Honestly, I don't really get it - some explanation might help.
I guess you have to start in the center, and can only select skills adjacent to already selected skills. Is there a difference in the skills in the square centers and the square sides, or why are they bigger?
Generally, I like the idea of random skill maps. You won't make a AAA title with 100+ hours of content like Skyrim, so you must go for replayability. In my opinion, you have a higher replayability when you have to rethink your character development each time again, instead of playing your standard characters, thus random skill maps are good.
However, I see problems in the playability of your skillmap representation. In a game like this, I would either only check the currently available skills and select the best one (which would work), or plan the whole character development in advance, and trying to stick to this plan. Here is where your representation is weak: you have to click on every single skill to get its description, and when you're done, you're most likely confused. A graphical representation of the skills would help, maybe with some generic icons (e.g., shield +2)?