TO THE LETTER Students converse with iMentor volunteers via email.

Photo: Jodie Love

In the late 1990s, hedge-fund manager John Griffin struggled to establish a rapport with the high-school student he was mentoring. Once he established an online correspondence with the teen, though, their relationship blossomed—and so did the idea for iMentor, a volunteer program Griffin cofounded that connects busy professionals with NYC students for one-on-one e-mail–based relationships. Almost a decade later, the group has a staff of eight full-time employees helping nearly 700 students improve their academic and professional skills. “A lot of people want to mentor but don’t because they assume it’s too much work,” says iMentor executive director Mike O’Brien. Using the Web, he explains, “makes it easy to cross that divide.”

To get the ball rolling, iMentor assigns weekly e-mail prompts for the volunteers and students to work on—topics might include the student’s family history, personal heroes or career goals. The exchange keeps communication flowing in a structured manner, while the ease of e-mail reduces the anxiety teenagers can feel from encounters with grown-ups. But can an e-mail really help set someone on the right track? “We had a student who worked with one of our mentors from freshman year all the way to graduation,” recalls O’Brien, “but he didn’t know what to wear to a job interview. So he e-mailed his mentor for advice, who then forwarded it to 20 of his contacts. Within a day, a kid who had never been on an interview was getting advice from dozens of professionals regarding all aspects of the interview process. He pieced together his first suit, got the job and now works at Bloomberg.”

Chanique, an outgoing student from Bed-Stuy, says she’s really connected with her mentor. “She’s 23, so she understands when I have problems with schoolwork or when I fight with my sister.” Only 15 herself, Chanique also interns at iMentor’s Wall Street offices, helping to screen potential volunteers. Her ability to recruit at such a young age hints at the impact iMentor has had in her development. “I definitely know what we’re looking for—someone who’s kind, smart and there when we need them.”

While the core of the iMentor relationship is regular e-mail contact, the group encourages face time between volunteers and mentees and sponsors frequent group outings, which might consist of a Mets game, a college tour or a visit to MoMA. “Mentees are able to experience some of the city’s cultural offerings, while volunteers get to meet other mentors and have their eyes opened about underserved neighborhoods,” says coordinator Ellen Mahoney. “Advocating change in the student’s life often transfers over into changes in the mentor’s life.”

To volunteer with iMentor, contact Ellen Mahoney at 212-461-4330, e-mail ellen@imentor.org or visit imentor.org.