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On Writing The College Application Essay Secrets Of A Former Ivy League Admissions Officer

In his new book, “The Battle for Room 314,” Ed Boland chronicles his year as a teacher in a low-income New York City school. It was the polar opposite of his previous experience — assistant director of admissions for Yale University. As the class of 2016 eagerly awaits letters from colleges, Boland reveals what really goes on behind the scenes in this excerpt.

Working as a gatekeeper at Yale gave me lasting insight into the formation of the American elite.

My colleagues and I were sent to scour the country looking for the best and the brightest young minds. In the fall, I went everywhere, from Charleston, W.Va., to Kokomo, Ind., to Montreal, to the Upper East Side of Manhattan.

I was welcomed with varying degrees of energy and enthusiasm. In Ohio, an eager headmaster at a boarding school took me to a nice lunch and toured me around the campus in his convertible with the top down. At a large public school outside Detroit, I sat outside the cafeteria at a sticky table chatting with a representative from a local cosmetology school. Largely ignored by the students, we passed the time talking about the challenges of having very fine hair.

Brilliance and stunts

After the recruitment season wrapped up, the admissions staff returned in the late fall to New Haven and started the early-decision process. We would spend hour after hour poring over huge stacks of applications and green-bar computer reports.

We parsed transcripts and called guidance counselors with questions like: “So far, there seem to be three students ranked number one in your school who have applied to Yale. How do you account for that?” As a first step, two staff members read each application and assigned it an overall ranking of 1 (TAKE THIS KID!) to 4 (NO WAY!).

The applicants were an impressive lot. A girl wrote a brilliant feminist essay — worthy of Harper’s, really — about gender and socialization, revealing that she was a phantom serial farter in public and yet no one ever suspected because of her gender.

An aspiring art major sent in a dazzling, poster-size pen-and-ink drawing of himself suspended high over the campus on a pair of gymnastic rings, his body forming a perfect Y for Yale. A Vietnamese refugee wrote about finding solace in a school in Nebraska after a near-death experience as a “boat person” when she was
6 years old. They all waltzed into the freshman class.

Being too clever could backfire.

A self-saboteur from Chicago wrote her essay about her fear of going to the dentist — in backward letters, colored pen, and a spiral “Yellow Brick Road” pattern; not the kind of thing you want to tackle in a mirror at midnight.

‘An over­eager Eagle Scout on the wait list pitched a tent on the lawn of the Admissions Office to show how ardently he was interested. I am sure he enjoyed Haverford.’

 - Ed Boland

A few years before, an over­eager Eagle Scout from Pennsylvania on the wait list had pitched a tent on the lawn of the Admissions Office to show how ardently he was interested. I am sure he enjoyed Haverford.

Having the president of Stanford write you a letter of recommendation to Yale might seem like a good idea, but it resulted in a note from the dean that said, “If he’s so enamored of the kid, let Stanford use a spot on him.”

It was the kiss of death when the daughter of a prominent alum from Columbus, Ohio, “discovered” she was one-sixteenth American Indian and checked the box for Native American.

And then there were the athletes. After fierce pressure from the athletic department, I had to admit a highly sought-after French Canadian hockey recruit. He had crappy grades, dismal scores, and his essay consisted of one sentence scribbled hastily in pencil: “I want to bée a great hockey player.” To add insult to injury, he decided to go to Boston University.

‘Reject the state!’

After the preliminary votes were cast, the Admissions Committee was convened. Composed of faculty members, deans, and the most senior admissions representatives, they served as judge, jury and executioner for the nearly 14,000 applicants.

Because competition was fierce and time short, you had to make your notes about the kids you were advocating for pithy and ­almost Zagat-guide-esque:

“Another hothouse flower with a perfect GPA, pass!”

“Virtuoso bassoonist and published poet at 17, an Eli to the core.”

“Milquetoast, yes, but brilliant milquetoast.”

“AP English teacher (Yale Class of ’79) says she is the most original thinker she ever taught, not just a ‘rara avis’ but ‘rarisima avis.’ ”

Any member of the committee could challenge you to back up your recommendation on any candidate in your region. After you made your case and answered their questions, the committee of eight or so would decide a candidate’s fate on a wacky voting machine, rumored to have been specially designed by some nerdy electrical-engineering major. It had small electric consoles from which members would anonymously flip a switch to light up either a thumbs-up green light, thumbs-down red light, or wait list white light. Any applicant with more than a total of two reject and/or wait-list votes was automatically denied.

Because we had to get through about 300 applications in each two-hour committee session, we developed shortcuts.

You could look down at the names of four or five kids from one school who were terribly smart but not exceptional and say, “Reject the entire high school”; sometimes you could go further and say, “Reject the page,” and send 20 kids on a single page of computer paper packing; or, most famously, “Reject the state,” when it came to sparsely populated places like North Dakota or Wyoming.

Deciding which 14 percent of the applicants would get the golden ticket was really tough work. Once the children of alumni, recruited athletes, underrepresented minorities or regions and students interested in underenrolled majors were considered, there wasn’t much room for your generic genius. (By today’s standards, 14 percent doesn’t seem so brutal. In 2014, Yale got nearly 31,000 applicants and accepted a mere 6.3 percent of them.)

Fingerprints of privilege

The great majority of students we admitted were truly brilliant and had busted their tails to get there. But the fingerprints of privilege were still present. You had to look a little harder to see them and resolve not to let them unfairly influence you.

It was immediately obvious that kids from elite feeder schools had been coached for years on their interviews, essays, and every conceivable form of standardized testing. Many of their college counselors had worked in elite admissions offices; their tutors had Ph.D.s. They knew prominent alums who would write recommendations on thick, creamy bond paper.

The letters arrived daily from white-shoe law firms, governors’ mansions, and — in yet another shock to my blue-collar brain — vacation homes with proper names on engraved stationery: “The Manse, Little Compton, Rhode Island” or “Coral House, Hamilton, Bermuda.”

As I tried to sort out fair from foul, Suzie, a perennial champion of the underdog, gave me advice I will never forget: “It’s very easy to throw the prize at the kids who finish the race first, but always look at the incline they faced. That will tell you much more.”

Once the more clear-cut cases had been decided, things got fuzzy, political, and sometimes unfair. It wasn’t news to me that the process wasn’t entirely meritocratic. It wasn’t news to me that people were willing to use any and every angle to game the process.

But it was a revelation about ­exactly what forms those advantages would take and how they were displayed: sometimes furtively, sometimes brazenly.

Old and new

One trip took me to an overstuffed wing chair in the august lounge of the Yale Club of New York. The school’s motto, “Lux et Veritas,” was stitched into the carpet, embossed on my coaster, and emblazoned on the jacket of the old waiter who had grudgingly brought me iced tea.

I was waiting for Hal Buckley and Francis Alcock, the two Old Blues who headed the local volunteer alumni group that conducted the alumni interviews ­required of all applicants. I had been forewarned by the dean of admissions that the New York group was chafing at the recent difficulty many of the Manhattan prep schools had had in getting students accepted to Yale, many of them children of alumni. Most of the schools had been feeders to Yale for nearly a century; one even predated the university’s founding in 1701 by 70 years.

I had talked to them by phone but had never met them in person.

Retired Wall Streeters, they were both old, smart, white and pedigreed. With matching sets of wiry gray eyebrows, they could have been twins. We exchanged some initial pleasantries, and then I braced myself for the onslaught.

“We used to hold our receptions for admitted students here, but your Admissions Office says it’s too stuffy and we’d scare off kids who aren’t from typical Yale backgrounds. Have you ever heard such twaddle in your life?” said Hal, the crankier of the two.

I scanned the room — a gorgeous mausoleum, majestic but imposing as hell, filled with mean-looking old men who appeared ready to lower their Wall Street Journals and scream, “Get off my lawn!” in raspy unison.

“Why, it’s such a striking space. Who wouldn’t like it here?” I was trying to get on their good side.

“I just hope we have a better rec­ord in getting some kids in, because last year was, quite frankly, a debacle. A travesty, really,” said Hal.

“I assure you I’ll do my best to advocate for New York,” I said with conviction, at the same time trying to suppress the images in my head of Statler and Waldorf, the pair of grumpy-old-men Muppets in the balcony.

Francis, who was somewhat friendlier, added, “We have a great crop of kids from Manhattan this year. Let’s see. We’ve already discussed that Westinghouse Science Competition finalist from Stuyvesant, the Latvian fencer from the Trinity School, and the daughter of the dean at Columbia Law School whose father is a close friend of the president of the university.”

‘Once the children of alumni, recruited athletes, underrepresented minorities or regions and students interested in underenrolled majors were considered, there wasn’t much room for your generic genius.’

 - Ed Boland

“Yes, I saw your write-ups on all of them in the office. Very thorough. Thank you.”

Francis leaned in and peered at me over the tops of his tortoiseshell glasses. “Over the weekend, we interviewed an extraordinary young woman from Miss Bartlett’s School. She has real Yale polish. Great intellectual curiosity.”

I checked the rumblings of a groan in my throat.

He continued. “But she lives in the South Bronx. From a very poor Puerto Rican family. Raised by a single, unemployed mother with three other children. She would be the first in her family to college.

“Her name is” — here he slowed down as if he were ordering a difficult-to-pronounce dish in a foreign restaurant — “E-mman-u-el-a Gut-i-err-ez.” It was sweet how respectful of her name he was trying to be.

“Really?” I perked up. I knew from my experience at Fordham how rare a profile like hers was.

I realized that I had judged these guys wrong. They weren’t just trying to safeguard spots for the kids of their alumni buddies.

They ran through some more names, handed over a new stack of interview reports, and slapped me on the back as I got in the elevator.

Francis smiled. “Good luck in committee, Ed. Keep your shirts starched and your powder dry.”

“And get our kids in,” I heard from Hal as the door clanked shut.

A hard miss

I returned to New Haven a few days later and pulled Emmanuela’s application out of a teetering pile. Her grades were strong and her Latin teacher had written a glowing recommendation, but she wasn’t at the very top of her class. She was a first-rate debater, though, and had founded the school’s Afro-Latina Alliance.

When I presented her in committee, there was a long debate about her merits and careful consideration of the dozen or so other applicants from her school, each of whom could likely excel at Yale.

In the end, Emmanuela was muscled out of the running by some superstars in her class and put on the wait list. The alums were furious. I got a testy voice mail from Hal the day after the decision letters went out. “For Pete’s sake, your office is sending us mixed messages. You tell us to find gems like Emmanuela with atypical backgrounds, but then you don’t accept them. What gives?”

Years later, I learned that Emmanuela graduated from Columbia, where she did impressive work organizing Harlem tenants against a local slumlord.

After graduation, she wanted to improve the lot of low-wage earners like her mother, and she became a widely respected union organizer and leader for health-care workers. In 2013, she ran for lieutenant governor of New Jersey on the Democratic ticket. We had missed a true gem.

Excerpted from “The Battle for Room 314: My Year of Hope and Despair in a New York City High School” by Ed Boland, out this week from Grand Central Publishing.

During my time in the undergraduate admissions office at Cornell — and even more so as a college application adviser — I've come across stellar academic students whose applications didn't get the type of results they felt their hard work merited.

I often tell the story of an applicant to the atmospheric sciences program at Cornell whose application I remember reading.

This particular student wrote his essay about his passion for understanding weather patterns. That is certainly a trait expected in an earth and atmospheric sciences student, but this student's fit with the program really came to life as he described the weather station he had built at home.

He had been collecting data and providing information to a cable news station, who then used his data in their weather forecasts. In addition to his own account, I read a teacher's letter of recommendation which corroborated his passion for weather sciences, as well as his weather station story.

After reading, I thought, this student clearly will get my recommendation for admission, because he has the grades, the test scores, and a demonstrated intellectual interest in his chosen program. Trifecta! He had hit the nail on the head in expressing "fit and match."

I contrast that story with the dozens of high-achieving students whose applications I've read or whom I have advised over the years. They were academically stellar and had adequate standardized test scores, but their applications lacked tangible indicators of their passions: a project, experiment, portfolio, or an endeavor on which they spent substantial time learning, tinkering, or creating.

A few years ago, I advised a student who had near-perfect scores on the SAT, a senior year loaded with the most challenging courses his high school offered, and a GPA that placed him among the top 5% at his high school. As a counselor, I felt this student would be highly competitive to his chosen colleges, and he did receive admission to some great institutions. However, to his disappointment, he was only offered a spot on the waitlist at his top-choice universities.

I later asked a former colleague who worked as an admissions officer at one of the universities at which he had been waitlisted about what might have kept this student from being admitted. After a brief review of the student's file, my colleague explained that the student's grades and test scores clearly indicated he was capable of succeeding at that school and that he was no doubt an excellent student, but that his application lacked tangible evidence of his passion for design and computer science.

She went on to explain that though he fared well in the applicant pool in terms of his numbers (GPA, class rank, and standardized test scores), most of the students who received admission to the computer sciences program had some sort of passion project which demonstrated their skill and interest in the field.

That conversation has stayed with me, and I've made a point to encourage all students to turn their dreams into assets by working on passion projects. I have seen high school students apply themselves this way before, like the team of students who created a device which uses localized vibration therapy to help autistic children attend mainstream schools.

I know another group of students turning their school's used cooking oils into bio fuel to help their school reduce its carbon footprint and operating expenses. I'm really impressed by these students, because not only do their projects give them a "hook" in the college application process, the projects give them purpose, technical skills, and the understanding that even as high school students they can impact the world in a positive way. I continue to encourage students to combine their knowledge with passion and apply it toward making an impact.

Scholarships such as 99Dreams (of which I am a sponsor) are great resources for students looking for a little funding and guidance in jump-starting their ideas.

Nelson Ureña received his B.S. in communication from Cornell University. He worked as an admissions officer in the undergraduate admissions office at Cornell and is cofounder and COO of Mentorverse, an online platform connecting college applicants to mentors who can guide them in the college admissions process.

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