Discusses considerations and steps involved in establishing a coaching program to help prepare high school students for college. Mentors who have established trust and connection with teenagers can provide a role model for positive behaviors, such as studying hard and staying away from trouble, and can encourage students to take the right college-preparatory classes, offer tutoring and academic assistance, and help them get information about different college programs and the availability of financial aid. Employers, community-based organizations, and interested volunteers get practical guidance on starting and operating these kinds of mentoring programs, including: (1) activities associated with the first stages of program development, such as assessing needs and potential resources and developing the program’s goals and objectives; (2) procedures for recruiting, screening, selecting, and training mentors and for recruiting and orienting program participants; and (3) steps involved in matching mentors with young people, keeping track of the mentor relationships, working with parents, dealing with obstacles to success, and evaluating and making improvements to the program. Also contains profiles of successful mentoring programs, a checklist for mentoring program development and operation, and lists of relevant programs and mentoring organizations.