Help in Creating a Teen Mentor Program

[AENeuman]

I am creating a mentor/shadowing program next year for high school jr. and seniors. I do not want to just do the typical follow around someone who works in field you might be interested in thing. Rather, the main things I want my students to get out of this are:
Reference/recommendation, either academic or professional
Knowledge of an adult, career oriented work place
A relationship with an adult that is interested in their career path that is not a parent or teacher
Professional socialization (expectations, language, attitude, etc)

The main reason for wanting to do this is that i feel most of the students I deal with (diverse, "new" middle class, silicon valley) will not learn how to be or act like an adult until they are 24. Meanwhile those who do figure it out are destine to be their bosses.

Questions:
What skills, information do you wish you had a professional adult give you when you were 16-18?
If you were given one of my kids what would you have them do? I feel most job shadowing gets boring after 15mins.
(Most importantly) What could the students do for you that would demonstrate skills that would be good for your field and good for their resume? How much time would you need to see them?

Thank you very much.