It is widely recognised that technology, including social media, has many positive benefits in education although online technologies, particularly imprudent use of social networking sites, may also present problems for those seeking employment as a newly qualified teacher (NQT). To counter this, trainee teachers are provided with guidance on the use of social media however, it could be argued that the perceptions surrounding appropriate use of technology and social media are subjective and different stakeholders may hold a range of views regarding what is and what is not acceptable. This study aims to investigate differences in the values and attitudes of trainee teachers at the point of seeking employment in relation to those of head teachers as employers. The potential for a mismatch between these views and the subsequent negative outcomes for trainees is clear and an improved understanding of these differences could help teacher educators support trainees in specific aspects of their online presence. A survey of trainee teachers and head teachers was conducted and the data was analysed to identify key variations in values and attitudes in relation to social media posts.