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Liggett began his career in education over 30 years ago. He holds an honours B.A. and BEd from York University and began his teaching career in the 1990s with the Toronto District School Board. Before shifting to the independent school system, he returned to school, completing his MBA. from the Schulich School of Business. He then spent a few years working in the private sector, managing a confectionary manufacturing company, which means he knows more about candy than most of his students. 

He then returned to education through the independent school system, teaching first at St. Clement’s School in Toronto and then at St. Michaels University School in Victoria, B.C. “My experience in both public and private education, plus the private sector, has been very valuable to me in my current role. You never know what you’re going to be doing from minute to minute when you’re leading a school. The responsibilities are complex and varied.” 

Liggett’s passion for education comes from his enthusiasm for engaging young people in the possibilities of the future. He believes that great schools don’t only maintain strong academic standards but engage the whole student as a person. 

Liggett became head of school at The Country Day School in 2011, one year before the school embarked on its largest capital campaign in its history, creating a stunning dining hall, cyclone dome, and an updated Senior School. He credits his predecessors for bringing the school to a very solid place both financially and academically before he arrived. “I’m grateful to those who came before me for shaping the community ethos and student-centred pedagogy. Over the last decade, we’ve continued to evolve our academic and extracurricular programs, but also maintain them, because nothing was broken when I started here.”

When Liggett joined The Country Day School, his two sons did too. His oldest began in Grade 9 and his youngest Grade 3. Both have now graduated from the school. Being not only the head of school but a parent as well gave Liggett a unique perspective on the school. “One of the most important draws for me shifting my career to independent schools was the opportunity for my kids to attend. I chose to be in this sector because I’m a dad, too, and I value nothing higher than putting my children’s future interests first, as all our parents do. It’s an amazing life pursuit to participate in the growing up of children into wonderful adults.” 

While Liggett misses teaching, he seeks opportunities in his current role to connect with students, joining them on a field trip when he can. He makes an effort to get to know every student. Liggett may not act like a typical head of school. “I think the kids know that I'm not the archetypal strict, disciplinary principal. I ride a motorcycle, for Pete’s sake. I always say hello to them and I’m pretty much smiling all the time. So, there's that a little bit of apprehension, but mostly I think their attitude is, ‘He's pretty cool. He stays out of our business and we stay out of his business, and he keeps the school running.’”

Liggett is known by students and faculty as being friendly and fair. “I lead pretty much with my heart.” Liggett takes a big-picture view of students’ development. “Every day, kids fail wonderfully and they achieve wonderfully. We see all parts of the spectrum. I need all of my wits about me to manage that, but I also need to lead with my heart in seeing the whole child and guiding them through the inevitable struggles of growing up.”

He lives up to the school’s motto “Education with Balance”; providing students with a variety of opportunities to explore their interests inside and outside the classroom, allowing students to ask the question ‘Who will you be?’. The Country Day School aims to create a supportive and inclusive environment where students feel confident enough to pursue their individual passions. “We work hard here to strengthen that intangible sense of comfort for students, where they feel safe and cozy and want to come to school. When they feel like that, they’re ready to go—ready to learn and grow.”