This guide, which is intended for teachers interested in starting a workplace mentoring program, presents information about mentors and mentoring that can be used to match students with the right mentors in the workplace and help prepare and support students and mentors in enhancing the student-mentor match. The guide begins with background information about the school-to-work initiative and New York's Learning Standards for Career Development and Occupational Studies. The first section is devoted to the benefits of mentoring and mentoring program outcomes and partners. The next two sections explain the processes of selecting, preparing, facilitating, and evaluating students and mentors. Next, considerations in matching students and mentors are examined, and the mentoring relationship is described. In the next section 10 basic steps are outlined to establish and administer a workplace mentoring program. Also, building steps to help the mentoring program are described. The following helpful information is provided: 36 references and resources; addresses of 25 organizations and programs; and pertinent provisions of federal and state labor laws and addresses of 20 contacts. The final section, which constitutes approximately 50% of the guide, contains sample materials related to the following topics: planning the mentoring experience; understanding the qualities of effective mentors; being an effective mentor; and evaluating the learning experience. (MN)