Our Partners

Chris co-founded Educational Directions in 1986 following a career as an administrator, teacher, coach and dorm parent in independent schools. He has served as lead consultant to 150 head of school searches at schools throughout the country. Chris is a graduate of Roxbury Latin School, Brown University and Trinity College and is a past trustee of Cate School (California) and the Peddie School (New Jersey) as well as several non-profit organizations within his local community, including New Bedford’s Alma del Mar Charter Schools. Avid golfers, tennis players and anglers, Chris and his wife, Trish, — a past trustee of Wheaton College, The Posse Foundation and Milton Academy — reside in Mattapoisett, Massachusetts, where they enjoy family gatherings with the families of their three grown children.

Over the course of his career, Matt has developed a wealth of knowledge and information about Catholic schools. His BA and Masters from California State University are in the field of Linguistics. His doctorate from the University of San Francisco/Institute for Catholic Education Leadership is in Private School Administration with a specific focus in international education.

Matt began his teaching in higher education with the California State University and from time to time, has returned to that world as lecturer at Los Angeles Valley College, and professor at Senzoku Gakuen College, Japan and Troy State University, Korea and Hawaii.
 
His experience with independent Catholic schools includes teacher and associate dean of students at St. Vincent’s High School (CA); teacher, coach and Director of the International Student Program at Flintridge Sacred Heart Academy (CA), and academic dean at Marymount High School (CA) and middle school head at San Domenico (CA). Before joining Educational Directions, Matt served as Head of San Domenico School -  a day/boarding school founded by the Dominican Sisters, coed day in grades PK- 8 and girls only boarding/day in grades 9 -12 for 10 years.   Among his accomplishments were the creation of a Master Plan, the new construction of a science and technology center, hall of the arts and athletic center, and the installation of one of the largest school based solar systems.  In addition, he was responsible for the creation of a new teacher mentoring program, implementation of Teaching Excellence/Broad Band compensation model to promote professional excellence for faculty, as well as the enhancement of best practices for faculty in such areas as integration of literacy strategies across the curriculum.

Recognizing the importance of education and being of service to the larger community, Matt has served on the board of Seeds of Learning, a nonprofit organization dedicated to improving educational opportunities in rural Latin America as well as a member of the Board of Directors of Academy of Notre Dame, Tyngsboro, Massachusetts. He currently serves on the board of Community Harvest, a nonprofit organization of the Kennebunks that works to meet the needs of the local community through various food programs, scholarship and financial assistance.

Born in Japan, Risa attended an international school in Tokyo until she moved to the States. After a career as a professional dancer, she entered the educational field, holding various teaching and administrative roles at institutions such as Flintridge Sacred Heart Academy, Marin Academy and San Domenico School.

At San Domenico, Risa began as an instructor of Japanese language before moving into the director of admissions position for the high school as well as for all international students. Her signature programs were known for attention to the individual prospective students and their families and for involving currently enrolled families and students in the process. In addition, as director of international student relations, a position proposed by Risa to focus on the needs of international families, she collaborated with members of the counseling, development and language departments to ensure that those families felt well-served by the school and part of the school community.

As a search professional, Risa brings the same care and attention to the schools she serves as well as to the candidates she guides through the search process.

In her free time, Risa enjoys scuba diving, yoga classes and taking her dogs out for numerous walks.

Risa holds a Masters in Asia Pacific Studies from University of San Francisco and a Bachelors in Japanese Studies from Dominican University.

In 1992 Peter Hutton became CEO of Beaver Country Day School, at the time a struggling under-enrolled under-financed school, and through creating a laser focused organizational culture built it into a school with the strongest brand of Boston area independent schools, and into one of the most innovative schools in the country. Hutton believes that strong leadership (Leadership is having a point of view) creates a high functioning organizational design that creates a culture passionate about vision, nimble about strategy and always meeting the needs of the customer. In Hutton’s organization 100% of employees must support the culture and mindset. His approach to turning Beaver around and making it a dynamic environment applies to any sector and any organization at any stage of development. 

At Beaver Hutton endeavored to reimagine education in the context of the future of work. Hutton is a strong advocate of embracing new technologies and designing physical spaces to both support and shape creative problem solving. To that end, Hutton has launched many initiatives with the goal of expanding the nature of school: founding partner of NuVu Studio, the rollout of a 1×1 laptop program, introducing Design Thinking, implementing The Coded Curriculum and, most recently opening the “Library of the Future” – a $20M Research and Design Center. 

Hutton has spoken at a wide range of venues and organizations including SXSW, Catalant, ATLIS, Boston Society of Architects, The National Association of Independent Schools and New England Association of Schools and Colleges. Hutton left Beaver in 2020 and now, in addition to consulting for Educational Directions, he works at the MIT Media Lab with the Center for Constructive Communication, and he consults with NuVu as well as Brainly and Sora Schools – both General Catalyst Partners backed companies.

He has run 5 marathons and biked 16 Pan Mass Challenges (so far) and, alas, is a lifelong Buffalo Bills fan.

Garet Libbey brings more than two decades of leadership experience in independent schools to her work in leadership development, executive search, and talent strategy. She partners with schools and mission-driven organizations to identify, support, and grow leaders who lead with clarity, purpose, and impact.

Over the years, Garet has held a range of senior administrative roles—including Middle and Lower School Director, Co-Chair of DEIJ, Assistant Head and Associate Head of School, and Chief Talent Officer. She is deeply experienced in designing and leading hiring processes across academic and administrative roles, creating competency-based systems, and training hiring committees to make inclusive, thoughtful decisions. She has advised Heads and leadership teams on talent development, organizational change, and building leadership capacity.

As the founder of Garet Libbey Consulting, she provides executive coaching and consulting to individuals, groups, and leadership teams—supporting managers, senior leaders, and Heads of School on strategic leadership, culture-building, and organizational effectiveness. Her work is grounded in a strengths-based, equity-informed approach to leadership.

Garet is certified through the Co-Active Training Institute (CTI) and the International Coaching Federation (ICF). A graduate of Williams College, she also holds master’s degrees from the Harvard Graduate School of Education and Seattle University. In addition to time with her husband and two teens, she loves to cook, garden, and spend as much time outdoors as possible.

As a teacher, administrator, and parent in the California Independent school community for 25 years, Shoshanna brings a uniquely holistic perspective to her role as a search consultant. Drawing on her deep expertise in diverse school cultures, she has partnered with schools across California and the Northwest to find educators who share their values and missions. Shoshanna has successfully placed over fifty educators in a variety of independent school roles across all levels. With a proven track record in identifying exceptional leaders, she excels at two-way matching, ensuring that both the candidate and the school are an ideal cultural and professional fit. Shoshanna offers multiple perspectives and a breadth of experience supporting day, boarding, and faith-based schools in searches ranging from division heads, directors of diversity, equity, and inclusion, advancement, technology, finance and operations, and assistant heads of school. 

Shoshanna holds a B.A. from Wesleyan University and a Ph.D. from Stanford University, with a background that includes teaching and leading programs at Stanford, USC, UCLA, and Harvard-Westlake School. Originally from Seattle, she splits her time between the Sacramento and Lake Tahoe areas and enjoys hiking, biking, and skiing.

Nicole McDermott (she/her) is an independent school leader, educator, facilitator, and certified leadership coach with 20+ years of experience. She values choosing courage over comfort, leading with transparency and vulnerability, building connection, attending to the details, and showing up with curiosity. For eighteen years, she led an award-winning Northern Virginia independent school (Pinecrest School, PK-6, 2005 – 2023) and brings this experience and her values and skills to Educational Directions to meet schools where they are, assisting and empowering them to reach their next level.

Nicole holds a B.S. in elementary education (with a minor in English/journalism) from Salve Regina University in Newport, Rhode Island, and a M.Ed. in education leadership from George Mason University in Fairfax, Virginia. Nicole was trained by Dr. Brené Brown as a Certified Dare to Lead™ Facilitator and has held this credential with pride since 2019, facilitating curriculum based on Brené Brown’s work, research, and best-selling book. Nicole completed an accredited coach training program at George Mason University and is an International Coaching Federation (ICF) Professional at the ACC level. Additionally, Nicole is a Gallup-Certified Strengths Coach, trained to help individuals and teams grow from and set goals around their CliftonStrengths assessments; a Certified Practitioner of the EQ-i 2.0 + EQ 360 emotional intelligence assessment tools; and a Certified Grief Educator trained by David Kessler. These designations support Nicole’s ability to identify well-qualified, mission-aligned, and emotionally intelligent school leaders. Additionally, through her own practice, Quality Matters, she co-creates transformative spaces to encourage professional and personal growth through executive coaching, leadership consulting, facilitating, and more with her clients.

Nicole’s approach is grounded in mutual trust, integrity, the importance of continuous growth and improvement, and the idea that we can hold two – or more! – truths at once.

A longtime and life member of Kiwanis International (beginning first with Key Club in high school), Nicole is a volunteer in her community and has worked with and managed volunteer teams delivering leadership content to teenagers. She is directly responsible for the logistics of an annual educational conference serving hundreds of high school students and their faculty advisors, and she has been a mentor and advisor to high school students serving in district leadership roles since 2003.

Nicole meditates every day, considers herself an emergent runner, donates blood regularly (O+), and listens to podcasts and audiobooks at 2x speed. In addition to volunteering, she spends her free time reading, walking, traveling, being near the water whenever possible, seeing musicals, staying connected with people she loves, and supporting causes that are important to her.

While Nicole grew up in Massachusetts, she has lived outside of Washington D.C., in Northern Virginia, for more than 20 years. With gratitude and awareness, Nicole acknowledges that she currently lives on the land of the Piscataway people; Nicole is committed to showing up as a learner and listener in the equity and inclusion space.

Mike joined Educational Directions in 2020, bringing decades of leadership experience to his role as a trusted partner to independent schools nationwide. Specializing in Head of School searches and governance development, Mike is known for his strategic insight, deep network, and ability to identify transformative leadership. His results-driven approach is matched by a genuine commitment to building strong, lasting relationships with search chairs, school heads, and candidates—helping schools not just fill a role, but find the right leader for their unique mission and future.

Before joining Educational Directions, Mike built a distinguished 44-year career in independent and international schools. He served as Headmaster of Pace Academy in Atlanta, Georgia, for eight years, and later as Head of School at Shorecrest Preparatory School in St. Petersburg, Florida, for fifteen years. Over his 23 years as a school head, Mike partnered with 13 different board chairs, developing a deep understanding of effective board leadership and governance.

Mike has also contributed to the broader independent school community through board service with the Southern Association of Independent Schools and the Florida Council of Independent Schools, where he developed a specialty in accreditation. His work with over 100 schools and heads has given him broad insight into the challenges and opportunities facing today’s educational leaders.

Outside his consulting work, Mike serves on the board of the Vanguard School in Lake Wales, Florida. He is also a Program Manager, mentor, and emotional intelligence coach with the Severn Leadership Group, an organization focused on leadership that highlights virtues and team building, headquartered in Annapolis, Maryland.

Mike holds a bachelor’s degree from the University of Dayton and a master’s degree from Miami University. In 2017, he was selected for the prestigious Head’s Cohort at the Klingenstein Center at Columbia University. He continues to live in St. Petersburg, Florida.

Meera’s approach to search combines her beliefs in the centrality of relationships with the value of well-designed systems, and she has a proven track record of guiding administrator searches that yield excellent candidates, strong process and community buy-in, and valued support beyond the placement. Meera has over two decades of experience as an educator and leader at boarding, day, co-ed, single-gender, 6-12, pK-12 schools, face-to-face, and online schools. As a consultant, Meera has successfully supported dozens of schools in moving their people and programs forward via Trey Education. With Educational Directions, Meera leverages her deep experience as an academic leader and administrator to partner with schools on program-facing senior administrative searches, ranging from Division Directors to Assistant Heads of School to Deans of Faculty & Academics–anywhere the focus is on strategic programmatic leadership that makes a difference!

As a search consultant, Highley has led searches for division head (upper, middle, and lower school), athletic director, enrollment management, and college counseling, while also supporting a number of head of school searches. He loves partnering with schools and their search committees in these searches that will positively impact students’ experiences.

Highley spent 30 years in independent schools as a teacher, coach, and administrator before becoming a search consultant. Right out of college, he returned to his alma mater (Severn School, MD) to begin his career as a middle school math and Latin teacher, while coaching soccer and lacrosse. Over the course of his sixteen years at the school, Highley transitioned to the upper school, where he taught English and algebra, and became dean of students, academic dean, and eventually the Upper School Head. After a stint as Head of the Upper School and Assistant Head of School at Chestnut Hill Academy in Philadelphia (now Springside Chestnut Hill), Highley moved to Thayer Academy in Braintree, MA, where he served as the Upper School Director for twelve years. While in schools, Highley especially loved building community and attracting excellent teachers to his schools.

Highley earned a B.A in English from Princeton University, where he was also a four-year member of the men’s lacrosse team. He later earned an M.Ed. in Administration and Supervision from the University of Virginia.

Residents of Charlottesville, VA, Highley and his wife Anne enjoy spending time with family, cooking, traveling, hiking, and enjoying the amenities that the Charlottesville and UVA community offers. They have two children, one in graduate school and the other in college.

Jay is a career independent school student, teacher, and leader. He served as the head of three schools in 17 years: Rio Grande School in Santa Fe, High Meadows School in Atlanta, and George Jackson Academy in New York City. Prior to becoming a head, Jay spent eleven years as the director of curriculum and a middle school humanities teacher at Far Hills Country Day School in New Jersey.

Jay has been active in the greater independent school world throughout his career. He has served on several boards, including the Southern Association of Independent Schools (SAIS) and the Independent Schools Association of the Southwest (ISAS). He has extensive accreditation experience, having led 18 visiting teams at schools across the country. He has written and presented prolifically, and has advised boards and heads on topics ranging from equity to best practices in governance and leadership.

Jay holds a B.A. in English from Guilford College and a Master’s in Educational Administration from Rutgers University. In 2017, he was awarded a fellowship to the Klingenstein Center’s Heads of Schools Program at Teachers College Columbia University. Along with spending time with his wife and daughters, Jay is an avid fan of live music and theater, and he’s always in search of a good fishing hole.

John Watson has worked with independent schools in governance, leadership development and executive searches through Educational Directions, Inc. since 2017. John was Head of School at Seacrest Country Day School (FL) from 2012-2017, and at West Nottingham Academy (MD), a boarding and day school founded in 1744 from 2002-2012. John holds a Bachelor’s Degree in Music Education from Northern Michigan University, and an MA and PhD in Music Composition and Theory from the University of Minnesota. During his thirteen years in the Twin Cities, John was an active composer and conductor as well as an educator. 

John began his independent school career at Breck School (MN), an independent Episcopal PK-12 school as co-chair of the Visual and Performing Arts Department. From 1992-2002 John served as Assistant Head and Academic Dean in three boarding schools; Darrow School (NY), Peddie School (NJ) and Cheshire Academy (CT). 

John employed a shared leadership style during fifteen years as a head of school at both Seacrest and West Nottingham, empowering the community to strive for clarity and innovation by engaging faculty, students, parents and trustees in deep, mission-centered exploration of programs. John believes that as a head of school, the most important role one fulfills is to help a school to embody its mission to the fullest, and that while change is inevitable, change driven by mission is the most likely to flourish and endure. 

John served for six years on the Association of Maryland and DC Independent Schools Board of Directors, and on several regional arts boards over the years. John and his wife, Bonnie, live in Brentwood, TN, ND have three children and five grandchildren in Brentwood, Los Angeles and Seattle.

Being raised by two educators, living on school campuses growing up, and working at schools across the country has given Lindsay a deep understanding of the value of independent education. 

Lindsay attended high school at Peddie School (NJ) and then obtained a B.A. in Art History from Vassar College (NY). 

Following that, she started her career in student enrollment at Conserve School (WI), traveling to 19 countries and numerous states across the U.S. to recruit students. She also worked at the French International School of Philadelphia (PA) where, in addition to admissions work, she redesigned the school’s website and produced other marketing materials. Lindsay then became the International Admissions Counselor at the University of St. Thomas (MN), serving as the main contact person for international and exchange students from over 20 partner institutions worldwide. Her most recent independent school role was as the Assistant Director of Admissions at The Center for Early Education (CA) where she was involved in all aspects of student enrollment. 

Lindsay lives in Los Angeles where she enjoys the many cultural and entertainment opportunities in her community, as well as traveling to new places.