates. This way, for a whole week we are all doing the same thing each day. They must do the chores right after school and I say "to get it out of the way and done with, so you can move on with your afternoon". So far, so good. I even have a checklist with each day of the week listed under each of our names. At the end of the week, it'll determine how much allowance they get. Although, I'm not giving them the option of "skipping" days right now. Unless their specific chore is still considered "done" from the day before.
This week, for example, DD (14) only has to make sure the bathroom upstairs is clean (and I made SURE to list every detail of what CLEAN entails, otherwise she'd swipe through and then say "welll, you didn't SAY to do XX, too) & she also has to make sure the upstairs hallway is clean (vacuumed, etc). She's got an easy week this week.
What just killed me was the first week we started this, I gave myself the dishes & laundry because those are the 2 things she gripes about having to do. So, i figured I'd be a nice mommy and give her a break from them. First thing out of her mouth: "can I have the dishes & laundry next week?". OY. She's going to give me a lot of gray hair.
We've tried other ways and this seems to be working the best. I haven't had any of the issues we had before with her getting chores done. Maybe because it's more clearly outlined now? I'm not sure what it is, but I'll take it!
Good Luck with whatever you decide to try with him. I know how frustrating it is!