In recent years, a number of structural changes have drastically altered the role of the Yale College dean. But 10 months in, Jonathan Holloway has brought something of his own to the position as well.

January was not kind to Yale College Dean Jonathan Holloway.

Over the span of less than 15 days, campus was racked with tragedy: the loss of a student’s life, two publicized allegations of sexual assault and a slew of robberies in Trumbull College. An attempt to catch the thief, in which a student was briefly detained at gunpoint, brought national attention to Yale’s policing practices. And it all happened surrounding only the second snowstorm to shut down Yale’s classes in 37 years.

Holloway had entered the second term of his deanship with new ideas. Before those “weeks of crisis,” he had been planning for new projects that would feature students’ voices on campus. But one chaotic day, he turned to Yale College Director of Strategic Communications Paul McKinley and told him they would have to put those plans on hold. He needed to spend the time “putting out fires.”

“For me that was a lesson, of a type. I find it hard to believe that we would replicate that kind of intensity during my term as dean,” Holloway said, knocking on the wooden arms of his chair.

As the former master of Calhoun College, Holloway had weathered his fair share of storms. After a few especially harrowing incidents woke him late at night, he never slept quite as soundly for as long as he was master.

But experiencing tragedy on campus is different in his new role. The highs are extremely high, he said, but the lows are “crushingly low.”

“You occupy the space in a different way — there are different expectations placed upon the dean of Yale College,” he said. “The great beauty of being a master is you know the constituents you’re dealing with, and the constituents’ families. As dean of Yale College you don’t — it makes it more difficult to navigate the conversation.”


Less than one year into his tenure, Holloway has already endured some exceptionally trying times. But Holloway also stepped into his role at a critical moment in Yale’s history.

The year 2014 saw not only a Yale College dean new to the role, but also a redefinition of that deanship. With the creation of the new position of dean of the Faculty of Arts and Sciences, currently filled by Tamar Gendler, the role of dean of Yale College was roughly split in half. Previous Yale College Dean Mary Miller spent nearly half her time dealing with issues of faculty promotion and tenure, a responsibility she split with the dean of the Graduate School. Now, these faculty concerns are Gendler’s domain.

This change brings Yale — which was formerly an “oddball” — into closer alignment with its peer institutions, Deputy Dean of Yale College and Dean of Undergraduate Education Joseph Gordon said. Most major research universities in the U.S. already had a dean of the FAS faculty by the time Yale shifted to the new model. As of now, nearly all of Yale’s Ivy League peers have a dean of the  faculty in some capacity.

Deborah Prentice, dean of the faculty at Princeton, said neither structure is superior; rather, it depends on the people filling the roles.

And the change was necessary, to some degree. Miller, who left the post last summer, explained that during her tenure, the faculty affairs time demand only grew. McKinley said it was hard to imagine how it was “humanly possible” to manage all of her duties.

Still, Biology professor Thomas Pollard, who served as Graduate School dean from 2010–14, said there were several advantages to the former structure.

“Our combined but very distinct expertise allowed us do a better job [governing faculty affairs] than either of us could have on our own,” Pollard wrote in an email to the News.

Even beyond the large shift in faculty governance, Gordon noted several other major structural changes to Holloway’s position. The creation of the Center for Teaching and Learning, which now includes several offices that were formerly governed by the YCDO, has lifted some responsibilities off Holloway’s shoulders.

And some changes were implemented even before Holloway stepped in. In 2012, University Secretary and Vice President Kimberly Goff-Crews’s position was created and took over some responsibilities formerly housed within the YCDO. A number of offices that used to report solely to the YCDO — such as the Office of Gender and Campus Culture — are now the shared responsibility of the YCDO and Goff-Crews, Gordon said. Goff-Crews said she and members of the YCDO work together closely on issues such as mental health policy and the cultural houses. Still, Associate Vice President for Student Life and Dean of Student Affairs Marichal Gentry said his role remains largely unchanged by the shifting responsibilities.

“Those are three major changes … and as far as I can see they’re all still works in progress,” Gordon said. “It’s not an exaggeration to say that almost every day thus far something has come up where people have been a bit unsure as to who has authority over a particular detail or a particular aspect of some process.”

Gordon, whom Holloway considers a mentor, has worked in the YCDO for nearly three decades and at Yale for even longer. But even with his long memory, he describes the structural changes to the Dean’s Office that were put in place in the past few years as “huge.” 

Similarly, McKinley — who attends many of Holloway’s meetings with him — said he does not remember seeing so much change all at once during his 20 years at Yale College. And Jane Edwards, dean of international and professional experience, described the present as a time of “unprecedented change” in this era of Yale’s history.

The structural changes to the YCDO took a great deal of work off Holloway’s plate, but hardly left it empty. Gordon said the dean would have more time to closely involve himself in admissions and financial aid policy, as well as in issues of pedagogy. For example, Gordon said that soon it will come time for a curricular review to better tailor Yale’s requirements and offerings to the 21st century. And with the University planning a roughly 15 percent increase in the size of its undergraduate student body with the two new residential colleges, Holloway will certainly have enough to keep him occupied.


The redefined role of the dean came at a welcome time; soon, Holloway will be responsible for even more undergraduates.

Chief among his responsibilities is planning for the two new residential colleges that will open in the fourth year of his term, a rare opportunity that might ultimately define his tenure.

“I know I’m not alone in making this a … top priority, but I think it will mainly fall to me to make sure that the two new colleges only enhance Yale,” Holloway told the News last May. “It’s going to be a fascinating challenge.”

But nearly a year later, little surrounding the new colleges has been made concrete — even if the colleges’ foundations along Prospect Street have begun to be poured. Students and faculty alike continue to express concerns about how Yale College will accommodate hundreds of new students without compromising already strained campus resources — from physical spaces to teaching resources. Throughout the year, professors and students interviewed have called on Holloway to publicly provide specific details about the form these colleges will take.

While part of his role is to ensure that all of these concerns are being considered, many of these long-awaited answers are simply not Holloway’s to give. Naming the colleges, for example, is a process Holloway is entirely uninvolved in. That charge falls to the Yale Corporation.

Similarly, the issue of faculty hiring has come under some fire this year. The discussion is especially contentious given the University’s assertion that the ladder faculty will not grow, as it grew in advance of the colleges’ opening.

“When the University says we’ve already hired all these professors, I think some attention needs to be given to how much all those professors are actually involved in the teaching of undergraduates,” senior French lector Ruth Koizim said. “What are we going to do to educate [800] more students?”

And English and American Studies professor Wai Chee Dimock described the new residential colleges’ effect on undergraduate and graduate education as “a question that would benefit from more extensive conversations.”

Gendler’s office will take the lead on this issue, working with Provost Benjamin Polak, Holloway said.

But other issues with the residential colleges fall squarely within the purview of the YCDO. This semester, for instance, Holloway has begun to work on a review of the college’s advising system, with the hopes of implementing improvements prior to the opening of the new colleges.

This semester, the work of Holloway’s six-member staff working group and larger steering committee has focused on issues of peopling and advising the colleges. The working group has presented to the steering committee their recommendation for how to populate the colleges. After consulting with the steering committee, which is a larger body consisting of students, staff, alumni and faculty, Holloway will work with Polak to determine a final plan.

But much of this work takes place behind the scenes, which perhaps explains why many on campus remain frustrated with the limited information they have surrounding the new colleges.

And still more is yet to come. With more than two years to go before the colleges open, many major issues, including teaching and advising, will not be firmed up this semester. But Holloway said several of these considerations — the new masters’ budgets, for example — will be made concrete during the upcoming academic year.

“It’s amorphous, I must confess, and one has to have a large capacity for uncertainty during a time like this,” he said. “But I do think for me, it’s feeling less amorphous with each month.”


When three new deans — Holloway, Gendler and Graduate School Dean Lynn Cooley — stepped into their offices this year, Holloway was the one working with the most stable circumstances. While Cooley dealt with staff transitions and Gendler navigated an entirely new position, Holloway was “steady as can be.”

But three months later, departure announcements began to flow in.

This year, the YCDO has lost several crucial players. Former Associate Dean of Yale College and Director of the Teaching Fellow Program Judith Hackman left this spring after 40 years at Yale. Former Dean of Summer Sessions and Special Programs Bill Whobrey left for Stanford in January. Gordon also announced in January that he would retire one year later.

Further, Director of the Afro-American Cultural Center Rodney Cohen resigned this term after students repeatedly demanded his removal. That left the YCDO with three searches for cultural house directors. And most recently came the announcement that Gentry will leave his post for Sewanee at the end of this academic year.

Holloway said it was these staff departures, among other unforeseen circumstances, that prompted an internal review of the YCDO, which is still ongoing.

“[That examination] wasn’t even close to being on my agenda, but is one of the most important things we’re doing right now,” he said. “So circumstance forced my hand there.”

The internal review will yield greater clarity on the YCDO’s shape moving forward. But perhaps the biggest change to his position — the amount of time he now has to interact with students — is already obvious. With his desk free of the “stacks and stacks” of faculty tenure and promotion materials that littered Miller’s, Holloway has more time to focus on what many see as his key constituency.

During her tenure, Miller attended a great deal of artistic, cultural and sporting events. Even still, she missed the one-on-one face time she had with students as the master of Saybrook College. After she became dean, there was “simply not time in the day or evening” to develop those relationships broadly, she said.

McKinley said that while Miller made herself very available to students, Holloway has even more time now to build on her work.

“[Some] time has been freed … so I’ve been working to find a way to do the thing I love the most, which is interact with students,” Holloway said. “Function followed form.”


When Lillie Lainoff ’17 arrived at the JE dining hall for lunch with Holloway last month, she was expecting to talk policy. Instead, the meal was accompanied by the kind of conversation “anybody would have over lunch,” Lainoff said — spring break stories, personal lives, academic interests. An hour later, Holloway had memorized the names of the dozen or so students seated around the table and shared with them some of his anxieties about his new role. He also revealed his true motives for the meeting.

“He said [the meal] was mostly for ‘his own selfish purposes,’” Ye Seul Byeon ’16 said. “He really enjoyed interacting with students as master, and missed getting to know students on a one on one level.”

On Wednesdays, between dozens of other obligations, Holloway squeezes in one of his favorite meetings of the week — a meal with undergraduates he calls “Lunch with Dr. J.” Each week he dines with a different student group — members of one residential college, students involved with the cultural centers, undergraduates in service groups.

“I’m proud to say it was my idea,” Holloway told the News in October, shortly after the practice began. “It seemed silly — I could [go] all week long [without seeing students]. I had to take some sort of proactive initiative. And I was nervous — I didn’t know if people would sign up.”

He need not have worried. When the opportunity was first offered in the fall, 108 spots were available for nine lunches. Within hours, 400 students had entered the lottery.

But not all students have been consistently impressed with Holloway’s efforts to engage. At a mental health forum in February, Yale College Council president Michael Herbert ’16 challenged Holloway and other administrators to respond, point by point, to the YCC’s recommended changes to mental health policy. When Holloway did not acquiesce — he later told the News that he would not give into “litmus test politics” — Herbert told the administrator that actions like these made students distrust the University.

Earlier this month, the YCC announced that Holloway and Director of Yale Health Paul Genecin had accepted several of the group’s proposals.

Others — such as Casey Lee ’17, a student active in the Asian American Cultural Center — are still asking for more, despite the measures that have already been taken during Holloway’s tenure. Following the cultural house review, for example, the University announced several renovations that will be made to the centers. But Lee said the renovations the University announced were insufficient, as the AACC needs an entirely new space.

But opportunities like Holloway’s lunches have given students the chance to better understand the difficulty that accompanies administrative positions, according to students who attended.

“Behind the administrative job is a human being — that was the main part for me, seeing how difficult it is to respond from an administrative perspective,” said Abhinav Menon ’18, who attended one of Holloway’s lunches in March. “The administration, especially Dean Holloway, takes a lot of flack from students … Students see one piece of the pie. More interaction with administration opens you up and makes you mature in the way you make demands.”


On the evening of April 11, Holloway stood on a stage in the New Haven Cooperative Arts and Humanities High School, arms raised in the “V” made famous by Alvin Ailey Dance Theater as he introduced the Yale Dance Theater’s yearly performance. He performed several steps of the famous dance, jutting his arms out to different angles and bending over at the waist, before speaking briefly on the importance of Alvin Ailey in the U.S. dance history and praising the dance group’s efforts.

His student engagement has taken more formal shape as well. When he first stepped into his new role, Holloway was surprised to learn that he was not required to attend any YCC meetings. This semester, he became the only Yale College dean in recent memory to have attended a YCC meeting, according to Herbert. While Holloway said it would be inappropriate to attend all meetings, he hopes to meet more with members beyond the YCC leadership in order to bolster the group’s importance.

While Miller met with YCC leadership formally only once per semester, Holloway meets with them once or twice each month. Danny Avraham ’15, who served as YCC president during Miller’s final year, said the addition of the FAS dean position was likely the primary factor in changing the amount of facetime the dean has with the YCC.

YCC Vice President Maia Eliscovich Sigal ’16 said Holloway seems to be more engaged than Miller was, though she acknowledged that she did not have the same perspective during Miller’s tenure.

“I think he is the best administrator we have at Yale,” Herbert said. “Every time we have brought a problem to him, he has either resolved it or he’s explained to us why it can’t be resolved.”

Soon after being named to the position of dean last spring, Holloway told the News one of his major goals would be to increase the transparency of the office — an adjustment, he said, that largely comes just from being present. This year, Holloway has hosted and attended numerous town halls and forums, on topics ranging from mental health policy to resources for the University’s four cultural centers, and launched reviews on many of the issues that students care about most.

Holloway confers with his colleagues on issues of student life in the residential colleges in monthly meetings with the Council of Masters — a group he knows well from his former role. Silliman Master Judith Krauss, the current chair of the Council of Masters, said that while it is too early to tell, she thinks the redefined position leaves the dean more time to approach big issues of student life.

Beyond changing policy to better meet student needs, Holloway has committed to instilling his values in the broader campus community.

“Holloway himself is interested in issues of community, civility, leadership and the ways in which we deliberate on issues of community-wide concern,” Gordon said. “That’s a kind of thing that every dean of Yale College has done, but he wants to bring much more to the forefront — more deliberately.”

In February, Holloway hosted a day-long leadership summit with Citizen University, a non-profit that promotes community-building and leadership in civic life, alongside Eric Liu ’90, the organization’s founder and CEO.

The idea was originally born out of conversations with University President Peter Salovey, but Liu said when Holloway became involved, he “got it immediately.”

“He practices what he preaches — he is the kind of citizen leader and open-minded, tough-minded creative framer of problems and solver of problems that he’s trying to get more undergraduates to be themselves,” Liu said. “[Holloway] understands what Yale’s job is — which is to prepare people for greater service in the wider world. He understands that deeply.”


When he first began the job of dean, Holloway gave his executive assistant a strange request: one hour a day that she was not to schedule. But important meetings arose, and the rule did not survive for long. Ten months later, the compromise has been stretched out even further. Weekly lunches with students remain sacred, but a lot else — including Friday morning basketball, and his academic work — has largely been put aside in favor of administrative responsibilities.

If you ask most students what the role of an administrator entails, they are likely to get it wrong. Part of this confusion likely stems from the enormity of his job description, perhaps best communicated by a quick scroll through Holloway’s packed iPhone calendar. His position, it turns out, is all-encompassing.

As Yale College dean, Holloway is responsible for just about every aspect of the undergraduate experience; the addition of Gendler’s position eliminated some major demands on the dean’s time, but in large part those hours have been filled by increased student engagement and the challenge of planning for the biggest expansion of Yale’s undergraduate body in decades. Each flick of his thumb reveals another duty.

“It’s breathtaking at times,” he said. “Registrar meeting. Executive committee of FAS Steering. Programs for minors. Liability issues. Meeting with parents, Course of Study Committee, development work. YCC meeting. Charging committees.”

There are also some unexpected quirks, he adds. “It’s a lot of eating, in my job — going to receptions, honoring different groups.”

The role of an administrator was never one Holloway actively sought. A decade ago, when he stepped into the role of Calhoun master, he told the News that he had “never imagined” being offered such a position. But after the surprise — and a year during which he describes the learning curve as “practically vertical” — Holloway found that he was well suited to an administrative role. And, perhaps more importantly, he realized that he found it rewarding.

Historians spend years on their projects, even decades. After spending the beginning of his career studying African-American history, Holloway found the idea of conceiving and completing a project within a semester or even mere weeks exceptionally gratifying.

“I got hooked on the idea. It brought me pleasure,” he said. “I was also discovering that basic ideas, even ethos — the way I was raised — translated very well into being a master: to set standards for a community, to take care of one another.”

As dean, it remains difficult to keep an active research agenda, Holloway said, and he hopes that when he returns to full time academia he will not have lost track of the field. He does what he can to maintain a teaching role. Although it is unlikely that he will take on any new advisees in the future, he is currently still advising a handful of graduate students who are close to or already working on their dissertations.

And he remains a teacher at heart. When faced with amateur questions about the University’s endowment, he is likely to simplify without condescending and explain using easy numbers and chicken tenders analogies.

Less than a year into his tenure, Holloway is not prepared to speculate on what he will do at the end of his five-year term. But his focus for the next four years seems clear.

“I know there are lingering hurt feelings or frustration over perceptions that the YCC or students aren’t listened to. But students are really listened to here,” he said. “The fact that they don’t feel they’ve been listened to is a failure of communication along the way. I’d like to do what I can to change that.”