1. I worry that telling him he may have this diagnosis will give him a reason to resist these things even more?
2. Since he is highly gifted, how does this effort (or inability to put forth effort) vs. academic aptitude thing work out through the middle school and teen years?
3. Do I need a diagnosis or can I just have him work with someone (or me) using strategies?
The trick is to really get explicit about the difference between explanation and excuse. The explanation is incredibly important, because he (and you and his teachers) need to really, really appreciate that he is trying to do something terribly hard for him, for which he doesn't have the skills, and where he needs explicit, repetitive teaching of these skills, as well as supports to make up for their absence/ weakness (supports which can hopefully, slowly, be reduced over time - but are essential to start). All of you have to truly believe that he is not lazy, and no, he really
couldn't if he just tried harder.
But that's no excuse. He's got to
own that weakness. He needs to recognize what it is, how it affects him, and that it's
his responsibility to do something about it. He needs to accept that he has to do things differently, ask for help, take longer, etc. It's not his
fault that he is struggling. But it is his
responsibility to do something about it.
With my DS, the avoiding work that's too hard because of LDs has fed a nasty cycle of avoiding effort when effort hurts. The hurt is legitimate, but the avoiding hard stuff is deadly. We're working very, very hard to undo this, and it would be a lot easier if we'd realized just what a vicious cycle this was, a whole lot sooner. Unfortunately, avoidance worked beautifully for him right up to middle school. For years, too many teachers let him get away with not getting stuff done because they knew the work was far too easy for him, while producing the output was very hard. argh. Now, the work finally isn't make-work. It's engaging, appropriate and challenging. And he has no ability to get it done. Yes, it does hurt.
You have to do it anyways. It's your responsibility to work with the adults around you to find ways that work for you to enable you to get. the. work. DONE.
Highly gifted without work ethic is a recipe for trouble. Throw in unremediated LDs that the child has never learned to properly manage, and you have disaster.
You have enough questions that I would strongly recommend a full psych assessment if you can possibly manage it. You need to know where the challenges are in order to address them properly. Sooner is always way better than later. In the meantime though, Smart but Scattered (mentioned above) can help understand what some of the blocks are, and how they can be addressed. As a previous poster noted, good executive function is essential to, well, pretty much everything.