Mr Gregory was elected to the executive of the National Union of Teachers in 1898 having been described in the manifesto as "a genuine indefatigable". One of his main concerns was the plight of the trainee pupil-teacher employed for reasons of cheapness rather than efficiency, and the poor quality of education in rural schools which was a consequence of this policy. He was also concerned that girl pupil-teachers should have equal educational opportunities to their male counterparts. He gave evidence to a Royal Commission on the subject, pleading for a relaxation of some stringent examinations. A lawyer told him, sarcastically, that he had great faith in human nature if he imagined that young people would work except under the stimulus of examination. His reply typified his concern for the individual, his pride in his profession and his lifelong contempt for needless bureaucracy. . . .
"If they would not, they are not worth having as teachers".
As a teacher, Mr Gregory was outstanding. Brightwell Village School was a modern building when he began his own education and first served his pupil-teacher apprenticeship there under the Headmastership of George Ford Reely, a relative of his future wife. After some training and serving as an Assistant Master at Highgate Board School, London, he returned to more congenial rural surroundings to teach at the small Aston Rowant Village School, near his parent's Berk. shire home. He was Headmaster of the school at North Cadbury, Somerset from 1883-1889. The larger, and partly newer, school of the nearby market town, Castle Cary, became his from 1890-1901. The discursive style of "The Story of Royal Eltham" is apparent in the very detailed logbook he kept at Castle Cary School. A school photographer captured his likeness for posterity standing, hands in pockets and cloth cap on his head, beside his class of 40 boys of Standards V, VI and VII. Despite a full daily timetable he also gave support and occasional lectures with a Magic Lantern to an Adult Evening School in the building. Her Majesty Queen Victoria's inspectors reported that Castle Cary was "a thoroughly well-taught school". But inspectors always have to complain of something.. . .
"Sept. 14th 1897 Excellent organisation and first rate results. I think perhaps the room might be kept a little tidier."