Mike O'Brien
Ashoka Fellow since 2012   |   United States

Mike O'Brien

Recognizing the inherent capacity constraints faced by teachers and guidance counselors, Mike O’Brien is working to unlock what he calls "human capital solutions," by enlisting the vast…
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This description of Mike O'Brien's work was prepared when Mike O'Brien was elected to the Ashoka Fellowship in 2012.


Recognizing the inherent capacity constraints faced by teachers and guidance counselors, Mike O’Brien is working to unlock what he calls "human capital solutions," by enlisting the vast array of experienced and caring adults within a community to play a targeted and impactful role in student's development.

The New Idea

Mike is out to improve college readiness via high quality, technology-enabled mentoring. Believing that it is no longer enough to merely prepare students to graduate from high school, Mike is helping educators shift their focus to equipping students for college and success in the workplace: environments which demand a range of social and emotional skills not currently addressed by traditional K-12 education.

Mike recognized that the popular practice of mentoring was uniquely capable of meeting such needs, and so he set out to do three things. First, he sought to replace the high level of variability and ineffectiveness associated with mentoring with a reliable and outcome-driven model, developing a flexible program model that pairs every student within a school with a personal mentor, and a multi-year, outcome-driven curriculum. 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. Mentors are thus able to offer support on their own time without compromising quality, removing one of the most significant barriers to volunteer recruitment. Second, he pioneered an integrative whole-school approach: rather than work with a few students at a time, Mike partners with schools to ensure that every student has a mentor, with the result that all aspects of student support can work in concert with one another.

Mike established iMentor Interactive to improve the quality of mentorship programs as a whole, enabling schools and college access organizations to create or improve an existing mentoring program. iMentor Interactive serves as an online partnership portal, offering a combination of curricula and best practices, research and evaluation tools, and tailored consulting and support.

The Problem

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 dropout 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 percent complete college. For students in the uppermost income quartile, that number is 84 percent.

This is largely attributable to school design, and 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 today’s teachers and principals are held to account only on the basis of the first component, and 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 percent of his/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 and/or afterschool programs and so-called “retail supports” for critical college preparation. For students in low-income schools, who are often the first in their families to go to college, the result is a woeful lack of preparation.

That 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 take years to develop and are best established 1:1. 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 U.S. are enrolled in some form of mentorship program.

The quality and reach over 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 Strategy

The program begins with a one-month orientation. 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 U.S. 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 lasting persistence. iMentor assigns each pair a Program Coordinator to provide mentors with coaching and training in best practices and to monitor progress toward 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 through which both parties can admit 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 or maintain a quality mentoring program. 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 can play in that preparation. Partner organizations can choose to follow the model with a high level of fidelity, or to replicate the principles, tailoring the model to their existing programs and needs through an extended program design process conducted in partnership with the iMentor staff.

Mike has reached a powerful inflection point, moving beyond just changing the standards of practice among mentoring organizations, to fully reimaging the role of guidance counselors. 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 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 users, in order to leverage their advocacy potential in much the same way that Teach for America has done with theirs.

Current partners include leading school networks and college readiness organizations, including KIPP, Through College, Single Stop USA, Gates Millennium Scholars, Bridgeport Public Schools, College Possible, City Year, and the Hispanic Scholarship Fund, totaling more than thirty leading school networks, programs, and districts across the country. To date, iMentor has matched 10,000 students to trained mentors through 1:1 pairings. iMentor currently serves 2,600 students in NYC, and an additional 1,900 through iMentor Interactive. 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. Mike plans to continue to grow the number of partners served, and to expand the New York model into 2 to 3 additional districts, in order to establish the whole-school approach as a viable national model, while turning his attention to a broader range of policy shifts.

The Person

Mike has experienced the importance of mentoring firsthand, as both mentor and mentee. Having lost his father at the age of 15, he credits a network of caring adults from within the community—and in particular one person—with giving him the support he needed to succeed and showing him the way.

Immediately after college, Mike became a teacher at a school in Brooklyn that was among the 5 percent worst-performing in NYC, with a graduation rate of just 30 percent. 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. Of the five students from his first class accepted into college outside of NYC, not one made it through his/her first year. 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 Mike joined iMentor, which had just started up as a rudimentary organization aimed at matching the talent and resources available within NYC to the students living in isolated low-income communities nearby. Having arrived at the same insight about what was needed, Mike set out to create strategies and the right team that could guide the idea at its fullest system change expression, stepping into the CEO role formally in 2007 and growing the team from 15 to 100.

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