It sounds like it may just be a matter of experience, as far as knowing range/distance. Also, the things he does to get inside...I think you have to know what they're worth. You slide in behind the jab, or slip a punch to get inside, it might only lead to one or two punches, then it is time to get out. Not to stand in hoping for more, getting tied up and wasting energy in clinches. Just to make the initial move, be sure of the initial counter, throw the punch behind it, change the angle and start again.
At his stage- 4 fights?- I would be looking to make sure that he is sharp at those initial slip and counters (maybe a couple punches) then getting out. Then build on it, throwing more punches when it is natural to him to land that first one, then change the angle, then look for more. Tell those guys to keep holding him in sparring. He'll learn that there are ways of dealing with that- first and foremost being to land something on the way in and then move and make him turn.
Last, watch him train, hitting the heavy bag and the mitts. If he is falling in a lot and smothering himself sparring, he's doing it there too. That is something that is easy to correct in the ring with the mitts, you just have to break those moves down and really watch his feet.
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