The Student Advocate is a licensed social worker who works with the 36 students, their parents, and their teachers to maximize the effect of Rocking the Boat's youth development activities. She meets with participants in both group settings and private sessions throughout the semester.

Addressing students' academic, social, and emotional needs is of primary concern to the Student Advocate. Academically, she receives permission from parents for schools to release students' report cards, important in establishing a baseline for students' records of performance at school and in identifying patterns. In turn, the Student Advocate can provide a wealth of information to teachers, guidance counselors, and principals regarding students' learning styles, possible difficulties in the home, and perhaps untapped academic potential based on her observations of the student in action at Rocking the Boat. Socially and emotionally, the Student Advocate meets with each student at least two times each semester to gauge their experience. If issues are identified, the Student Advocate either addresses them directly or refers the student to a network of social services.

The Life Skills Program, organized by the Student Advocate, allows students to gain expertise and receive advice from professionals outside of Rocking the Boat in areas that are necessary to independent living but which students may not learn about at school or at home. In the past, Life Skills workshops have featured a nutritionist speaking about healthy eating habits; attorneys from the Bronx Defenders guiding a lively discussion on your rights if you are stopped by the police; and representatives from the local bank who had the students entirely captivated in a discussion about money management. The Life Skills program recently expanded to include field trips with small groups of students to locations that specifically target their vocational interests.

The Job Skills Advocate works with 16 Apprentices and up to 10 Program Assistants to facilitate their transition into the next phase of their lives. This position primarily concentrates on future opportunities, working one-on-one with Job Skills apprentices and Program Assistants (and any interested students) on range of job and college readiness skills, training them to become successful employees and helping to place them in future academic and work environments.

The Job Skills Advocate brings Apprentices to visit job sites, trade schools, and colleges; teaches them to present themselves professionally, helps them develop resumes, and guides them into their next steps in life.