His teaching career began in 1977 at Augusta Park High School in South Australia. He was Assistant Senior Resident Master and head of history at Prince Alfred College, Adelaide and during this time spent a year at Felsted School in Essex, England. He was Deputy Principal of Ballarat and Clarendon College from 1990 until 1992. In 1993 he became Headmaster of Trinity Grammar School, Victoria. Whilst at Trinity he was interviewed by The Sunday Age in an article on corporal punishment and discussed the changes in attitudes in independent boys schools since the 1960s, having experienced them first-hand as a student and teacher; During Crawley's time at Trinity, the school became a world leader in the use of computers in schools, mandating each student have a laptop. He approached Microsoft about using their Officesoftware package for his students, instead of the then-standard schools package. A year later, Microsoft had released Office to schools worldwide and made a film about Trinity's ideas for integrating technology with education. Bill Gates sent Crawley a personal letter thanking him for his ideas on the use of laptops in schools. Crawley was also invited to Japan to address the board of Toshiba about the use of technology in schools. In 1999 Crawley moved to Sydney as Head of Knox Grammar School. As Knox's sixth Headmaster, he is credited for "bringing the School into the 21st century with an innovative program of technology and computer-based learning." He left to Knox to become managing director of an educational firm, Creative School Management. In 2006 Crawley moved to the Gold Coast to become principal of St Hilda's School, their first male head of school. During his time at St Hilda's they became one of the first schools in the world to adopt the iPad as a teaching and learning device. He retired from St Hilda's at the end of 2016. In 0ctober 2019 he was appointed the interim Principal of The Glennie School in Toowoomba, Queensland. Crawley was awarded an honorary doctorate for services to education from Griffith University. Griffith described him as "one of the pioneers of using computers and tablets in the classroom".
Publications
With Philip Cummins and Eric Bernard, Crawley has published the following educational books;
Managing risk in your school, Woollahra, NSW: Circle, 2011
Staff evaluation and goal-setting, Crows Nest, NSW: Circle, 2010