The aim of this study was to measure the readiness of supervisors to utilize technology and online learning platforms for teachers’ plans and professional development during the COVID-19 crisis. To achieve this aim, the researchers developed a questionnaire comprising of 55 items based on the instruments used in pertinent studies. A mixed-methods research design was employed, whereby a quantitative online survey was supplemented by focus group discussions with selected supervisors. Survey data was subjected to One-way Analysis of Variance and t-test, while information obtained via focus groups was coded to identify common themes related to the obstacles and challenges supervisors face. When completing the survey, supervisors approached proficiency using technology; however, focus group discussions revealed misconceptions related to e-leaning and limitations in their ability to use technology in schools, as well as obstacles imposed by the structure and management of the educational system. These findings indicate that supervisors need support in acquiring the competencies required for integrating technology in education, and that their support to teacher community needs to be grounded in clear and systematic approaches and best educational practices.