Ds1 is 14, and in yr 9.
In yr 7, he did need some support in organising his homework, and a wee bit of badgering - it was a sea change for him. he was bewildered. I did despair a little - this is a child that left for school one day, meandered down the street, tracked back, then knocked on the door, cos he realised suddenly that he hadn't put his shoes on... It seemed so effortless for everyone else - am sure it wasn't though!
In yr 8, it was much less so - he was catching on, and getting into the swing of it. He knew if it wasn't done, he would have the consequences from his teachers, but it was still fear of getting into trouble that motivated him. He also got an alpha smart keyboard for his mild dyspraxia (which affects organisation and planning skills too). This year was just really me reminding him - again, I really noticed the difference between yr 7 & 8.
Now in year 9, he completely organises himself, and what motivates him, is doing well, rather than consequences. He hoofed it off to revise biology the other week, came back, and asked me to test him, I did, he realised he was not as strong on the endocrine system, hoofed it back, revised again, and asked for a few pointers (am an endocrinology nurse) asked me to test him again, and he did really well!
We've gone from 'can't do, won't do' in yr 7, where I had to lash the whip a bit, to 'will do but only cos I have to' with reminders in yr 8, to 'want to do well, will ask for help if I need it' in yr 9.... Go Figure!
Am generally of the tendency to let them get on with it, with an eye kept out for problems, general encouragement, a bit of monitoring etc...