His entry into diving coaching was by accidental chance, when he was asked to judge a gymnastics competition which included Judy Stewart, then a gymnast who impressed Webb with her ability. Reflecting on that time, Webb recalled that he "got a kick out of being involved, and before I knew it, I was coaching Judy on the trampoline". Initially, he would divide his time between coaching gymnastics and diving, before concluding that Stewart, by then his student, would have a better career chance in diving and he chose to fully commit to dive coaching. He had been coaching Canada's Olympic and national diving team in the 1960 Summer Olympics in Tokyo, although remarked that had considered marking 1968 as the end of his coaching career.
