Driver training and education initiatives are often considered the cornerstone of many organisational fleet safety approaches, however there is currently little evidence regarding the effectiveness of such interventions. Similarly, the evidence regarding the value of other programs such as driving incentives also remains mixed, as fleet managers search to identify cost-effective methods to reduce the burden of fleet crashes. This paper reports on the development and implementation of a driving diary within a fleet setting that aims to increase personal insight and safety through the identification of aberrant driving behaviours. The driving diary is based upon brief intervention techniques used successfully in the health care arena over the last twenty years, and thus the tool aims to reduce engagement in unsafe driving practices. The driving diary is currently being trialled with a large sample of fleet drivers in Queensland. Drivers are being asked to keep a driving diary for ten days, noting times and places associated with unsafe driving behaviour. A follow up survey and formative focus groups is underway to determine the relative effectiveness and utility of the intervention in a fleet setting. It is hoped the intervention will prove to be a time limited, low cost, evidenced-based tool that can influence behavioural change. In addition, it is anticipated the results of this project will add to the body of knowledge regarding fleet safety, particularly the driver behaviour change literature. This paper will further outline the major advantages and pitfalls associated with developing safety interventions within the fleet industry, as well as provide direction for future research-based initiatives