Let his head of year or tutor know this is an issue so they can start helping him straight away. The SEN department may also get involved.
Make a checklist of things that he must have each day and laminate it so it stays intact. Blue tac it somewhere visible - where he will see it every day in the morning- perhaps inside of the front door. He can use it to check that he has what he needs for that day.
Give him a foolscap folder to keep pieces of paper that he needs, this could be letters he receives from school, homework that is on loose worksheets or pieces of paper. He needs to get into the habit of putting things into the folder as soon as he gets them, both at home and in school. You can ask to check the folder.
When he gets his school diary/ planner make him sit down with you and fill in the dates at the top of each page. This will make it easier for him to fill in the correct week. Often disorganised students record their homework on whatever page they open their planner on, meaning they never know what is due. Many of my students have a sticky post it note/bookmark thing that they use so they can go straight to their current week.
When you get his homework timetable fill in the subjects that will be setting homework on each day, all he needs to do then is fill it in as he gets the homework. You can then check his planner daily and say "DS you were supposed to have science homework where is it"
Encourage him to highlight, tick, cross out homework tasks as he has completed them in his planner. This makes it easier to see what he has done and what needs to be done.
Reward him for using his planner successfully and clearly. This is a skill he needs to learn. I have photocopies of students planners that are organised and up to date. Ask if his tutor can show him a well used planner. Even give him a photcopy to use as a template.
Ask for two extra copies of his timetable - or photocopy them yourself. If he has a locker put one on the inside door of his locker. Put the other one somewhere visible at home. If he leaves his planner in school you can still check what lessons he has.
Make him a mini timetable - double sided as small as is legible. Laminate it and stick it on a key ring. He can keep it with his locker key so he can check what lessons he has even if he has left his planner somewhere. I sometimes make a laminated reminder for students that is the size of a credit card that says " Take to every lesson my exercise books, pencil case and planner" Or you could make on which reminds him of eqiuipment he will need on different days. e.g Monday and Friday PE Kit, Wednesday D&T apron, Thursday flute. They keep these on their keyring.
Check what is available on the school website, I always put on spare copies of homework instructions for my students, there may also be important notices and perhaps his timetable.
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- brilliant, academic brain, but would forget his head if it wasn't screwed on!