Prep Alum Journalist Interviews Chief Executive Aileen Hefferren

Not a natural athlete, Aileen Hefferren didn’t let that stop her from joining a sports team. She chose cross country and competed in high school and college. “The only way to get on a team then was to do something that just required gutting it out,” she said. Hefferren would eventually be good enough to qualify for the Boston marathon, with a personal record near the 3 hour, 30 minute mark. “It’s just about grit and determination,” she said. “It’s much like Prep.”

Prep for Prep, in search of contingents XL and PREP 9 XXXI this year, has had two leaders in its history: founder Gary Simons and Hefferren, since 2002. The mission of the program, its heart – to identify and develop leaders of color through educational opportunities – has not changed during her tenure. But, she added, the execution of that mission has only become more complicated. “What’s different, in a word, is competition,” she said. “There’s more competition to find the best kids, to find the spots in independent schools, and then to find the dollars to make it all happen.”

She is up to the challenge. At a recent visit back to her alma mater, Kenyon College, for a Board of Trustees meeting, her former coach praised her determination, saying he had never seen a runner squeeze out more from the limited athletic ability than she had. “I took it as a compliment,” she recalled, laughing. Her racing days are over, but her drive is undiminished. “Here at Prep for Prep, competition, that’s what we do,” she said. “We strive; we are always looking to do better.”

Hefferren is only the second generation in her family to attend college, following her father who grew up on the blue-collared south side of Chicago. He was one of two students from his high school class to attend college. “It was really instilled in him that education was important,” she said. He would eventually get a PhD in chemistry and become a researcher. After getting married, he moved his family – which would grow to include Aileen, her two sisters, and brother – to the racially diverse suburb of Evanston. “I grew up and thought this is the way it’s supposed to be, you go to school with kids from all kinds of different backgrounds,” she recalled. But as she progressed in her high school career, she noticed that though racially diverse, her high school, like Evanston as a whole, was segregated.“Honors and AP classes were completely white,” she recalled. “That’s not the way it should be.”

After graduating summa cum laude from Kenyon in 1988, she met her future husband, Charles Harkless, six weeks out of school. She was looking for a place to stay temporarily in DC and a mutual friend suggested a high school friend of Charles. “I will say that for me it was love at first sight,” she remembered. Not so for Charles. “He thought I was someone else, someone he had gone to school with,” she said laughing. They began dating after about a year, she recalled, and when he moved to New York, Hefferren decided to follow. Looking for a job, she came across a help wanted ad in The New York Times in the spring of 1992 for an organization called Prep for Prep. “Everything that I thought was important was in one place,” she said. “Prep was making incredible opportunities available to really, really smart kids. But it wasn’t a hand out; you were going to have to work your tail off.” She interviewed with Simons for hours. “It was really incredible what he had built and how successful the students had been.”

At 25, she was named Prep’s Director of Operations. One of her first acts in her new role was to put on rubber gloves and clean out the fridge. “It was far from glamorous, it was early Prep, with a staff of 25 and a budget of a couple million dollars,” she said. “No project was too small for me, and I got to learn the whole organization.” She would eventually rise to become Director of Development, in charge of fundraising.

In 2002, after a brief period away from Prep exploring other options and, now married to Charles, having the first of two sons, she was asked by Prep’s Board of Trustees to return as Chief Executive. “The reason I have stayed so long is that seeing what students and alums have done with this opportunity is incredibly rewarding,” she said. She now starts most her days walking to work from her home in Harlem or Trinity School, which her sons attend. On her march she collects her thoughts before what are invariably hectic days. “What I’m churning through my mind is what the priorities are for the day, what am I trying to accomplish,” she said. “The day is usually a mixture of external and internal obligations. No two days are alike.”

As Prep has grown – now with a staff of 64 – so have the challenges it faces. Parents now have more schooling options with the rise of charter schools. And independent schools are far more diverse than in the early years of Prep. “When Prep started most of these schools were lily white,” she said. “Now the schools are far more diverse than they used to be, which is a great thing.” The budgetary demands have multiplied several times over. The program now requires $11.3 million annually, all raised from private sources. The financing powers a program that has greatly expanded from a few dozen elementary school children running the hallways of Trinity, dragging oversized backpacks. “Our leadership component used to be skeletal, it was one person doing summer internships. Now we have three people. We put on dozens of seminars, we have college guidance, undergraduate affairs,” she said, naming some of the dynamic innovations added on since she was hired. Recruiting and retaining qualified staff has also become more challenging, she said. “Everybody wants the people we hire,” Hefferren said. “Millennials will often have four jobs in their first ten years out of school.”

Prep has matured as an organization, however, she added. One sure sign is that about half of the 364 internships the program helped students connect with this past summer came through alums. And the new Prep Alumni Association Council is another positive indication, she added. “I am so thrilled by the establishment of the Council,” she said. “What’s so exciting is that the Council gives alums opportunities to connect with each other in direct and more frequent ways.” Prep has recently found itself in a transition with the retirement of several long-time senior staff. “I think you are always in transition,” she said. “If you are not, you are stagnant.” The mission remains, though she notes with great pride that there are 719 Prep kids currently in independent schools with more than 2,800 college graduates. “Our work will not be done for some time,” she said.

And it’s a mission that is as intensely personal as it is professional. With her marriage to Charles, who is African American, her two boys, now 12 years old and 15 years old, are sure to face some of the same challenges as Prep students, more so in the current political climate. “I think this program is essential now,” she said. “It was always incredibly important, but now it’s more important than ever.”

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Ezequiel Minaya (V/Trinity '89, Guilford '95) MA, Berkeley '01 is a member of the Alumni Association Council and is currently a reporter for the Wall Street Journal. Ezequiel has covered the world, having most notably spent 13 months in Iraq as an embedded war correspondent writing for Stars and Stripes and five years covering Venezuela for the WSJ. He has also written for the Dow Jones, Village Voice, Los Angeles Times, McClatchy newspapers, The Press-Enterprise, the Houston Chronicle and the Southern Poverty Law Center.