United States,

As CEO of iMentor, Mike O’Brien is working to increase the capacity of public high schools in the United States to provide students with personal support that prepares them for college. iMentor’s programs provide an innovative human capital solution for schools by enlisting the vast array of experienced and caring adults within a community to serve as mentors who help students develop critical skills linked to college success.

This profile below was prepared when Mike O'Brien was elected to the Ashoka Fellowship in 2012.


As CEO of iMentor, Mike O’Brien is working to increase the capacity of public high schools in the United States to provide students with personal support that prepares them for college. iMentor’s programs provide an innovative human capital solution for schools by enlisting the vast array of experienced and caring adults within a community to serve as mentors who help students develop critical skills linked to college success.


Mike has led the development of iMentor’s programs to leverage the unique benefits of high-quality mentoring to ensure more students attending schools in low-income communities are prepared for and succeed in college. Realizing that young people need more than a high school diploma for long-term success, iMentor helps educators prepare students for college and the workplace—environments that demand a range of social and emotional skills not currently addressed by traditional K-12 education.

Mike advocates that mentoring is uniquely capable of providing students with the individual guidance they need to develop these social and emotional skills. Under his leadership, iMentor has developed several key innovations that make mentoring an effective college success resource for young people. First, recognizing that students who would normally opt into a mentorship program are not necessarily the ones who need it most, iMentor developed an integrative whole-school approach. Rather than work with a few students at a time, iMentor partners directly with public high schools to ensure that every student has a mentor, embedding mentorship and a college going culture deep within the school.

Additionally, iMentor addresses the high variability of outcomes often associated with mentoring by pioneering a more reliable and results-driven model. iMentor’s programs follow a rigorous, multi-year curriculum that guides mentor-mentee interaction to ensure pairs develop a strong bond while students build key college-readiness skills. Over the course of three to four years, beginning in high school and extending through students' college transition period, mentors and mentees exchange weekly emails and participate in monthly events, covering everything from self-advocacy to navigating financial aid applications. This model allows mentors to offer support on their own time without compromising quality, removing the most significant barriers to volunteer recruitment and effectiveness.

Finally, Mike spearheaded the launch of the iMentor Interactive program, a national partnership program, that brings iMentor’s effective mentoring model to communities across the country. iMentor Interactive provides consulting services, curricula, and technology tools to nonprofits and schools so they can implement their own effective mentoring programs in the iMentor model. Current partners include 18 leading organizations and schools, including Miami Dade College, College Possible, City Year, and the Hispanic Scholarship Fund.

To date, iMentor has matched 10,000 students to trained, college-educated mentors through one-to-one pairings. iMentor currently serves 2,600 students through its direct-service program in New York City, and an additional 1,900 through iMentor Interactive. Mike plans to continue to grow the number of partners served, and to expand its direct-service model into three additional cities, in order to establish the whole school approach as a viable national model, while turning his attention to a broader range of policy shifts.


While the link between educational attainment and economic prosperity is no longer in doubt, access to a college degree remains elusive for a large percentage of today’s students. Each year, one-third of public high school students fail to graduate: statistics that are far worse for students of color and students living below the poverty line. Fully one-half of Black and Latino students drop out of high school. For those who do graduate, only one in three enrolls in college and one in seven earns a degree. The comparative statistics are dismal: of students living in the bottom income quartile, only 8.3% complete college. For students in the uppermost income quartile, that number is 84%.

This is largely attributable the mismatch between the knowledge and skills required to graduate high school, and those required to enter and succeed in college and beyond. Extensive research reveals that there are three things that are essential for college success: academic preparation, non-cognitive skills—those not measured on standardized tests, including empathy, collaboration skills, and communication abilities—and an understanding of how the college process works, from admittance to graduation. Yet schools traditionally are held to account only on the basis of the first component—measured through students’ mastery of key academic subjects—leaving schools poorly equipped to meet students’ non-cognitive needs and to provide the individualized support needed to effectively navigate the college system.

Guidance counselors—the individuals traditionally expected to play that role—are wildly under-resourced. The average high school student-to-counselor ratio is 459:1, while the average counselor spends roughly 35% of his or her time working individually with students: a percentage that, if divided equally, would amount to less than one hour per year per student. The reality is made worse, however, by the fact that most counselors spend the vast majority of their time with a small number of students experiencing significant personal and psychological challenges. Without individualized, proactive support, most students rely on their parents, after-school programs, and/or other individually acquired supports for critical college preparation. For students attending schools in low-income communities, who are often the first in their families to go to college, the result is a woeful lack of preparation.

True college preparation requires that students take into account a range of personal, academic, and career considerations. Adults wishing to provide meaningful support thus require a close, candid relationship with the student—relationships that take years to develop and are best established on a one-to-one basis. Even under the best of circumstances, therefore, schools are unable to provide the staff support necessary to meet such needs.The idea of youth mentorship—matching students to a caring adult role model, with whom they can build key relationship skills—has therefore become a popular tool to fill the gap that guidance counselors and educators cannot.

Today, more than three million students throughout the US are enrolled in some form of mentorship program. The quality and reach of such programs, however, are severely compromised for two reasons. First, most mentorship programs demand weekly in-person meetings between mentor and mentee, and lack the flexibility most working professionals looking to give back would need. Low-income schools—particularly those in urban areas—are thus unable to effectively tap the resources available within the community, even when demand for mentorship opportunities exists among both students and adults. Secondly, the quality of mentorship is highly variable, due to a lack of standards for the field. Schools and programs evaluate their success according to the number of students they are able to match to mentors, rather than the outcomes that come of that relationship. Those who are not instinctively good at mentorship have little by way of established curricula, best practices, or evaluation tools to see where they could improve.


The program begins by making a strong mentor-mentee match. Unlike most mentorship organizations, which match students and adults based on expressed similarities, iMentor has found that the key determinant of success in a mentor relationship lies in giving students a say in choosing their mentor. Students thus begin by naming what they are looking for, requesting, for instance, someone who had a parent pass away, or who immigrated to the US as a child. A carefully calibrated algorithm then makes suggested matches within the mentor network, much as a dating site does.

Students participate in one of two tracks: College Ready, which pairs students with a mentor beginning in the ninth grade through their senior year of high school, and College Success, which begins in the 11th grade, and lasts for three years, seeing students through graduation, enrollment, and their first year of college in order to ensure persistence successful transition. iMentor assigns each pair a case manager to provide mentors with coaching and training in best practices and to monitor progress towards achieving program benchmarks.

The program is designed to be flexible for both students and adults. Mentors and mentees exchange weekly emails around a carefully selected writing prompt and come together for monthly activities, each geared toward a particular outcome. Over the course of the relationship, students learn to improve their communication and critical thinking skills, develop problem solving skills and resiliency, and grow their leadership and personal passions, as well as develop the financial literacy skills and study habits required to persist through college. In addition to helping pairs work toward an explicit set of goals and competencies, the activities are designed to establish a level of comfort and candor between pairs so that both parties feel comfortable discussing their failures and challenges.

Drawing on the research and development done through iMentor NYC, Mike launched iMentor Interactive (iMi) in 2009, to support any school or organization looking to start a quality mentoring program in the iMentor model. Partners can take full advantage of iMentor’s web-based technology platform, curricula and training materials, and intensive consulting support. Organizations can use the site to match students to volunteers, host email communications, and identify and share best practices. Users can also take advantage of surveys and evaluation tools to keep track of both the number of active pairs and the impact of the relationships, aiding in their own fundraising and recruitment efforts. The data then helps to inform the case for the mentorship movement as a whole, enabling iMentor to advocate for new standards and policies to better equip students for college, and to articulate the unique role that supportive adults outside the formal education system can play in that preparation. Partner organizations follow the iMentor model with a high level of fidelity.

Mike has led iMentor to reach a powerful inflection point, moving beyond just changing the standards of practice among mentoring organizations, to fully how our nation’s high schools approach college readiness for their students. Rather than allocate funding according to inputs—such as the number of mentors provided within a school—federal grants should instead focus on outcomes, he says. His ultimate vision is that in ten years time, rather than employ one or two guidance counselors who serve several hundred students at once, schools will instead hire a full-time staff person whose job is to coordinate personalized mentoring relationships between every student and members of the community. He is thus beginning to turn his attention to policy standards, and to the innovations required to change the underlying structures in K-12 education. To that end, he is exploring a variety of mechanisms to activate his alumni base of more than 20,000 mentors and mentees, in order to leverage their advocacy potential in much the same way that Teach for America has done with theirs.

iMentor currently serves 1,900 students through partnerships with18 organizations that include College Possible, City Year, Miami Dade College, and the Hispanic Scholarship Fund. Both iMentor NYC and iMi operate on a fee-for-service basis, according to the size of the school or organization served and the number of students actively involved.


Immediately after college, Mike became a teacher at a school in Brooklyn that was among the 10% lowest-performing in NYC, with a graduation rate of just 30%. He soon discovered that no matter how effective he was as a teacher, nor how intelligent or ambitious his students were, academic preparation alone was not enough to carry students through college and onto a path out of poverty. Remembering a semester he had spent in college living in a township in South Africa, surrounded by extreme poverty and segregation, he became deeply aware of the artificial isolation that surrounds low-income communities, and what would be required to break it. In 2003, he joined iMentor, which at the time comprised a staff of 5 people, to find a way to match the extraordinary talent and resources available within NYC to the students living in isolated low-income communities nearby. Over the next four years, he played a variety of roles, serving as Director of Programs and Director of Development, before conceiving and launching iMentor Interactive. Upon taking over as CEO in 2007, he grew what was then a staff of 15 to what are now nearly 90 employees, and a one-million dollar budget into an $11 million organization.