Four early childhood education teachers, two veteran and two newer teachers, were asked to pilot the use of handheld Personal Data Assistants loaded with Childchart assessment software. The participants were observed in their use of the electronic devices for monitoring student performance and interviewed regarding the use of the devices and their implications for assessment of early childhood learners. Veteran teachers indicated differences in both the use of the software programs and the style in which assessment activities were completed compared to newer teachers. The results indicate the need for professional development of new technologies to focus beyond the utilization of software and hardware and that new technologies implementation may be the catalyst for improvements in assessment strategies.