Help me help this kid pass his important test.

We have recently become close to a 20 year old young man.  He is working on his certification in his field.  He has passed all but one of the tests.  He is an extremely smart guy and I have a feeling he never had to study to get good grades in school.  His "little" heart was just defeated when he got in the car having failed that one test by three points.  He is so close!  IF he were MY CHILD, I would give him some pointers and in a way, put my foot down and say YOU ARE GOING TO STUDY--------HOURS EVERY MORNING, night, whatever. He studies pretty hard but waits until just a few days before the test to really get motivated. I've offered to go over the sections where he is struggling and write little clues for each area.  I mean, the binder he has to study is at least four inches thick.  Nobody could memorize all of the information in there so we need to go pick out the main points, memorize them and have a strategy for the details. I'm a (first grade)  teacher and am not saying that I know anything about what he is learning BUT the teacher in me can consolidate  it into reasonable pieces.  I've offered to do that and he said yes . I don't want to be pushy (from what I hear his own mom is pretty good at that)   Tonight he is depressed and feeling down on himself when tomorrow I want to say HEY go sign up for your test and get in ASAP and study a few hours every day until then.  Ugh!  I love this kid and want him to be successful.

Should I be pushy and treat him like my own kid?  Should I invite him over so I can give him some pointers on how to study and how to break the material into manageable pieces?  Should I write him an encouraging note asking what would help him or just telling him that i believe in him???  Time's a wastin' and he is at a loss at what to do.