Leading People to Greatness

Coach Paul Assaiante is the winningest coach in college sports history. For 30 years until announcing his retirement at the end of this season, Coach led the Trinity College squash program to 17 national championships and 20 finals appearances in the last 25 years, including at one point winning 252 straight matches and 13 straight national titles.

In his final season, Trinity’s squash team entered the national championships with the #6 seed and rode an almost fairy tale bookend to Coach’s career to the finals and within a single point of an 18th national title. Paul also coached the USA National Team in squash for 17 years, Trinity’s men’s tennis squad for 24 years, and World Team Tennis with Billie Jean King in its heyday. In 2010, he authored Run to the Roar: Coaching to Overcome Fear, one of my favorite books on sports and leadership.

Perhaps what is most fascinating about the soft-spoken Coach is he knew nothing about squash when he got his first coaching job. His true expertise is in managing, motivating, and inspiring a diverse group of players to be the best version of themselves.

Our conversation covers Coach Paul’s path and a career’s worth of wisdom about preparation, emotional regulation, managing high-performing individuals on a team, diversity, facing fear, learning to win and lose, and applying the lessons to the business world and next generation.