Last Saturday, Javier and I were off to John's place. Upon arrival, we met with Rom (Yang) who was there also to train with us. I trained against John while Javier trained against Rom.
Usually, in casuals and training sessions, I don't challenge a person's weakness. There is a time and place for that I believe, and that is a tournament setting. As for casuals and training, a person should seek their opponents strengths and challenge it. If this person has very good blocking try to break through his exceptionally good blocking. If your opponent has the ability to tech very well challenge his teching abilities (and so forth). The idea is that you will, in time, absorb your opponent's strength(s). At the very least, you will be able to observe your opponent's strength(s) and apply it to your game-play in whatever possible way you can. I know it doesn't make complete sense but if you notice something that another player does exceptionally well (be it block strings, ect.) try to apply it to your character/game-play. That person could be using C.Viper while you use Ken, but the idea is to be open-minded and use what you see from other characters and attempt to apply it to yours. If it doesn't work out then that is okay as well. At least you attempted to explore different options and different mind-sets with your character.
For example, I did not go into the session against John doing crazy gimmicks or setups. I challenged, what I believe is the best in the game, John Choi's low forward. Air has told me the exact same thing when he played against John Choi. Air explained that John Choi's usage of low forward is one of the best if not the best in the game. I believed him since I had played him many times in the past.
Several months ago, I would challenge John's low forward and struggled very much. I forced myself to throw fireballs to keep up with John. At the time, my fireballs were terrible and I got destroyed. However, recently I challenged his low forward and I was able to make a stand for myself. I challenged every pixel of both health and spacing with low forward. If I failed to make a stand against his I would get back up and try again until I got the spacing correct. Within time I felt my footsies improve physically and mentally. It has also given me much confidence in my character to walk up and stick out low forward appropriately.
I ended up splitting 50:50 with John (who used Sagat, Guile, Ken, Guy, Ryu, and Juri on me). He also mentioned that the last time he played was this year's Evo. For him to challenge me, who had been practicing just about everyday, in fundamentals and footsies tells you that it is so natural for him to have that mental spacing and intuition of shoto characters. Giving the benefit of the doubt, he had several execution errors and hiccups in his game-play. That, however, did not stop me from challenging his strengths. :)