MacGregor Cup Awards

Tam Matthews’s leadership brought a higher level of trust, collaboration and engagement to the community at West Point Grey Academy. As WPGA head from 2013 to 2019, Mr. Matthews invested deeply in his teachers’ leadership capabilities through exceptional programs in teacher evaluation, coaching development, and mindfulness-based stress reduction. Mr. Matthews commissioned Roy Group in 2015 to position WPGA’s senior leaders to powerfully develop the entire team’s competencies in coaching, providing feedback and practicing continuous improvement in leadership. Merging the high standards and intense drive gleaned from his years as an Olympic sailing champion with significant notes of warmth, compassion and belief in others’ potential, Mr. Matthews leaves a legacy of unity at West Point Grey Academy — and the highest employee satisfaction among all 120 independent schools across North America over 15 years’ worth of surveys by Lookout Management. Noted for his humility and tenaciousness in sticking with a team-wide movement toward elevating people to be their finest selves, Mr. Matthews exemplifies the MacGregor Cup’s key quality of leadership.