Has your plebe set up a semester schedule noting all graded assignments so they can track how busy they will be week to week? Tying mine into outlook was the best habit I took for time management out of the Academy. Not only did I know due dates, I was also able to block out periods I knew I would have obligations (practice, class, travel for games, etc.) and see it visually. It helped me plan on my weeks better and take advantage of free time (aka the weekend generally) to get ahead of work so I wasn't overwhelmed during the week.
If they don't have this set up, have them set it up. Most Corps squaders have to do this, particularly if they're involved in any of the RS programs, already and I'm sure you've seen a copy of the excel version that floats around that should be a blank semester with day 1/2 designations and holidays/football games noted on it.
Next step that could be helpful which my company utilized as well was, if you are doing any kind of weekly report as a TL for your plebe up that involves them reporting grades, have them also include what graded assignments they have coming up and a note in it whether they have started/feel prepared to handle the material. It serves as a trigger more for them to be looking ahead, realizing they're going to have to tell you their progress on events, to start planning.
Different resources/thoughts to think about:
-Depending on the sport, their team probably has academic tutors available as well to utilize during study hall periods and during off hours that may help besides AI.
-Ask them if they have a teammate (i.e. upperclass) that has gone through the course that they trust and was good at the material. I had two teammates I would always turn to with questions (actually brought problem sets to practice at times) when I was stuck. Saved time because I didn't have to go find these people, they weren't going through the material at the same time so they already had a clue of what was going on in the class and had done extremely well, and they had a vested interest in helping me because we were friends on and off the court as well making sure they didn't lose a starting player to the line up (yep that almost happened before nationals although that was because of swimming. I hate swimming still).
-Find your old notes, quizzes, WPR's, etc. for the course and give them to the plebe. If you don't have them or they aren't as helpful as they could be, find that smart classmate in company that you know that still has these materials and make copies. Barring that, your company study room probably has some materials too, depending on how cool your company is, how well your last couple academic officers have done their job, and whether or not they've been lost in all the barracks shuffling around.
-Have the cadet think about enrolling in one of the RS programs (speed reading ftw, study skills, etc.). For those cadets who didn't come into the Academy with a great foundation in time management, scheduling, study skills, etc., these classes can be a lifesaver if they get a chance to take them early. They only last a quarter but fill up fairly quickly.
-See how plebe duties have been running. If they're being run after ESP ends (I fought this battle for four years as did a number of my classmates. We had almost won it and then I graduated. No idea if they tried to keep sticking to avoiding this), and your plebe isn't doing homework until after, they're probably not getting close to the sleep they need. Not a ton you can do to actually change this, but you can talk with your SL and PSG if it seems to be impacting their performance. This also applies to whether or not y'all are doing open door ESP. Depending on if you are in divisions or hallways, I know that open door ESP was a bane of my existence. You can talk with your CoC if you think this isn't helping (i.e. everyone and their mother would stop by our room if the door was open because we were right next to the Q and created numerous distractions that interrupted my work from getting done) to either suggest closed door ESP where you or the SL does periodic checks for the plebe to ensure he/she is actually using the time to study or move his/her work to the library.
At the end of the day, you can't do the work for them. You can only help to create the environment and provide resources for them to use to succeed. There's a learning curve, which I'm sure you remember yourself, to time management at the Academy. People fail WPR's. As long as they don't make it a trend and you see progress and effort, don't necessarily jump all over the plebe. More stress added to his/her day isn't going to help. Don't stop caring though. Its a sign you're taking your job as TL seriously which you should be proud of.
Feel free to pm me with anything else you have questions on or want to talk Army.
