Meet Our New Head of School: Dr. Timothy Cottrell

In fact, throughout this past spring and early summer, Dr. Cottrell was busy doing double duty by wrapping up his sixth year as Head of The Harley School, an independent, college-preparatory school in Rochester, New York, that’s home to approximately 520 students, while getting up-to-speed and taking over the lead reins at ‘Iolani with more than 1,800 students and a 150-year history. It was truly a hectic time for the incoming Head.

Yet if anyone can juggle multiple balls in the air, Dr. Cottrell can. He is credited with elevating The Harley School towards several major accomplishments thanks to his visionary leadership and experience. His impressive math and science background includes a broad array of experiences in communications, technology, engineering, teaching, and business ownership. He received a B.S. in Chemical Engineering from Syracuse University, and earned an M.A. and Ph.D. in Chemical Engineering from Princeton University. He is a rare and brilliant example of a combination of logic and imagination.

At first glance, nothing could be further from living and working in upstate New York than moving almost 5,000 miles across the continental United States and the Pacific Ocean to Honolulu to tackle a new leadership opportunity. Not to mention, the distinct cultural differences between life on the East Coast and in the Hawaiian Islands. But as they say, looks can be deceiving. So how did the life and experiences of Dr. Timothy Cottrell lead him to becoming ‘Iolani’s new Head of School?

The Right Fit

Let’s start at the beginning. In August 2011, following the announcement of Dr. Val Iwashita’s retirement, the school launched an exhaustive five-month campaign to find his successor. First off, ‘Iolani appointed Wickenden Associates, a highly respected national educational search firm, to handle the global hunt. Numerous applications were received from across the country and even Europe. Next, a Search Committee, made up of members of the Board of Governors, reached out to students, faculty, staff, alumni, parents, and other respected members of the ‘Iolani community to identify the qualities they were looking for in the school’s next leader. Those characteristics included vision, strong leadership, cultural fit and spiritual commitment. Submitted applications were reviewed with this criteria in mind, and in-person interviews were conducted with eight semi-finalists from Hawai‘i and the mainland. Finally, the three finalists and their spouses were invited to spend two full days visiting the campus and meeting with representatives of ‘Iolani’s various constituencies. Everyone who met with the candidates was asked to provide feedback, and comprehensive reference checks were also conducted.

Ultimately, in February 2012, the ‘Iolani School Board of Governors voted and unanimously approved the Search Committee’s recommendation for the incoming Head of School. After an extensive worldwide investigation, the Search Committee was satisfied that they’d found the right person for the job: Dr. Timothy Cottrell.

“Dr. Cottrell shares common values and common ideas about academic excellence and education as we at ‘Iolani believe,” says Ann Yoneshige, longtime teacher and administrator who is serving as Interim Dean of Upper School. “He believes in a very community based school. He’s a wonderful communicator and listener. He responds well to questions. He’s very bright and knowledgeable. He’s very curious and eager to learn. He has vision and he understands how to make that vision a reality.”

An Early Emphasis on Education

While growing up, Dr. Cottrell’s family maintained a home in Geneseo, New York, where the local high school he graduated from is located, but his family moved around a lot thanks to his father’s stable of racehorses. The senior Cottrell was a horse trainer and drove standard bred racehorses for a living.

“What I carry with me most from this experience is a strong work ethic,” opines Cottrell of his upbringing within this working class family business. “It was an early morning to late evening 365 days-a-year working lifestyle and very exciting for kids—from growing up on the grounds of race tracks to going to countless county fairs. Much of my time was spent grooming horses. My father’s stable colors were red, black and white. He’s very happy with the ‘Iolani hat I just gave him.”


Unlike most of his young peers who didn’t graduate from high school, Cottrell and his sister Tracy benefited from their parents’ commitment to maintaining a steady home base and stressing the importance of education. Both Cottrell children are first generation college graduates.

After high school, Cottrell followed his sister to nearby Syracuse University so he could study chemical engineering. He did well enough to attend graduate school at Princeton in New Jersey. As he recalls, it was there at that he found his true calling, and it happened to be teaching.

“I won a number of teaching awards from the Engineering Council and the Association of Princeton Graduate Alumni so I started tutoring local high school students. This went well and, as you would imagine, the Princeton area moms-network spread the word and pretty soon, after-hours, I was logging four to five hours a day, nearly seven days a week helping teenagers with their math and science. Then, in 1993, I completed my Ph.D. focusing on quantum semiconductor devices but it was the tutoring experience with students and my love for teaching that directed the course of my professional life.”

1993 marked the early stages of  digital media. It was a precursor to widespread use of the Internet and the term “multi-media” was the buzzword. He had the notion that experience of one-on-one education, tutoring, would be valuable intellectual property for the design of educational software that used rich media. So he founded Princeton Teaching Associations Software. Over the next six years, Cottrell’s company made award-winning interactive software on subjects ranging from standardized test preparation to Taoist philosophy. At this time, he also learned a great deal about project management, finance, marketing and communications.

“One of the great side benefits was that I got to work with faculty from Princeton-area schools, one of which was The Lawrenceville School,” says Cottrell. “During the development of a number of chemistry-related titles, I became good friends with the Dean of Faculty at Lawrenceville, who was a chemistry teacher, and she asked if I would be interested in teaching part-time at the School. This single section of AP chemistry was my first step into the greater world of independent schooling.”

By 1999, the “Dot Com” revolution hit the Bay Area and beyond like wildfire and eclipsed “multi-media” as the driving trend. A number of Cottrell’s friends had done remarkably well for themselves in Silicon Valley. They knew about his experience launching a start-up tech company and asked him to join them in building a new dot-com around the concept of a materials exchange for the grading and excavation industry. He accepted and got to work at around the same time that he married his wife Lisa. All the while, he continued to teach his lone section of AP chemistry at Lawrenceville.

A year later, in 2000, the fledgling tech company was up and running, the Cottrells were expecting their first child, and Dr. Cottrell was working bi-coastal. With the birth of their first son, Connor, it didn’t take long for Lisa to gently suggest to him that his professional routine was not conducive to a high quality of family life, and he was fortunate to have a new work opportunity present itself at Lawrenceville.

“At that time, the school had an opening for a top administrative position, Chief Information Officer, and the prospect of merging my love for education with a family life set on a beautiful campus led us to pursue this opportunity,” he says. “I was offered the job, left Silicon Valley, and joined the senior administrative team at Lawrenceville full time.”

Lawrenceville uses the triple-threat model. So, for the next four years, he taught, contributed to a residential life team and coached while leading the school’s technology and communications departments. “I was fortunate enough to have a wonderful mentor in the Headmaster at Lawrenceville, Michael Cary, and very soon after joining the administrative team, I started the process of working toward a school leadership position,” he says.

A Leader Who Rolls Up His Sleeves

In 2006, Cottrell accepted the role of Head of School at The Harley School in Rochester, New York, and now, just six years later, has moved on to his next great opportunity to serve ‘Iolani and its community.

“What makes Dr. Cottrell a great fit for ‘Iolani is his experience working as a Head of School, his core beliefs about best practices in teaching and learning, the fact that he really cares about this school and the people here, and finally his sense of wanting to be involved in what is happening at our school at every level,” says Dean of Lower School Gerald Teramae.

While his list of accomplishments is impressive, he also balances a busy home life with Lisa and his two sons, Connor ’20, entering the fifth grade and Sean ’22, the third grade. In his free time, he enjoys snowboarding, surfing, and gaming with his kids. He’s also an avid cook and fisherman logging hundreds of hours casting the inshore bite for fluke, striped bass, and bluefish, and the offshore bite for bluefin, yellowfin tuna, and mahi mahi. Staying active and fit is also important so he jogs daily, four to five miles a day, while catching up on books on tape or tunes into his favorite podcast RadioLab.

Admittedly, being the leader of a top independent school in today’s fast-paced modern world can be a challenging one. As a Head of School, one must wear many hats on any given day and assume many roles: the spokesperson, the decision-maker, the cheerleader, the kind parental figure, the disciplinarian, the enforcer of values, the steward of tradition, the advocate for change, and many more. In the end, it’s all about having the right tool for the job at hand. So what type of leader is Dr. Cottrell?

“At the core, I would consider myself as a values-based leader,” affirms Cottrell. “I believe that the expression ‘perception is reality’ is over-empowered in our society and tends to have leadership sway towards a political style. When I think of good leadership, I think of good judgment and this is based on a system of values and beliefs. It is important to consider perception and to work toward minimizing misperception, but at the end of the day there is right and wrong and this informs any leadership decisions.”

Fundamentally, the Head of School is the “buck stops here” person, but schools are complex relationship-driven communities so, in his experience, the more people who are empowered in a distributed leadership model, the higher the potential for the institution to achieve. This is a focus on the sum-as-greater-than-the-parts leadership style.

“When my boys ask me about my role as a Head of School, I tell them I am ‘the big helper,’ that my job is to help everyone do their best at their jobs,” he shares.

That said, Cottrell also enjoys being hands-on to a degree. To lead the faculty, he believes you need to roll up your sleeves sometimes and stand shoulder-to-shoulder with the team that’s around you. Yet it’s always challenging for any Head of School to find the time to teach, partner with faculty members and interact often, and in significant ways, with the student body.

 “I like ideas,” he continues. “I like to help bring ideas into reality and I’m interested in a wide range of topics from the arts to civic engagement to mathematics and science.”

People Make Schools

So what’s the secret to being a great Head of School and unlocking the potential of the institution and its students? Dr. Cottrell believes that there is one key ingredient to great leadership. First and foremost, it’s the understanding that schools are made up of people. The best of what education has to offer is built on strong one-to-one relationships. It’s also one of the reasons independent schools like ‘Iolani offer such a unique and exceptional educational experience. People with a passion for learning and teaching are here and are given the freedom to care about the growth of each and every student.

“These are places where so many look back and say, ‘That person really helped me become who I am,’” he notes. “You look to the past and this school is filled with those people, as it is in the present. We are communities built on a common cause that share a commitment to education of our children as one of life’s highest priorities. A good Head of School stewards the institution so that the people of the school, all of its constituencies, share in the life of the school and know that they are valued members of the community.”

Beyond the valuable influence of a school’s teachers, administrators and staff, he believes that a good Head of School must be a good communicator. At any great school, there is so much activity and achievement on a daily basis that it is hard to keep up. He understands that it’s the responsibility of the Head of School to make sure that all members of the school community share in the success stories of the school.

Additionally, Dr. Cottrell believes in a basic yet powerful truism: Schools grow best from within.


“I know it sounds like an oxymoron when thinking of a well-established school with its traditions and the momentum of historical practices. But within this, there is always a spark of innovation and creation,” he notes. “New growth always occurs with the special flavor and characteristics of the institution. There is certainly a necessary resonance with prevailing trends and wisdom from the external world in order to validate the merit of change. However, it’s the interpretation and incarnation of these ideas from the lens of the institution that holds the greatest promise for new ideas and practices to come to life.”

He continues: “At the end of the day, I think a good Head—alongside the faculty—shares a love of kids, learning, teaching and the belief that education holds the key to the future of those for whom we care and the larger world around us.”

As a result, being a conscientious member of a larger world means giving back to the local community. And Dr. Cottrell understands that public service is an essential element for the successful future of ‘Iolani and its students.

“I believe that schools define themselves not only by their academic excellence but also by the works of good that they foster in the world,” he says. “It is often the case that such good works add a dynamic element to our school communities that builds student and faculty leadership, diversity, relationships with the surrounding community, and the skills that our students need to be global citizens.”

How about any final words of wisdom for the new Head of School from the man who previously held the post?

Dr. Val Iwashita reveals: “One of the best bits of advice I received was from David P. Coon, who served as Headmaster here for 22 years. He advised me to, ‘Be your own man.’ Leading any organization can be difficult; leading one as prominent as ‘Iolani, especially one that encourages diversity of thought and action is extremely challenging. Keeping your own counsel is critically important.”

“He should take the time to get to know the community by both talking and listening,” says Jenai Wall, Chair of the ‘Iolani Board of Governors. “Get his family acclimated to their new surroundings. He has a style that will help him here. He wants to hear from the community and fit in and help others achieve their goals.”

Fellow member of the ‘Iolani Board of Governors Lisa Sakamoto chimes in: “I told Tim to enjoy the road ahead. His family will be an exciting part of that journey. We are lucky to have him and he is lucky to be coming to a school with great traditions like ‘Iolani.”

“For Tim, I think he believes that this is a golden opportunity. And we feel extremely grateful and blessed that someone of his magnitude is coming here,” Sakamoto adds.

In many ways, a myriad of experiences and achievements have all led Dr. Cottrell to where he is now: Home in Hawai‘i at ‘Iolani School.

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