traying to coach! I need help

I started coaching a 15 years old boy, who has not so good but decent times, I want him to be able to break at least one of his “age-group” records from our club. Since I write his workouts, I wonder which record might be the closest one to shoot for. Event SCM........ His time...........club´s record 50 free............30"41............25"52 100 free.......... 1'05"............ 56"75 200 free......... 2´26"16......... 2´10"20 400 free......... 05'02''68......... 4'36"95 800 free.......... 11'17"04......... 10'12"91 50 *** ..........40''23.............33"06 50 back ...........36"09 .............29"52 100 back......... 1'18"54 ..........1'03"66 200 back .........2´43"35......... 2'17"56 100 IM............ 01'15''96......... 1'04"22 200 IM............ 2'46"24........... 2'21"56 400 IM ............5´54"16.......... 5'00"03 I think I will try to make him focus on freestyle, his closest times to the record (very far BTW) seems to be the 200 free and 400 free events What do you think? I also want to know if his times have a "normal" relation; I mean, he probably can go faster in the 800 free from his 400 free time. And faster 200 IM from his 100 IM time. Im use to make workouts for myself but I know how far I can push myself... This is new for me, so Im trying to test him, 100's reps, crazy long sets, crazy hard sets, and Im looking forward to his "never done" 7000 meter workout :angel:. He seems to enjoy challenge, I need some feedback about his times and tips for training 15 years olds. thanks