Active listening is important for effective interpersonal communication, a prerequisite for successful teaching. The presented cross-sectional study examined personal and work factors associated to active listening in 3.995 Greek schools’ educators of all teaching levels and specialties. The study questionnaire posted on official and main teachers’ portals included personal and working data items, the Active Empathic Listening Scale (AELS), and the Active Listening Attitude Scale (ALAS). Multiple linear regression was used to identify independently associated factors with AELS and ALAS dimensions, and standardized regression coefficients were performed to measure the effect of independent variables. Regarding AELS, gender had the greatest effect on the Sensing subscale, followed by age and mental health promotion training. Years of teaching had the greatest effect on Processing subscale, followed by higher studies. Gender had the greatest effect on Responding subscale, followed by age, higher studies, and mental health promotion training. Concerning ALAS, mental health promotion training and support from colleagues had the greatest effect on Listening attitude subscale, gender and mental health promotion training had the greatest effect on Listening skill subscale, and gender, age, and years of teaching had the greatest effect on Conversation opportunity subscale. The identification of enhancing factors like training in mental health promotion could significantly contribute in designing training that can simultaneously benefit teachers’ skills and students’ psychosocial well-being.